The 100 Best Romantic Comedies of All Time

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The 100 Best Romantic Comedies of All Time

As a genre, the romantic comedy has had pretty sharply defined highs (the 1940s and 1980s) and lows (1990s-2000s) based on viewer appetite and studio competence, but thanks to this thing we call “the human condition,” hope-laden fables showing how two people can, indeed, find and cherish one another despite all obstacles will never stay out of fashion long—no matter how soulless and cynical the industry. Whether because we are young and naïve, not-so-young and searching, or old and grumpy with a soft spot (or wistful memory), there’s always an appetite for fascinating meet-cutes, resolved comedies of errors and melted gruff exteriors. So no matter your particular poison when it comes to scripted takes on love and relationships, let Paste’s list of the 100 Best Romantic Comedies of All Time provide you just what the doctor ordered.

Of course, while romantic comedies come in as many flavors as romance itself, this list is somewhat more limited, drawing mainly from Hollywood (though we’ve sprinkled in a few Bollywood classics by way of acknowledgement). Also this important reminder: more than a few grand, successful rom-com gestures will just yield stalking charges and restraining orders when applied in the real world, so use a little common sense, why don’t ya?

Here are the 100 best romantic comedies of all time:

100. Trainwreck (2015)
Director:   Judd Apatow  

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Think of Trainwreck as Amy Schumer’s comedy fed through Judd Apatow’s directorial dehydrator: It’s 124 minutes of everything we love about Schumer deprived of just enough bite and flavor to keep us tantalized, and not enough to make the experience special. To the credit of both Apatow and Schumer, who wrote the whole damn thing, they’ve made a funny film—and in fairness, “funny” is all that Trainwreck needs to be. The film’s protagonist is Amy (Schumer), a New York gal who parties hard, sexes harder, and works at a trashy guys’ magazine run by walking tonic Tilda Swinton. Amy doesn’t like to keep a man for too long, preferring to keep a rotating stable of dudes on tap. But life rears its ugly head when Amy, on assignment, interviews Aaron Conners (Bill Hader), a successful sports doctor who begins a-courting her. When the picture clicks, you’ll be too busy laughing to worry about politics. Schumer and her colossal supporting cast easily prove that all anyone needs to cut together a solid comedy is good old-fashioned chemistry, sharp delivery, and a surfeit of killer punchlines. —Andy Crump


99. Love Actually (2003)
Director: Richard Curtis

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When it comes to portraying love confessions of all varieties, very few can beat the kind on display in Richard Curtis’s epic Love Actually. In one of its many romantic threads, Juliet (Keira Knightley), a recently married woman, has just discovered that her husband’s best friend Mark (Andrew Lincoln) has been nursing a secret crush on her. One night, he arrives at their front door and silently delivers his long-repressed feelings via hand-drawn cue cards. While certainly sweet and heart-warming, the inherent sadness that pervades this scenario—such a relationship can never work out between the two—prevents the exchange from being overly saccharine. —Mark Rozeman


98. The Lobster
Director: Yorgos Lanthimos

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Greek director Yorgos Lanthimos’s follow-up to international break-out Dogtooth ditches that film’s knotted familial pathology, but refuses to be any less insular. Instead, it expands, even bloats, Dogtooth’s logic as far as it’ll stretch. I know: That doesn’t make much sense, but stay with me—which is exactly how Lanthimos and co-writer Efthymis Filippou assume the audience will approach The Lobster, starting with the familiar, leading man visage of Colin Farrell, gone full dad-bod for a role that is debatably the actor’s best example for his still unheralded genius. With a remarkable dearth of charm, Farrell inhabits David, a man who, upon learning that his wife has cheated on him and so must end their relationship, is legally required to check in to a hotel where he has 45 days to find a new mate, lest he be transformed into an animal of his choosing. David easily settles upon the titular namesake, the lobster, which he explains he picks because of their seemingly-immortal lifespans, the creatures like human ears growing and growing without end until their supposed deaths. At the hotel, David tries his best to warm to a beautifully soul-less woman, knowing his remaining days are numbered, but the depths to which she subjects his resolve eventually encourages him to plan an escape, through which he matriculates into an off-the-grid conglomerate of single folk, led by Léa Seydoux. There, of course, against all rules he has a meet-cute with another outsider (Rachel Weisz) involving elaborately designed sign language (a metaphor maybe, like much in Lanthimos’s world, for the odd ritual of dating), and they fall in love. The world of The Lobster isn’t a dystopian future, more like a sort of mundane, suburban Everywhere in an allegorical alternate universe. Regardless, Lanthimos and Filippou find no pleasure in explaining the foundations of their film, busier building an absurdly funny edifice over which they can drape the tension and anxieties of modern romance. In that sense, The Lobster is an oddly feminist film, obsessed with time and how much pressure that puts on people, especially women, to root down and find someone, no matter the cost. If you’ve ever had a conversation with a significant other concerned about the increasing dangers of becoming pregnant in one’s late 30s, then The Lobster—and its ambiguous but no less arresting final shot—will strike uncomfortably close to the home you’re told you should have by now but probably can’t afford. —Dom Sinacola


97. Sweet Home Alabama (2002)
Director: Andy Tennant

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This rom-com coasts on formula and familiar Southern stereotypes, but has a winning performance from Reese Witherspoon, great chemistry between her and the various men in her character’s life (including Fred Ward as her father, Josh Lucas and Patrick Dempsey as her love interests, and Ethan Embry as her closeted gay friend), and eventually treats its Alabama milieu with a respect that doesn’t feel forced or insincere. The romantic comedy has been on a long, accelerating slide since the ‘90s ended, but Sweet Home Alabama is one of the few true classics of the genre this century. —Garrett Martin


96. Serendipity (2001)
Director: Peter Chelsom

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Not exactly a heavy-hitter, Serendipity plays with an idea many of us find very seductive: The notion that there is someone out there who’s perfect for you and fate will see to it that you find each other. This seldom happens in real life, so we love it when it happens in movies. John Cusack and Kate Beckinsale play strangers who are inescapably drawn to each other, but after a brief tryst go back to their own lives—except their own lives just seem to have something incalculably missing. The plot’s beyond predictable, but projecting brooding romantic hero depth even in the total absence of script assistance is John Cusack’s superpower. Somehow that, plus great Valentine-to-New-York settings, plus putting Jeremy Piven to especially helpful use, combined with a core idea that just seems fundamentally resonant to a lot of humans—well, it just works, even if there are no surprises to be found in this thing at all. —Amy Glynn


95. Crazy Rich Asians (2018)
Director: John M. Chu

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Chinese-American professor of economics Rachel Chu (Constance Wu) is Chinese-American, and the adaptation of Kevin Kwan’s best-selling book Crazy Rich Asians starkly makes that point, repeatedly. Rachel’s college best friend Peik Lin (an ebullient Awkwafina) calls her a “banana”: “Yellow on the outside, white on the inside,” and attaches a superlative when she says this. Her mother (Tan Kheng Hua), on the occasion of finding out Rachel will be traveling to Singapore to meet her hunky boyfriend’s family, tells her a somewhat uncomfortable truth: “You are Chinese, you speak Mandarin, but in here,” she says, pointing to Rachel’s heart, “You are American.” It is a bittersweet, but rather perceptive observation, one that finely articulates a compounded sense of otherness Rachel feels throughout the film, particularly once the plot gets rolling and Rachel realizes that her debonair Nick Young (Henry Golding) is the son of an obscenely wealthy Singaporean family who leans heavily on traditional Chinese family values and matriarchy. She is middle class, raised by a single mother and, as everyone has been quick to point out, Chinese-American. If Crazy Rich Asians is not as barbed in its satire about the bourgeoisie as one might want in a cultural landscape where it has become more popular to be vocally anti-capitalist (or at least skeptical of capitalism as a system and ideology), it nonetheless sparkles in its in-jokes about Asianness and Chinese families and the interconnectedness of other Asian people. In the skin of a very competent romantic comedy, it is slickly directed by Chu, whose strength in making champagne on a beer budget lies not in the objects on display in and of themselves, but in the color correcting and cinematography by Vanja Cernjul. However, in its keen and sensitive and moving observations about the uncertainty in being Asian-American, it’s always drifting, and Wu’s incredible ability to convey all those ideas wordlessly is what makes the film more than just about a material China girl. —Kyle Turner


94. Overboard (1987)
Director: Garry Marshall

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In a genre that demands ever more creative obstacles to its protagonist’s ultimate destination, Garry Marshall’s Overboard relies on one that can make modern audiences a bit uncomfortable—rich woman (Goldie Hawn) with amnesia fooled into thinking she’s wife to a guy (Kurt Russell) and mother to his children. There’s a great deal of “positioning” to make this more palatable—Hawn’s pre-amnesia character is so dislikable her actual husband feigns not recognizing her after the accident once he realizes she’s lost her memory, and she stiffs Russell’s handyman after a job well done—but ultimately the plot is powered by the chemistry and comic timing of its leads, not on whether a viewer thinks there’s a consent problem. Hawn and Russell make it work, and that alone is enough to make this version (as opposed to the 2018 film starring Anna Farris) worth a spot on this list. —Michael Burgin


93. Tootsie (1982)
Director: Sydney Pollack

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Can you imagine how audiences and critics might react to Tootsie if it came out in theaters today? Sydney Pollack’s film plays with gender roles and layers its portrait of an actor going full drag with gay panic for giggles. You can just picture this film getting lambasted today for making a joke out of homophobia and for having the gall to ask viewers to sympathize with the plight of an actor who has to dress as a woman to find work. But the reason Pollack’s 1982 classic endures is because of its compassionate heart. This is a kind, empathetic movie that puts its hero, Dustin Hoffman’s cranky perfectionist thespian Michael Dorsey, in the shoes of his female peers to teach him (and us) a lesson, not to make snide jokes at the expense of the opposite sex. The humor is never mean-spirited; the message is rarely pompous, though when it is, that’s meant to be part of the point. Tootsie’s sharp comedy makes it a great piece of entertainment, but it’s the film’s sincere sensitivity that makes it timeless. —Andy Crump


92. To All the Boys I’ve Loved Before (2018)
Director: Susan Johnson

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Adapted from Jenny Han’s YA novel of the same title, TATBILB (as its legion of superfans often refer to it) arrived on the cultural landscape with a bang, suggesting the teen rom-com genre might be on the verge a new golden age. Ultimately, the fluency with which director Susan Johnson, Han, and screenwriter Sofia Alvarez speak “teen rom-com” allows them to take the fizzy conventions of the John Hughes films that Lara Jean loves, mix them all up with the 10 Things I Hate About Yous and the Cluelesses and the She’s All Thats that the outfits and soundtrack and Pacific Northwest setting invoke, and send all their best bits and pieces through a machine that modernizes those elements even as it sweetens them to pure confection (yes, even the conflicts). Lara Jean and Peter get together because of a lie, sure, but their intentions toward each other are never anything but pure, and their reactions when trouble hits, never vicious. This sweetness works because, like Johnson et al., we in the audience know what shape rom-coms have historically taken, and are thus ready and able to have our expectations subverted in the purest of ways. This, of course, sets another bar for the new Golden Age of the Teen Rom-Com, but future rom-rom filmmakers shouldn’t fret—To All the Boys I’ve Loved Before has left you a cheat sheet. All you need to remember is that we don’t need another round of lasciviousness, or selfishness, or petty resentment, or teenage revenge. We just need a wholesome Peter Kavinsky, asking his Lara Jean Covey not to break his heart. —Alexis Gunderson


91. Desk Set (1957)
Director: Walter Lang

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Of the nine movies Katherine Hepburn and Spencer Tracy made together, Desk Set may not be the most well-known, but the 1957 romantic comedy was almost shockingly ahead of its time. Hepburn’s Bunny Watson is the head of the research department at the Federal Broadcasting Network, a career woman in a position of power who’s shown in many instances throughout the movie to be damn good at her job. When Tracy’s Richard Sumner, an efficiency expert, shows up to evaluate how the department would function with a computer (in 1957!), he and Bunny predictably butt heads, but their chemistry is undeniable (aided obviously by the fact that Hepburn and Tracy had a 26-year relationship in real life). It’s hard to believe that a movie about a woman whose work comes first, that stars a 50-year-old actress,actually passes the Bechdel test and prominently features a computer was actually made in 1957, but we’re so glad it was. —Bonnie Stiernberg


90. Boy Meets Girl (2014)
Director: Eric Schaeffer

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A small-town Kentucky teen trying to find the “one” gets caught in a sexually confusing, but totally endearing love triangle in Eric Schaeffer’s Boy Meets Girl. Ricky is a town beauty, known for her outspokenness, wit, fashion sense and being trans. When the equally beautiful Francesca arrives in town for her engagement, she’s drawn to Ricky’s charismatic nature. The connection begins as a simple and effortless friendship, but both girls find their mutual interests and understandings quickly morph into something more. The budding relationship gets complicated when Ricky’s best friend becomes jealous, and Francesca’s fiancé finds out. As Ricky balances falling in love and making her dreams come true, she finds that the “one” thing she’s been looking for is right in front of her. We tend to unconsciously politicize transgender films, but Boy Meets Girl dodges that bullet entirely. The film’s ability to be nothing but a sincere romance with a dash of quirky humor makes it a stand out. From having the “sex talk” with your best friend to your first time with the town’s beautiful newcomer, Boy Meets Girl celebrates the frivolity and fragility of young love and young dreams. At the same time, Boy Meets Girl doesn’t shy away from its main character’s identity, instead using it as a lens to explore just how over-complicated it can all be. In the end, Schaeffer’s film is a touching, sweet and fearless portrayal of women falling in love. —Abbey White


89. Love, Simon (2018)
Director: Greg Berlanti

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Love, Simon is the latest entry in the fairly minuscule collection of movies geared towards young LGBTQ people, but it’s in how main character Simon (Nick Robinson) self-actualizes which seems to establish the film firmly in the present. The ironies of Simon’s very liberal family, accepting friends, etc. are no match for deeply rooted anxiety and a proclivity to want to create some sort of identity online, a version of himself only he and one other, his anonymous pen pal Blue, can know. Love, Simon was not the first queer teen movie (though it was being touted as if it was), and it was not even the first queer film to explore digital identities, but the film is nonetheless of interest because of the way that it uses digital spaces to project who Simon wants to be and and what Simon wants gay desire to look like. Simon, brusquely masc-performing and part of a dream middle class family, can exist as an ostensibly more honest version of himself in the digital realm, while writing to an anonymous person named Blue, whom he found by way of a “confessions”-like blog. Love, Simon’s connection to You’ve Got Mail is crucial because of how it articulates the line between artifice and authenticity: Simon, and Blue for that matter, are no less honest for carving out an identity online in which they feel safe enough to reveal an “authentic” part of themselves. The internet has evolved rapidly since Nora Ephron’s film, but the same rules apply. Love, Simon is one of a few very recent queer films that has its protagonist use the internet to imagine who they could be, or who they think they should be. For Simon and Blue, an email thread can be the queer space they need to explore what “being yourself” really means. —Kyle Turner


88. They Came Together (2014)
Director: David Wain

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They Came Together is director David Wain’s giddily absurd, brilliant dissection of romantic comedy tropes. Wain and co-screenwriter Michael Showalter take the baseline structure of a typical rom-com and intentionally fill it with inane, vague details to expose how so many similar movies pretty much only adhere to a paint-by-numbers formula, hoping to extract some degree of charm out of the “hot but accessible and quirky” casting. Their script requires our hapless but lovable leads (Amy Poehler and Paul Rudd, having a blast as they mug for the cameras) to be attracted to each other after the obligatory introduction in which they despise one another. Their mutual point of magnetism: They both like fiction books. This biting spoof is full of digs like this, from the obnoxious cliché of New York City being a third character in the story—repeated 20-something times—to the way the dialogue points out how each of the best friend characters fit certain strict archetypes. As opposed to Wain and Showalter’s ’80s camp movie parody Wet Hot American Summer, demonstrating the duo’s clear affinity for the films they skewered, one wonders just how much they hate the kinds of cookie-cutter rom-coms they go after, if they’re being mean-spirited or just honest about films of which they’ve obviously seen a lot. —Oktay Ege Kozak


87. Chalti Ka Naam Gaadi (1958)
Director: Satyen Bose

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Given their original format to include all sorts of genres within a three-hour films—romance, comedy, action, drama, tragedy—it isn’t unusual to find both romance and comedy in many Bollywood films. Nevertheless, Chalti Ka Naam Gaadi was one of the first Hindi films to focus on a madcap comedy and romance angle, with the drama and action taking more than a backseat in the meandering plot. In fact, Chalti Ka Naam Gaadi has also been described as Bollywood’s version of a Marx Brothers comedy.

The story involves three brothers Brijmohan, Jagmohan and Manmohan who run an auto repair shop, played by three brothers in real life: Ashok Kumar, Anoop Kumar and Kishore Kumar. After being jilted in love, Brijmohan counsels his younger brothers never to trust women. Enter damsel-in-distress Renu, played by the luminous Madhubala, whose car breaks down one stormy night. Manmohan fixes her car, and the pair fall in love. But problems arise when Renu’s father, unaware of Renu’s interest in Manmohan, is approached by the villainous Raja Hardayal Singh, who wants his brother Prakashchand to marry Renu. Turns out that Singh’s royal coffers are empty, and this is one of his many schemes to acquire wealth. Fortunately, Manmohan and his brothers intervene, and after a bout of boxing, the three brothers are united with their loves. Chalti Ka Naam Gaadi features classic songs that are hummed to this day, slapstick comedy and brilliant chemistry between the lead actors. —Aparita Bhandari


86. The Major and The Minor (1942)
Director: Billy Wilder

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The “male gaze” has a lazy eye! Wilder’s first American movie has a way of landing low, if not last, on a lot of lists—indicating that for whatever reason it’s underwatched and rather misunderstood. A cheeky, subversive comedy that plays with male inability to “see” women, The Major and the Minor stars the inimitable Ginger Rogers as Susan Applegate, a young Iowan fed up with hustling at demeaning jobs in New York City. When she gets to Grand Central to catch a train home, she discovers the fare has gone up and the only way she can get on the train is with a half-price child’s ticket. She “disguises” herself as a tween and Shakespearean mistaken-identity hijinks ensue—especially when she stumbles into the sleeper car of Major Philip Kirby (Ray Miland), who finds himself having to take “Sue-Sue” back with him to the military academy where he works. Thanks to his “bum eye” he somehow manages not to notice Sue-Sue is a grown-ass woman, so he’s a little unnerved by his inappropriate attraction to her. Throw in a hideous domineering fiancée, her no-nonsense scientist younger sister and a couple hundred horny boys in military regalia (and, of course, an excellent dance sequence), and you’ve got a farce with heart, wit and ten times the sophistication of the more critically acknowledged Some Like It Hot. It’s been said before and it holds true here: Ginger Rogers could do everything her male counterparts could. Backward, and wearing high heels. Or in this case, saddle shoes. —Amy Glynn


85. Obvious Child (2014)
Director: Gillian Robespierre

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Above all else, Obvious Child is a compassionate film. That might strike pro-life viewers as odd, even offensive, to say since this romantic comedy-drama features a main character getting ready to have an abortion. But in its modest, clear-eyed way, director and co-writer Gillian Robespierre’s feature debut goes beyond the issue’s moral implications to present a realistic, sensitive portrayal of how one young woman makes her decision to terminate her unwanted pregnancy. That the movie also manages to be funny and incredibly sweet is a small marvel. Obvious Child stars rising comic actress Jenny Slate as Donna, a struggling standup in New York. A few years shy of 30, Donna hasn’t quite gotten the hang of anything yet in her life—not her career and not her relationship. (In fact, as the film opens, she walks off stage from a small Brooklyn club to discover that her boyfriend is leaving her for her friend.) Thrown into depression, Donna alternates between stalking her ex and trying to turn her misery into standup material. But it’s not until she meets a wholesome, handsome guy named Max (Jake Lacy) at the club that she can see a possibility for new love—a vision that’s complicated by the fact that she gets pregnant after their one-night stand. Obvious Child seeks to rethink the typical twenty-something romantic comedy. The setup is almost a parody of the scenario usually visited upon a sad-sack protagonist: Not only does Donna lose her boyfriend, she also discovers her job is ending, leaving her in a state of total limbo. But Robespierre upends those conventions with the serious development at the film’s center. Obvious Child isn’t blind to the fact that abortion is the closing of a door and the ending of a possible life, but it’s grownup enough to assume that adults can watch one woman’s journey toward terminating a pregnancy and recognize the emotional intricacies that go into that decision. Touching on a red-hot issue, Obvious Child is agreeably gentle, and even wise. —Tim Grierson


84. Beginners (2011)
Director: Mike Mills

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Christopher Plummer is absolutely smashing as Hal, a man coming out late in life after the death of his wife, Georgia (Mary Page Keller). With intentions of being not a “theoretical” gay but a “practical” one, he dives headfirst into the queer world available to him by immersing himself in both gay politics and in the affections of a much younger lover. In a later timeline, his son Oliver (Ewan McGregor) grieves his mother’s death while also conducting a playful love affair with a complicated young French actress, Anna (Melanie Laurent). Told in flashbacks from the 1930s up to 2003, Beginners demands total concentration from the viewer. Director Mike Mills’ smart, stylized take on Los Angeles modern style is a treat to behold, and each frame is visually captivating. The film is particularly strong as a narrative of coming to grips with one’s true identity. For Hal, this means coming out as both a gay man and as a bit of a partier; for Oliver, this means finally growing out of an extended adolescence and understanding how to love someone else even when loving is painful. For queer people, many of whom end up experiencing both of these realities, the film will particularly hit home. Beginners deserves to be recognized as a classic of queer cinema. —Nick Mattos


83. Scott Pilgrim vs. The World (2010)
Director:   Edgar Wright  

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In many ways, all of Edgar Wright’s films have been romantic comedies in some fashion. Shaun of the Dead just happens to have zombies and Hot Fuzz just happens to have two males as its romantic leads. In this way, Scott Pilgrim vs. The World is perhaps Wright’s most clear-cut attempt at a rom-com. The story deals in a situation that is all too familiar in the relationship world—that of dealing with your romantic partner’s past romantic baggage. However, to paraphrase Scott Pilgrim’s own words, this emotional baggage (i.e., his girlfriend’s evil ex-boyfriends) is actively trying to kill him every 30 seconds. Just as in a musical, where characters start singing when emotions run too high, Scott Pilgrim dishes out videogame-style duels whenever emotional conflict comes into play. As heightened as Scott Pilgrim may seem at times, its undertones are all too relatable. —Mark Rozeman


82. Priceless (2008)
Director: Pierre Salvadori

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In Priceless (often compared to Breakfast at Tiffany’s), Audrey Tautou plays Irène—the most beautiful, dangerous and unapologetic gold digger in the French Riviera. Her best-laid plans begin to go awry as she develops feelings for a man of average means. Rather than date him, she trains him to become an “opportunist” instead. In true rom-com fashion, a series of ridiculous scenes unfold with an important lesson in how-to-get-what-you-want-from-the-opposite-sex: “Not finishing your sentences—as if it pains you too much to go on,” she firmly advises, “is extremely effective.” Irène has little depth, and the same could be said about the film, but it’s pretty obvious that that’s the point. Tautou is such an authentic, Gucci-wearing, femme fatale that it’s difficult to simply loathe her. She is, as usual, sincere in her delivery—even when she is delivering a sincerely superficial character. She also plays an amazingly convincing drunk, which some of the best actresses of our day (ahem, Kate Winslet, ahem) have been unable to accomplish. —Shannon M. Houston


81. Kissing Jessica Stein (2001)
Director: Charles Herman-Wurmfeld

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The ’90s and ’00s were a renaissance for cinematic portrayals of LGBT+ relationships as producers and studios started to see the real hunger for representations of the joys, sorrows, tension and heat that comes with a fling or a partnership. And an understanding that a crossover audience for them is possible, as its $10 million box office take revealed. One of the best films to come out of this new wave was this heartfelt and sweetly funny film, co-written by its stars Jennifer Westfeldt and Heather Juergensen. It’s a simple tale of two women taking a chance on a relationship while trying to navigate the reactions of friends and family since, until then, they’d only dated men. It’s a perfectly balanced work that doesn’t undercut its message by being a laugh-out-loud romp or by showing the women facing the slings and arrows of homophobia. —Robert Ham


80. The Wedding Singer (1998)
Director: Frank Coraci

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Twenty years removed, Frank Coraci’s vision of the mid-’80s by way of the late-’90s bears the pastel aesthetic and pop culture refuse of a parody of that decade more than a clear memory of what was actually going on, but all the better to ground the then-popular caricature of Adam Sandler in a tender role best suited to his natural baby-man weirdness. What Happy Gilmore and Billy Madison did for Sandler’s “stop looking at me swan” voice, The Wedding Singer did for every other aspect of the comic actor, not only mitigating all that past frat boy dipshittery, but demonstrating that he could be a quiet, lovable leading man—a persona he’d go on to hone with his best films (notably, Punch-Drunk Love and The Meyerowitz Stories). The story of a banquet hall’s in-house crooner, Robbie Hart (Sandler), suffering a broken heart (like his name!) to find his way to the true girl of his dreams (Drew Barrymore, simultaneously endearing and cloying) hits each rom-com beat so squarely it’s nearly impossible to not see where this thing is going, but its heady brew of ultra-nostalgia and surreal poptimism, as well as Sandler’s unforced hilarity, serves the genre beautifully. The movie’s only glaring miscue is the repeated lambasting of Robbie’s bandmate George (Alexis Arquette), who navigates an onslaught of audience booing every time he sings Culture Club’s “Do You really Want to Hurt Me?” Since the movie takes place in 1985, the song’s been a certifiable hit for more than two years. The audience’s revulsion is more of a cheap gag than a cultural reality, a mis-remembered joke from a manufactured history—like much of the ’80s of The Wedding Singer, as dated today as it was in 1998. —Dom Sinacola


79. Bull Durham (1988)
Director: Ron Shelton

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I believe in ridiculous names like Crash Davis and Nuke LaLoosh. I believe in romantic comedies about giving up on a certain phase of your life where characters stand up and deliver cliched “I believe” speeches that, despite being borderline cheesy, somehow ring completely true. And yes, I too believe there should be a Constitutional Amendment banning Astroturf and the designated hitter. I believe in Bull Durham. The most engaging presentation of the minor-league life on film—and a pretty salute to baseball, in general—this first installment in the unofficial Kevin Costner Baseball Trilogy proved that baseball could equal big box office. Costner and Susan Sarandon anchor this film that does its part to engender a love for the game and the people who court it. —Bonnie Stiernberg & Michael Burgin


78. While You Were Sleeping (1995)
Director: Jon Turteltaub

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While You Were Sleeping, a throwback romantic comedy in the screwball mode, is impossible not to like, a standout of the genre that holds up more than two decades after its release. More kind-hearted than My Best Friend’s Wedding and more grounded than Return to Me, the film turns a daffy plot into something touching and compulsively watchable. Much of the film’s appeal can be attributed to Sandra Bullock’s performance as Lucy, a lonely CTA employee who moved to Chicago with her ailing father, put her future on hold and never returned to it once he died. (That character description alone is enough to set this film apart from so many “high-powered lawyer” romantic comedies.) Lucy takes tokens from and pines for well-dressed lawyer Peter Callaghan (Peter Gallagher) before—long story short—he ends up in a coma. His family (comprising a number of delightful character actors) assumes she’s his fiancée, “adopting” her as one of theirs, but of course she falls in love with Peter’s furniture-building, salt-of-the-earth brother Jack (Bill Pullman). Aside from its focus on the El and life as a CTA employee (“I sit in a booth like a veal,” Lucy snaps), the film showcases the frigid-yet-twinkly reality of Chicago at Christmas, from Lucy hauling a tree up to her apartment in Logan Square, to exploring Peter’s swanky pad on Lake Shore Drive, to taking a freezing walk with Jack past the Chicago River, always quick to exploit the slapstick possibilities of Chicago cold. —Maura McAndrew


77. Some Kind of Wonderful (1987)
Director: Howard Deutch

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Undeservedly in the shadow of Pretty In Pink (probably due to lesser star power and an admittedly less-awesome soundtrack), Some Kind of Wonderful is in many ways a more quieter and more nuanced version of Hughes’ constantly reemerging theme of young love clouded by the stratification of class and privilege. Keith (Eric Stoltz) is an earnest working-class kid who wants to be a painter and whose dad is very, very determined that he get a college education. He’s got a crush on this A-list girl named Amanda Jones (Lea Thompson) who “passes” for the country club set but actually comes from the wrong side of the tracks, too. Keith’s tomboyish friend Watts (Mary Stuart Masterson) is in love with Keith, who is awfully blind for someone with a painterly eye. She agrees to help Keith spend his entire college savings on a “perfect” date with Amanda, with surprising results. A lot of Hughes movies are mostly fluff, but most of them have at least one Incredibly Awesome Teen Moment: In this case it’s the actually-pretty-smokin’ scene where Watts reminds Keith that he needs kissing practice and offers herself for the job. —Amy Glynn


76. Dilwale Dulhaniya Le Jayenge (1995)
Director: Aditya Chopra

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Usually referred to simply as DDLJ, this movie is credited to have started Shah Rukh Khan on his path to eventual superstardom. Even today, Bollywood actresses tend to play second fiddle to their male counterparts, so Kajol (who goes by her first name) never quite got the same glory. Nevertheless, it’s fair to say that DDLJ changed the game for Hindi rom-com films. Twenty years on, Bollywood films continue to invoke DDLJ as an epitome of romance, with young actors trying to recreate their own versions of Raj and Simran.

Set partially in London and partially in Punjab, India, DDLJ was one of the first films to specifically target an Indian diasporic audience with a story that stays true to Indian traditions such as respect for your elders, while also advocating young lovers to follow their heart. A win-win situation! Raj and Simran accidentally meet on a train trip across Europe. After a couple of cute confrontations, sparks fly between the two. But Simran’s father has promised her hand to a friend’s son in Punjab. On overhearing his daughter’s love for Raj, he flies in a rage and immediately packs the family bags for a flight to India and a quick wedding. Raj follows Simran with the intent to ask her father for Simran’s hand in marriage. He befriends the prospective groom, and slowly wins over all the family members with his shenanigans. But will he be able to convince Simran’s strict father? A hit soundtrack, lovely visuals of India and abroad, and a leading couple that charmed their way into its audiences, all contribute to DDLJ being included in all sorts of Bollywood lists. —Aparita Bhandari


75. Jeffrey (1995)
Director: Christopher Ashley

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Based on a play of the same name, written by Paul Rudnick, this charming and witty little morsel tracks the efforts of its titular character (Stephen Weber) as he attempts, at the peak of the AIDS crisis, to avoid any and all relationships, sexual or otherwise. But when he finally does find a potential partner in the form of a cute HIV+ gent (Michael T. Weiss), Jeffrey’s flimsily built wall protecting him from the world starts to crumble. While it plays some very serious concerns for laughs, the film doesn’t shy away from the bitter reality of how many people had been taken away from the world due to AIDS. It also serves as a reminder of why seeking connection and affection in the faces of such trials is so important. Plus, as with all of Rudnick’s work, the film is filled with sharp, pithy dialogue, handled ably by a winning cast that includes some delightful supporting work from Sir Patrick Stewart, Nathan Lane and future Mad Men cast member Bryan Batt. —Robert Ham


74. 10 Things I Hate About You (1999)
Director: Gil Junger

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Inspired by William Shakespeare’s The Taming of the Shrew, the 1999 teen comedy places Katherina and Petruchio into modern times as feminist Kat and bad boy Patrick, the breakout roles for Julia Stiles and Heath Ledger. (There are more than a few entries on this list drawn either directly or indirectly from the Bard’s comedies—that guy was a legend!) Patrick is initially paid to charm Kat as a part of an elaborate scheme by Cameron (Joseph Gordon-Levitt) to take out her younger sister, Bianca. Ledger wins Kat and the majority of the female population over during his marching band-accompanied stadium performance of Frankie Valli’s “Can’t Take My Eyes Off You.” Though Kat is angered when finding out about the deal that formed her relationship, the so-called shrew can’t stay mad for too long after receiving a sincere apology and brand new guitar from her Australian beau. With the perfect amount of ‘90s nonsense, the film ends with Letter to Cleo equally perfectly performing Cheap Trick’s “I Want You to Want Me” atop the roof of Padua High School. —Stephanie Sharp


73. Roxanne (1987)
Director: Fred Schepisi

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“Because I was afraid of worms, Roxanne! Worms!” Steve Martin’s late-’80s rom-com isn’t just his take on Edmond Rostand’s play, Cyrano de Bergerac , it’s also a funny depiction of what would happen were everyone to conduct their romantic lives as if they were giant games of Telephone. Roxanne is one of those smart comedies that seems to effortlessly balance complex, often serious themes of romantic attraction, self-esteem, intelligence and the art of conversation with hilarious pratfalls, physical comedy and sight gags. Even iconic film critics Gene Siskel and Roger Ebert agreed on how wonderful this romantic comedy was, commenting on its effervescence and Martin’s ability to take the story of Cyrano de Bergerac and successfully make it his own. Plus, you can’t help but smile whenever Martin’s prosthetic nose shows up on screen. —Anita George


72. How Stella Got Her Groove Back (1998)

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Twenty years after Stella met Winston in Jamaica, and we’re still routinely bombarded with films where 40-year-old men are in relationships with 20-something women, and no one bats an eye. And, of course, the reverse is hardly ever depicted. Stella Payne’s story—that of a successful stockbroker in her 40s who finds a 20-year-old boy toy (turned genuine romantic interest)—would be a wonder to see on screen today. But it was never meant t ok be an especially complicated movie. The premise is simple, the setting is gorgeous and the cast is perfect. You can’t really beat Angela Bassett and Taye Diggs mingling and making love under the sun in Montego Bay. But it’s important to note that the movie also succeeds as a portrait of friendship (and also grief), with Whoopi Goldberg as Stella’s best friend, accomplice and life saver, Delilah. The movie was not without its flaws (including a very Hollywood ending) but, as Hollywood continues to pay itself on the back for all its strides in diversity (completely ignoring issues like colorism and ageism), ask yourself—when’s the last time you saw a dark-skinned woman over 35, falling in love with a dark-skinned man, whilst her dark-skinned girlfriend cheers her on? How Stella Got Her Groove Back is a marvel, and a reminder that, in so many ways, the ’90s were good to us. —Shannon M. Houston


71. Notting Hill (1999)
Director: Roger Michell

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Like most good romantic comedies, everything about Notting Hill is an absolute dream: Oh, you’re a world-famous American actress, wealthy and beloved by millions? Neat. And you’re staying in one of the most beautiful neighborhoods in London (one of the most beautiful cities in the world)? Super cool. But oh no! You collide with a guy in the street, and he spills orange juice all over you! Life is ruined! But wait a second. He’s an adorable independent bookstore owner with a group of quirky friends (including a hilarious Rhys Ifans and a pre-Downton Abbey Hugh Bonneville) and a penchant for spitting out screenwriter Richard Curtis’ (Four Weddings and a Funeral, Love Actually) charming one-liners and the face of Hugh Grant, and this is your meet-cute. Anna (Julia Roberts) may “just be a girl, standing in front of a boy, asking him to love her” … but she’s a damn lucky girl. —Bonnie Stiernberg


70. Lars and the Real Girl (2007)
Director: Craig Gillespie

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Lars and the Real Girl’s premise should have been cringe-worthy: Ryan Gosling dates a life-sized sex doll, and the entire town goes to great lengths to protect the fairy tale. But Nancy Oliver’s Oscar-nominated script is so gentle, and so melancholic, that it becomes a quietly powerful story of a stunted man who finally comes of age. Darkly funny but sweet-natured, Lars is a small treasure. —Jeremy Medina


69. About a Boy (2002)
Directors: Chris Weitz, Paul Weitz

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No stranger to romantic comedies, Hugh Grant delivered perhaps his best performance ever in About a Boy, a different kind of rom-com. Through his relationship with a young teenager, Grant subtly transforms from notorious womanizer into, well, a man capable of loving the beautiful Rachel Weisz. Grant’s relationship with the boy is tender and thoughtful, much like the film itself. —Jeremy Medina


68. Shakespeare in Love (1998)
Director: John Madden

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Shakespeare can be found throughout this list, as modern takes on his comedies abound, but Marc Norman and Tom Stoppard’s Oscar-winning original script puts the historical romance in romantic comedies, serving up a film that provides a rousing look at Elizabethan theater (and the characters who populated it) as it imagines the real inspiration for some of William Shakespeare’s early successes. Joseph Fiennes stars as the Bard and Gwyneth Paltrow as Viola de Lesseps in a film that is a treasure trove of references and mood for lovers of Shakespeare and of theater in general. (Its presentation of Romeo and Juliet is among the best film adaptations of the tragedy, even though it’s just in the background here.) But John Madden’s film is not just for Bardolators—the non-initiated will find the combination of Fiennes and Paltrow (and Geoffrey Rush, Colin Firth, Ben Affleck and Judi Dench) and this tale of star-crossed love both joyous and heart-wrenching. They might also decide this Shakespeare guy is worth checking out. —Michael Burgin


67. But I’m A Cheerleader (1999)
Director: Jamie Babbit

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In our current climate, it feels strange to have a gay conversion therapy camp serve as the backdrop for a love affair between two young women. Especially now that we know the devastating psychological effects that those practices can have on the people sent to be “changed.” But the core message of this late ’90s gem is clear: our LGBT+ brothers and sisters were born this way and they deserve love just as much as we do. Luckily for our heroine Megan (Natasha Lyonne), she finds that love with Graham (Clea DuVall), another kid sent by her parents to be converted to heterosexuality. Their connection and chemistry is immediate, given life by the understated and thoughtful performances by the two leads. —Robert Ham


66. Something Wild (1986)
Director: Jonathan Demme

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Something Wild offers the odd-couple pairing of Charles Driggs (Jeff Daniels), a vice-president of a banking company living a comfortable existence in a Long Island suburb, and Audrey Hankel (Melanie Griffith), a free-spirited woman seemingly without attachments, but also with a lot of money at her disposal to fund her devil-may-care ways. At first introducing herself to Charles as Lulu, Audrey basically ropes this yuppie into following her on a bizarre road trip throughout a good part of the East Coast—an adventure that, true to genre form, encompasses everything from screwball comedy to violent thriller, with the tone often shifting on a dime. Certainly, Demme’s film lives up to its title just in the all-over-the-place story it weaves. But the film is more than just the sum of its deliberately disparate parts—especially because neither of these two characters can be easily pinned down as types. The first time we see Charles in the film, he’s walking away from a diner having not paid for his meal—an act he later justifies as his way of rebelling within the system. Whether that is in fact true or not, it’s nevertheless clear that he does have certain unruly impulses in him just itching to pop out—which naturally catches the eye of someone like Audrey, who has made such unruliness her life’s mantra. But Audrey isn’t simply the kind of character who would later become known as the “Manic Pixie Dream Girl.” Both Audrey and especially Charles do learn new things about themselves during this odyssey—but it’s not as simple as Audrey learning the dangers of her unfettered lifestyle and Charles becoming more of a bad-ass by embracing that same lifestyle. Instead of being about self-improvement, Something Wild is more about self-awareness: a realization of how complex human beings can be. —Kenji Fujishima


65. As Good as It Gets (1997)
Director: James L. Brooks

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Jack Nicholson  is not exactly the first person who comes to mind when you think romantic leading man. Certainly, when we first meet Melvin Udall, the mean-tempered, OCD-afflicted curmudgeon at the center of James L. Brooks’ As Good As It Gets, it’s clear he’s no Tom Hanks. That is, until he is one day forced to take care of his neighbor’s dog. This event serves as the catalyst for a poignant Scrooge-like transformation: More in touch with his feelings, Melvin soon grows close to the single-mother/waitress (Helen Hunt) at his favorite restaurant and, in the end, overcomes his self-centeredness and lets her know how highly he thinks of her. Cheesy? Yes. But damn if it doesn’t work. —Mark Rozeman


64. Splash (1984)
Director:   Ron Howard  

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You know those moments when you unexpectedly discover you have crossed paths with a mermaid and suddenly you start wondering if that near-death experience you thought you had at Cape Cod when you were a kid miiiiiight have been something deeper and weirder? That! One of the first pictures to emanate from Disney’s spankin’ new Touchstone imprint (PG for mildly vulgar language?!) this mild-mannered, warm-hearted comedy, directed by Ron Howard, stars Tom Hanks as a lonely produce wholesaler and Darryl Hannah as the not-so-little Little Mermaid who saves him. From drowning. Literally, followed by figuratively. C’mon guys: metaphor! Aside from being credited with popularizing “Madison” as a name for girls, the film was a box office and critical success for its gosh-darned old-fashioned sweetness and for the great performances by Hanks and Hannah as well as classics from John Candy and Eugene Levy. Ron Howard is a natural at the Wistful School of Comedy and this film is a basically wall-to-wall feel-good. If you’re looking for a rom-com with sharp teeth, keep walkin’-but any fan of Tom Hanks as a rom-com lead needs to see this film. —Amy Glynn


63. Forgetting Sarah Marshall (2008)
Director: Nicholas Stoller

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Following one of the standard romantic comedy tropes, a man (in this case played by Jason Segel) is tempted to chase the wrong girl (Kristen Bell), ignoring the soulmate (Mila Kunis) right in front him. But while we’d seen the set-up before, we’d seen nothing like Segal’s character Peter getting dumped while naked, Russell Brand as the lead singer for Infant Sorrow or Peter’s A Taste For Love Dracula-themed puppet-comedy-rock-opera. Everyone you’d expect (Jonah Hill, Paul Rudd, Kristen Wiig, Bill Hader) co-stars. —Josh Jackson


62. Pretty in Pink (1986)
Director: John Hughes

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Let’s ignore the fact that she ends up with the wrong guy in the end (Team Duckie for life!) and examine what makes Pretty in Pink’s Andie so impossibly cool: She works in a record store and has killer taste in music. Her outfits are daring and incredible. She brushes off insults from evil richie-rich Steff (James Spader) like they ain’t no thang. She supports her deadbeat dad and essentially serves as head of their household. But most importantly, she’s the picture of courage, staying true to herself the whole way through and never changing to please Blane and his wealthy friends—and if there’s any single movie character teen girls should be modeling themselves after as they attempt to swim the treacherous waters of high school (and high school romance) without drowning, she’s the one. —Bonnie Stiernberg


61. Beauty and the Beast
Directors: Gary Trousdale and Kirk Wise

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The first animated film to be nominated for a Best Picture Oscar, Beauty and the Beast, along with The Little Mermaid in 1989 and The Lion King in 1994, composed the last push of classic hand-drawn cartoons before Toy Story tipped the form definitively toward computer animation. As with so many Disney princesses, the role of Beauty (voiced by Paige O’Hara) is to find her prince, but she’s got a little feminist kick to her, constantly burying her nose in a book, dreaming of escaping her provincial life and rejecting the advances of the handsome oaf Gaston (Richard White). When her father, an idiosyncratic inventor whose character design smacks of Albert Einstein, gets lost in the woods and stumbles upon an enchanted castle, its inhabitant—a horrible Beast (Robby Benson)—takes him prisoner. Belle discovers her father’s captivity and offers to take his place. Her arrival is fortuitous, as time is running out to reverse the curse that has rendered Beast so, well, beastly and his staff a raft of household items, including a candelabra named Lumiere (Jerry Orbach), a mantel clock named Cogsworth (David Ogden Stiers), and a teapot named Mrs. Potts (Angela Lansbury). These charmed servants conspire to tame the Beast so that he’ll fall in love with Belle, and she with him, thus breaking the spell that has trapped them in bric-a-brac. The film’s major set pieces are thrilling, especially the Broadway-infused “Be Our Guest” number by Howard Ashman, whose jaunty lyrics seem as familiar today as they did in 1991, and Alan Menken, whose score won an Academy Award. If you like your rom-coms animated and musically inclined, the House of Mouse provides. —Annlee Ellingson


60. Grosse Pointe Blank (1997)
Director: George Armitage

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In the role that probably set the foundation for High Fidelity’s Rob, rom-com mainstay John Cusack plays Martin Q. Blank as a vaguely charismatic, vaguely confident, vaguely organic hitman—the kind of guy one would never suspect is good at killing people for a living. Except: Blank is from the vaguely wealthy Detroit suburb of Grosse Pointe, which means that he’s one of many formless Michigander large adult sons who go on to do things no one has ever expected of them. Before the 2008 Recession, Oakland County, one of Detroit’s surrounding counties, a very popular member of the Metro Detroit family, was among the absolute richest counties in the country. Like Orange County rich. And still no one seems to really remember that—back in even 1997, when the car companies were slaying, no one expected much from a Michigander. Grosse Pointe Blank epitomizes that befuddling state-wide middle child complex in John Cusack’s thoroughly, anxiously casual performance, mapping that angst of arrested development over a wacky love story with old girlfriend Debi (Minnie Driver). —Dom Sinacola


59. Moonstruck (1987)

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“Snap out of it!” A rom-com with a genuinely romantic sensibility (the hopeless kind), Moonstruck is a basically undeniably adorable comedy about chance, family and what it means to “settle.” Pragmatic widow Loretta (Cher) agrees to marry a nice sensible guy (Danny Aiello), but soon finds herself in a sitch with his passionate and mercurial younger brother Ronny (Nicolas Cage). Cher’s comedic chops are not insignificant, and the chemistry between her and Cage is great. The film has an incredible wealth of wonderful supporting performers (perhaps most notably Olympia Dukakis, who plays Cher’s mother). Norman Jewison’s directorial sensibility here might not qualify as “high art” but it’s a damn fine rom-com, with crackling dialogue, tons of energy and seductively likable characters: Apaean to the joys and inevitable sorrows of dealing with your family, this film has spirit and smarts and soul. And a certain image of Cher in opera garb kicking a beer can up a silent Brooklyn street that one could be forgiven for characterizing as “iconic.” —Amy Glynn


58. Bridesmaids (2011)
Director:   Paul Feig  

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Unlike The Hangover, which was basically a long comedy sketch, Bridesmaids is actually a movie. This is always the big question when it comes to comedies. Should you aspire to make a full cinematic experience and risk coming up short (Wedding Crashers) or do you simply shoot for nonstop emotionless laughs and achieve wild success at a less transcendent achievement (Anchorman). Bridesmaids is thoroughly hilarious, complete-narrative cinema thanks to the brilliance of Kristen Wiig. And it has staying power in the typically bro-dominated pantheon of film comedy. —Ryan Carey


57. Breakfast at Tiffany’s (1961)
Director: Blake Edwards

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It can be difficult to overlook the extreme racism of Mickey Rooney playing a Japanese landlord in Blake Edwards’s beloved classic. Nobody should have any problem with people who refuse to watch a movie with such a character in 2018. If you can look past his brief scenes, though, you’ll find a romantic comedy that deserves its iconic reputation. It features Audrey Hepburn at her finest, and is the main reason every Anthropologie is full of books and art prints about her. It’s a romantic comedy that’s both romantic and funny (and, yes, rather racist). —Garrett Martin


56. My Big Fat Greek Wedding (2002)
Director: Joel Zwick

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The little indie rom-com that could, Joel Zwick’s My Big Fat Greek Wedding was the surprise hit of 2002 thanks to a hilarious, loving portrayal of Greek-American culture that hadn’t been seen much on the big screen. Nia Vardalos plays Toula Portokalos, who to the consternation of her family, is engaged to a decidedly non-Greek man. The clash of cultures is at the center of this funny and original film based on Vardalos’ Oscar-nominated screenplay. —Josh Jackson


55. You’ve Got Mail (1998)
Director: Nora Ephron

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Some films are just pure testaments to the power of relatable characters and believable screen chemistry, and Nora Ephron’s You’ve Got Mail is a prime example. Dramatically unsurprising and artistically unremarkable, it still pulls you in with its Jane Austen-esque lover-rival dynamic and general good-naturedness. The third rom-com collaboration between Tom Hanks and Meg Ryan (and Ryan’s most unaffected performance of the trio) is the story of the unlikely (yet inevitable) coupling between an independent bookstore owner and the mogul at the helm of the mega-bookstore that’s threatening to put her out of business. In real life they can’t stand each other—but in an anonymous chat room, they get along and then some. Sailing along on the sheer likability of its protagonists, and the actors who portray them—Ryan’s at her best in a grounded, just-plain-happy performance and Hanks’s kind of limitless plasticity is in full flow—You’ve Got Mail trades in “cute.” If that makes you itch, you’re in for a bit of scratching, but there is a genuine heart to this movie that will reel in even avowed cynics. —Amy Glynn


54. Appropriate Behavior (2014)
Director: Desiree Akhavan

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By default, being a twenty-something is messy—whether it’s dealing with crumbling relationships, jobs you’re too inexperienced for or the lies you tell to appease your parents. Desiree Akhavan explores that universal experience of untangling our identities in 2014’s Appropriate Behavior. Shirin (Akhavan) is a secretly bisexual woman fresh out of a break-up and dedicated to getting ?over her ex-girlfriend. But Shirin’s dispirited attempts to push every aspect of her life back on track fall awkwardly and disappointingly flat at every turn. Shirin can talk her way into a job and a date, but can she keep either? Appropriate Behavior follow one woman’s journey through life telling everyone she’s an adult … until she accidentally becomes one. Rather deftly, Akhavan’s film serves as a commentary on translation—the differences between the language we use, the things we actually mean, and how it all gets twisted. The narrative plays with Shirin’s identities—as an Iranian, a woman, a millennial and a bisexual—sometimes hilariously, other times rather poignantly. All 86 minutes of the film are spent watching Akhavan’s character desperately and unsuccessfully try to say what she wants. But as the responsibilities, one-night stands and brushes with her ex mount, Shirin begins to realize that the real trick to communication is taking the time to understand yourself before trying to communicate that to someone else. Appropriate Behavior is undoubtedly a comedy, but also a heartfelt look at how we learn to say what we mean and be who we are. —Abbey White


53. 13 Going on 30 (2004)
Director: Gary Winick

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What could’ve been easily dismissed as a shameless Big ripoff might be even better than that Tom Hanks classic. Jennifer Garner is at her most charming as a 13-year-old in a grown-up’s body, and perennially underrated Judy Greer shines in her finest film role as Garner’s best frenemy. The gently nostalgic script might deserve the most credit, though—a movie like this could have been ruined by lethal levels of cheese, but 13 Going on 30 has the exact right amount of crowd-pleasing schmaltz. —Allyn Moore


52. The Wedding Banquet (1993)
Director:   Ang Lee  

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The Wedding Banquet, Ang Lee’s foray into a kind of screwball comic style, is his first time examining the lives of gay people. Wai-Tung Gao (Winston Chao) is constantly badgered by his parents to get married, now that he’s in his late 20s, but as dramatic irony would have it, he’s a successful Manhattanite living with his boyfriend, Simon (Mitchell Lichtenstein, son of artist Roy), the two straining to use their quick wits to come up with excuses to stave off Wai-Tung’s marriage. At the behest of Simon, as if to get Wai-Tung’s old-fashioned parents to stop bothering them, he suggests Wai-Tung marry one of his apartment tenants, in turn scoring her, Wei Wei (May Chin), a green card. The couple invite Wai-Tung’s parents to the United States, plan a large wedding and chaos ensues.

In The Wedding Banquet, homosexuality or queerness is enough to transgress tradition. Which sounds obvious but is significant not only because of Wai-Tung’s implied upper middle-class status, but because of the complicated racial dynamics that, too, exist in the film. Wai-Tung’s partnership with a white man is, not unlike the interracial marriage in Ang Lee’s first film, Pushing Hands, easily read as either a move forward into a modern world of modern relationships, or a threat to some idea of racial purity within Asianness (an idea in Crazy Rich Asians). The Taiwanese diaspora at work, folks. —Mark Rozeman


51. Houseboat (1958)
Director: Melville Shavelson

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In a lot of ways, Houseboat is a bit of a trivium, although it’s never unsatisfying to watch Cary Grant or Sophia Loren, like, ever. Grant plays a widowed father who takes his rather bratty and coddled children to live on a busted-up houseboat, ends up with Sophia Loren as his housekeeper and falls in love with her. A big star vehicle with a kind heart, Houseboat won’t strike everyone as cinematic dynamite, especially when there is really one standout feature to this film (significant because it was really unusual for its time). This film is very focused on the emotional world of the children, surprisingly clear-eyed and perspicacious about the mixed feelings kids have when their parents re-partner. Falling in love with Sophia Loren is easy. Winning back the hearts of your disaffected children? That’s tougher—but worth watching if for no other reason than to see Grant take it on with his typical panache. —Amy Glynn


50. Sleepless in Seattle (1993)
Director: Nora Ephron

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Sleepless in Seattle is essentially one giant love letter to 1957’s An Affair to Remember from writer/director Nora Ephron. Rita Wilson gives a memorable teary summary of the movie, and Annie (Meg Ryan) watches it before writing to Sam (Tom Hanks) inviting him to meet her at the top of the Empire State Building—the way Cary Grant and Deborah Kerr attempt to in their movie—on Valentine’s Day. When they finally meet on the observation deck, the theme from An Affair to Remember swells, setting the mood for anyone with an appreciation for good rom-coms. —Bonnie Stiernberg


49. Juno (2007)
Director:   Jason Reitman  

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Much has been made about the Diablo Cody-isms that permeate the script, but the heart of Juno is Ellen Page, and her coming to terms with her feelings for good pal Paulie (Michael Cera). Sure, it takes getting pregnant for her to realize the man of her dreams is the wimp in yellow shorts, but then, the characters in Juno aren’t remembered for their brevity—for getting efficiently from points “A” to “B,” especially when it comes to words—anyway. Page’s heavy-lifting deserved every bit of that Oscar nomination. —Jeremy Medina


48. The Purple Rose of Cairo (1985)
Director:   Woody Allen  

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Woody Allen  has stated a number of times The Purple Rose of Cairo is among his favorite films he’s directed, and it’s no wonder—it’s his most empathetic and imaginative film to date, which is saying a lot for the guy. Delivering her best performance of the 13 films she made with the director, Mia Farrow plays a lonely woman who escapes to the movies to live out her fantasies through her favorite actors. Even when the dashing Tom Baxter (a young Jeff Daniels) steps out of the screen and into her life, she keeps her emotions and expectations in check: “I just met a wonderful new man. He’s fictional, but you can’t have everything.” Purple Rose whimsically builds toward a gut-wrenching, elegiac final shot that reminds us, as dramatic as it may sound, why we go to the movies in the first place. —Jeremy Medina


47. Silver Linings Playbook (2012)
Director: David O. Russell

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With leads as winning as Bradley Cooper and Jennifer Lawrence, aas well as David O. Russell’s signature mix of clever and sincere dialogue, the hook is set. Every single detail doesn’t gel—Chris Tucker’s role as Danny, Pat Jr’s escape-prone friend from the treatment facility, seems a bit extraneous—but it doesn’t need to. By the end of the dance competition finale (yeah, there’s that), the audience, actors and director are on exactly the same page in Russell’s playbook. —Michael Burgin


46. Enchanted (2007)
Director: Kevin Lima

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Disney’s self-referential meta-comedy features a Princess (Giselle, played by Amy Adams) forced out of her 2D animated universe by an evil Queen on the morning of her (you know, literal) fairytale wedding…and into New York City, where she meets the ultimate romantic temptation, a divorce attorney (Patrick Dempsey). Giselle’s Prince tries to find her; Dempsey’s Robert has trouble getting his kid to like Nancy (Idina Menzel), whom he intends to marry; minions from the animated world arrive (nobody minions quite like Timothy Spall); a Shakespearean collision ensues; and then there’s a big ol’ Happily Ever After. Peppered with references to the Disney canon and featuring cameos by a whole bunch of voice actors from previous animated features (including Julie Andrews as the Narrator), the film is less about the romance between Adams and Dempsey than a send-up of the whole concept of fairytales: princes and princesses and happy endings and musical numbers which also parody their more earnest predecessors. Enchanted might be a parody, but it’s definitely not the cynical kind, and anyone who grew up on Disney movies (which is probably most of us) will find its layers of reference and self-send-up wonderfully on point. —Amy Glynn


45. There’s Something About Mary (1998)
Directors: Bobby Farrelly, Peter Farrelly

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...and it’s not just hair gel. Cameron Diaz’s titular character is the object of affection for a wide range of guys, not all of whom are NFL quarterback Brett Favre. Not without reason: She combines a certain Audrey Hepburn winsomeness with a certain Ava Gardner crassness, plus a sensibility that is as ’90 as anything this side of Jennifer Aniston’s haircut in Friends Season 1. Throw in a splash of Ben Stiller cringe-theater, Chris Elliott creepypants-comedy and cameos by both Jonathan Richman and a certain football star, and you have a Farrelly Brothers classic—raunchy, ridiculous, and somehow guffaw-inducing even when you know better. It’s sort of like if Otto Preminger’s masterpiece Laura were set in 1990s Florida and made into a comedy by drunk frat boys. What’s not to love? —Amy Glynn


44. How to Marry a Millionaire (1953)
Director: Jean Negulesco

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Recipe: Equal parts Marilyn Monroe, Betty Grable and Lauren Bacall as three unabashed gold-diggers. Add screwball plot, pioneering CinemaScope wide-screen production, great New York exteriors, then shake vigorously. If director Jean Negulesco stumbled a bit in his early use of the CinemaScope process, How to Marry a Millionaire packs enough star power, writing witty enough to withstand a pretty annoying premise, to potentially make you forget to notice. It might have been a disaster if it hadn’t been cast with such a striking human power chord, remaining 100% worth watching thanks to the pure sparkle and swagger of its three female leads. —Amy Glynn


43. Wall-E (2008)
Director: Andrew Stanton

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Before you cry foul, let’s think about the plot of Wall-E for a second: lonely boy meets girl, falls in love, and chases girl to the ends of the earth—or, in this case, the universe. How is that not a romantic comedy? Nevermind they’re robots. Nevermind the lack of dialogue. Nevermind it’s animated. When Wall-E and Eve dance together in the sky amongst the stars, we might as well be watching the second coming of Fred Astaire and Ginger Rogers. —Jeremy Medina


42. A Room with a View (1985)
Director: James Ivory

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The inclusion of James Ivory, Ismail Merchant and Ruth Prawer Jhabvala’s adaptation of E.M. Forster’s 1908 novel on this list may seem like a stretch at first. Sure, the film has romance to spare—two attractive young people kept initially apart by class; a dramatic, forbidden kiss in a field of barley; “exotic” foreign locales—but once you get past the Edwardian stateliness of it all (and partially in tandem with it), A Room with a View is pretty damn hilarious. A delightful comedy of manners simmers throughout thanks to Maggie Smith’s proto-Downton Dowager (she was a spry 49 or so at the time) and Julian Sands’ amusingly intense and sincere George, but the true scene stealer comes in the form of Daniel Day-Lewis’ coal-to-diamond clenched sphincter of a man, Cecil Vyse. (Try to take your eyes off him.) More than most films on this list, A Room with a View’s humor shines through with repeated viewings. Meanwhile, the trajectory of George and Lucy (Helena Bonham-Carter) ticks off all the steps and stages of the genre, leaving the viewer elated and satiated. (Just don’t look up Forster’s 1958 addendum, “A Room without a View” and its somewhat gloomy prognostication of the young couple’s future.) —Michael Burgin


41. The Prizefighter and the Lady (1933)
Director: W.S. Van Dyke

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The light romantic comedy stylings of this film are livened up by the star appearances of several celebrity prizefighters of the period. Myrna Loy plays a fashionable nightclub singer and gangster’s moll toying with the heart of Max Baer, the real-life heavyweight champion. With the legendary Jack Dempsey as a referee and Baer’s real opponent Primo Carnera in the ring, it’s difficult not to play a game of “spot the celebrity” as you’re watching. In spite of the fact that at one point, Baer attempts to do some singing, this is a thoroughly entertaining, if patchy, old Hollywood movie. —Christina Newland


40. Sing Street (2016)
Director: John Carney

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Sing Street spins art out of history, but you might mistake it for pop sensationalism at first glance. If so, you’re forgiven. In sharp contrast to John Carney’s breakout movie, 2007’s sterling adult musical Once, Sing Street aims to please crowds and overburden tear ducts. There’s a sugary surface buoyancy to the film that helps the darkness clouding beneath its exterior go down more easily. Here, look at the plot synopsis: A teenage boy living in Dublin’s inner city in 1985 moves to a new school, falls in love with a girl, and forms a band for the sole purpose of winning her over. If the period Carney uses as his storytelling backdrop doesn’t make Sing Street an ’80s movie, then the mechanics of its story certainly do. You may walk into the film expecting to be delighted and amused. The film won’t let you down in either regard, but it’ll rob you of your breath, too. —Andy Crump


39. Sleeping with Other People (2016)
Director: Leslye Headland

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Up until its recent revival (thanks Netflix?), the romantic comedy has been crying out for an update. Instead of subverting it, rarely has a film embraced the genre and all its tropes quite like the third film from Leslye Headland does. With little more than 90 minutes of sexual tension building between two friends, Headland has managed to create a direct descendent of the films of Frank Capra, Billy Wilder, Rob Reiner and Nora Ephron—and make it just as uproariously funny as its forebears’ best works. Sleeping With Other People pushes at every boundary without ever feeling unnecessarily tawdry; it’s the Cards Against Humanity version of When Harry Met Sally. (There’s even an “I’ll have what she’s having” moment involving a bottle of tea.) Alison Brie could be our decade’s Meg Ryan, and Sudekis could be our Hanks—but there’s no doubt that Leslye Headland will keep making us laugh for years to come. —Josh Jackson


38. Ninotchka (1939)
Director: Ernst Lubitsch

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Greta Garbo’s emotionless bureaucrat personifies the then-young Soviet machine in Ernst Lubitsch’s pre-war classic—at least until she learns to love both a man (Melvyn Douglas) and the freedom of the West while stationed in Paris. It can be a little surprising to see how early our conception of Russian Communism was fixed in popular culture—the jokes often revolve around Russians who can’t believe the mundane creature comforts of the West, which remained a fixture of Cold War anti-Russian comedy into the early 1990s. Still, Garbo is transfixing in her first comedy, backed by genuine romance in her flirtations with Douglas. —Garrett Martin


37. The Big Sick (2017)
Director: Michael Showalter

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The Big Sick can sometimes be awfully conventional, but among its key assets is its radiant view of its characters. Based on the first year in the relationship of married screenwriters Kumail Nanjiani and Emily V. Gordon, this indie rom-com has a mildly risky structure and some trenchant observations about the culture clashes that go on in immigrant families living in America. But what cuts deepest is just how profoundly lovable these people are. That’s not the same as being cutesy: Rather, The Big Sick is defiantly generous, understanding that people are horribly flawed but also capable of immeasurable graciousness when the situation requires. So even when the film stumbles, these characters hold you up. Nanjiani plays a lightly fictionalized version of his younger self, a struggling Chicago stand-up who is having as much success in his career as he in his dating life. Born into a Pakistani family who moved to the United States when he was a boy, he’s a dutiful son, despite lying about being a practicing Muslim and politely deflecting the attempts of his parents (Anupam Kher, Zenobia Shroff) to set him up in an arranged marriage. That’s when he meets Emily (Zoe Kazan), an American grad student with whom he’s instantly smitten. She swears she doesn’t want a relationship, but soon they fall for one another—even though Kumail knows it can’t work out. If he told his parents about Emily, they’d disown him.

That’s not hyperbole: Kumail’s brother Naveed (Adeel Akhtar) reminds him that other Pakistani-American families they know have turned their back on children who romanced people outside of their culture. Kumail has major misgivings about a way of life that’s far less progressive than the America where he was raised, but he can’t risk losing his parents’ love. Produced by Judd Apatow—who’s made a cottage industry out of mixing frank, R-rated comedy with dramatic, emotional moments—The Big Sick undergoes a tonal shift after Emily discovers that Kumail has kept their relationship a secret from his family. After she breaks up with him, Kumail learns through friends that she’s contracted a mysterious illness that progresses so rapidly that she has to be placed in a medically induced coma. Since her parents live in North Carolina, it falls on Kumail to call them, summoning Beth (Holly Hunter) and Terry (Ray Romano) to Chicago to decide what to do next for her. As directed by Michael Showalter (see also: They Came Together), Kumail’s story is littered with grace notes. It’s a film that’s observant about all the small ways that individuals learn how to make the best of bad situations—whether it’s a stalled comedy career, the pleasant badgering of overbearing parents, or the realization that you may have met the love of your life and blown it. But what’s most radical about The Big Sick is its optimistic insistence that a little niceness can make all the difference. —Tim Grierson


36. Adam’s Rib (1949)
Director: George Cukor

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George Cukor’s Adam’s Rib is a curio of a time when misogyny wasn’t so much a fault as a societal given, which may be why the dynamic between married lawyers Adam Bonner (Spencer Tracy) and Amanda Bonner (Katharine Hepburn, whose character thankfully wasn’t named Eve) feels at once well-balanced and hilariously unreal. A prototypical “war of the sexes” comedy in which each side represents the status quo for his or her respective gender, Adam’s Rib transcends its dumbest Mars-vs-Venus trappings by portraying Tracy’s Bonner as a stuffy turd too caught up in his derision of women to do anything about the fact that a famous musician lothario (David Wayne) is getting mighty close to cuckolding him, were Amanda Bonner a dunce susceptible to shameless advances. She’s not, and not once does Hepburn—perfectly cast—give any impression that she’ll fall for it, being clearly the smartest person in any room and fully aware of what kind of effect her extra-marital flirting has on her wussy husband.

The plot is simple: A woman (Judy Holliday) shoots and injures her cheating husband (Tom Ewell) after catching him in the act, so District Attorney Adam must represent the prosecution (cheating asshole) while Amanda, energized by her husband’s blindness regarding a woman’s helplessness when it comes to adultery, takes up the defense. The trial goes as one might expect, with Hepburn’s charisma holding the attention of every scene, but the real surprise in Cukor’s film comes within its final moments, when the rocky marital fall-out between our leads ends in an almost nihilistic bit wherein Adam reveals he can be just as emotionally manipulative as he expects all women are. Which may be screenwriters Ruth Gordon and Garson Kanin’s funniest joke: Adam’s Rib is about how men and women are equal only in how equally terrible they can be to each other. —Dom Sinacola


35. Coming to America (1988)
Director: John Landis

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If this movie consisted of the barbershop scenes inside of My-T-Sharp and nothing else, it would still be one of the greatest comedies of all time. Eddie Murphy and Arsenio Hall teamed up with director John Landis (Blues Brothers) and created a classic. As Prince Akeem from the fictional African country of Zamunda, Murphy travels to the great United States of America to evade his arranged marriage and find true love (in Queens, obviously). Akeem encounters all of the wonders of black America, but the satirical twist is genius—the black preacher (via Hall as the incomparable Reverend Brown), the club scene, the barbershop, hip-hop culture, and Soul Glo—it’s all here. Cameos from actors like Cuba Gooding Jr., Samuel L. Jackson, Louie Anderson, and Murphy’s Trading Places co-stars Don Ameche and Ralph Bellamy take the Coming to America experience to a whole new level. An excellent comedy and a great tribute to New York City, this story of a prince just looking to be loved is a must-see for everyone—including those of us who’ve already seen it. —Shannon Houston


34. A Matter of Life and Death (1947)
Directors: Michael Powell, Emeric Pressburger

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Michael Powell and Emeric Pressburger (“the Archers”) had a unique ability to take epic subject matter and extract the simple human story out of it. The grand nature of the universe might be unknowable to us, but it’s our ability for love and compassion that makes this conflict-filled, relatively small existence so worthwhile. The powers that get in the way of the brand new romance between a wistful Royal Air Force aviator (David Niven) and a loving American radio operator (Kim Hunter) in the Archer’s sublime supernatural melodrama A Matter of Life and Death are as grand as they get. You see, the aviator was supposed to die after his plane was shot down, but due to a clerical error in the afterlife, he survives and falls in love with the radio operator. When a whimsical official from the other world (Marius Goring) finally comes to Earth to collect him, the aviator challenges the decision, claiming that he can’t leave now that the mistake has resulted in his new romance. The following courtroom drama in Heaven twists the film into a treatise on whether or not it’s the individual or that individual’s cultural/national affiliation that matters when it comes to strength of character. Made directly after World War II, the film poses tough yet necessary questions, and who better than the Archers to deliver them via a thoroughly entertaining and breathtaking package? If you appreciate the quirky depictions of the afterlife in comedies like Defending Your Life and Bill & Ted’s Bogus Journey, you have the Archer’s vision to thank for it. A literal stairway to Heaven, optical effects that bend time and space, groovy matte paintings that look like a black-and-white Led Zeppelin cover: A Matter of Life and Death is an absolute delight. —Oktay Ege Kozak


33. Born Yesterday (1950)
Director: George Cukor

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What happens when you combine George Cuckor’s unerring sense of unspooling revelation, Judy Holliday’s stratospheric intelligence and William Holden’s William Holden-ness? With all due respect to Reese Witherspoon, you get the best not-so-dumb dumb blonde ever. Holliday’s turn as mobster-moll Billie Dawn (a reprise of her Broadway role in the stage version of the film) earned her Best Actress awards from the Academy (she edged out Gloria Swanson for Sunset Boulevard, as well as Bette Davis and Anne Baxter, both nominated for All About Eve) and the First Golden Globe for Best Actress. Mobster (Broderick Crawford) finds the crassness and stupidity of his gal a little embarrassing (look who’s talking) so he hires a journalist (Holden) to tutor her and make her a little more presentable at business dinners. And boy, does it work. With a little education under her belt, Billie Dawn discovers she’s not as dumb as everyone’s always told her she was—in fact she wises up so much she outmaneuvers her crooked and abusive husband. There’s plenty to be said on the script’s social commentary on corruption, or about George Cuckor’s directorial chops, which were generally formidable, but the truth is, you’re likely you have to watch it multiple times in order to notice anything other than Holliday, who was pretty much a neutron bomb in a dress. In real life, Holliday had an IQ in the 170s—but man, she was brilliant at playing dumb. —Amy Glynn


32. She’s Gotta Have It (1986)
Director: Spike Lee 

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Spike Lee  arrived as a fully formed talent with this small-budget, black-and-white debut, which wound up being one of the most important movies in the rise of independent films in the 1980s. Lee brought a voice and verisimilitude to the screen that hadn’t been seen before, with a movie that’s smart, funny and audacious. The central theme—that women can sleep around as much as men, and that they shouldn’t be judged or scorned for it—is still relevant 30 years later. In fact, it’s so relevant Lee adapted the movie into a Netflix series that premiered last year. —Garrett Martin


31. Four Weddings and a Funeral (1994)
Director: Mike Newell

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The first of several Richard Curtis-penned rom-coms starring Hugh Grant, Four Weddings and a Funeral follows our favorite bumbling Englishman as he repeatedly runs into the love of his life at—you guessed it—four weddings and a funeral. While much of the movie is lighthearted and some of it borders on cheesy (see Andie MacDowell’s infamous “Is it still raining? I hadn’t noticed” line in its finale), its graver moments, like Fiona (Kristen Scott Thomas) dealing with unrequited feelings or the titular funeral, remind us that love may be goofy and complicated and wonderful, but finding that one true match is serious business. The Academy agreed, nominating the film for Best Picture in a stacked year that included Forrest Gump, Pulp Fiction and The Shawshank Redemption. —Bonnie Stiernberg


30. Clueless (1995)
Director: Amy Heckerling

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The Beverly Hills reboot of Jane Austen’s classic Emma was a sleeper-smash in 1995—and much more importantly, gave the phrase “As if!” to pop culture. Alicia Silverstone is Cher, a pretty, vain, superficial LA teen who goes on a mission to turn ugly-ducking classmate Tai (Brittany Murphy) into a Superswan, only to find herself eclipsed and adrift. A soft-edged satire of nouveau-riche Angeleno culture and simultaneously of the teen rom-com genre, Clueless is neither the most subtle nor the most hard-hitting film of its era, but it’s surprisingly seductive, in large part thanks to Amy Heckerling’s scrupulously researched script, which captured a dialogue style that both represented and influenced teen-speak of the time. —Amy Glynn


29. Bridget Jones’s Diary (2001)
Director: Sharon Maguire

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Diehards may have been initially miffed at her casting, but Renée Zellweger was crucial to the movie’s success, boundlessly charming as Bridget, the British singleton who falls for Hugh Grant’s Daniel Cleaver and (eventually) Colin Firth’s Mark Darcy. From her appallingly bad public speeches to lip-syncing sad F.M. songs in her pajamas, Zellweger refutes every crusty expectation anyone might have had. —Jeremy Medina


28. Knocked Up (2007)
Director:   Judd Apatow  

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For its many schlubby white-man sins—and its wolf-in-dog’s-clothing conservatism—Judd Apatow’s Knocked Up performs the essential romantic-comedy service of focusing on, in drawn-out detail, the consequences of not taking responsibility for oneself in any relationship. Though Alison (Katherine Heigl), television “journalist” and career-minded modern woman, is mostly just an impetus for a typical 20-something dude (Seth Rogen) to learn that it’s important to read a book sometimes instead of going out and getting drunk—Heigl’s character satisfied, despite all of her ambition, with someone whose only demonstrable sense of action is to read said book instead of going out and getting drunk—the two still have a very surprisingly ample amount of chemistry together. Which may just be that particularly Apatowan aspect of romantic comedies at its epitome—namely, that we’re willing to overlook a lot of bad storytelling if we like the characters despite ourselves. —Dom Sinacola


27. The Goodbye Girl (1977)
Director: Herbert Ross

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1977 gave us not only a post-modern take on the romantic comedy with Woody Allen’s Annie Hall but also this throwback to the “rivals become lovers” subgenre made from a snappy script by the great Neil Simon. Richard Dreyfuss gives one of his career best performances as a blustery wannabe actor who is thrown into an apartment with a single mother (Marsha Mason) and her young daughter (Quinn Cummings). Their love affair seems inevitable, but watching them spar and argue and try to reach some level of understanding is half the fun. —Robert Ham


26. Punch-Drunk Love (2002)
Director:   Paul Thomas Anderson  

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It may be hard to recall, but there was once a time when the world believed in Adam Sandler—and we have P.T. Anderson to thank for such a glimpse of hope. Compared to the scope of There Will Be Blood, or the melancholy of Boogie Nights, or the inexorable fascination at the heart of The Master, or the gut-tickling masochism of Phantom Thread, Punch-Drunk Love—a breath of fresh, Technicolor air after the weight of Magnolia—comes off like something of a lark for Anderson, setting the stage for the kind of incisive comic chops the director would later epitomize with Inherent Vice. But far from a bit of fluff or a reactionary stab at a larger audience, Punch-Drunk Love is what happens when a director with so much untapped potential just sort of throws shit at the wall to see what sticks. A simple love story between a squirmy milquetoast (Sandler) and the woman (Emily Watson) who yanks him from his stark blue shell, the film is part musical, part silent film and all surreal comedy. That this is Sandler’s best role is rarely debated; that this may be Jon Brion’s best soundtrack is something we can talk about later. That the rest of the film, which in any other director’s hands would be a total mess, feels so exquisitely felt is almost…magical. And that? That’s that, Mattress Man. —Dom Sinacola


25. Love & Basketball (2000)
Director: Gina Prince-Bythewood

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It’s a particular triumph when a film succeeds in telling a story about true love that isn’t solely focused on the relationship between a man and a woman. Love & Basketball is a classic romantic comedy (though, with all the drama, you can forget how easily and how hard you laughed throughout), not just because of the electric connection between Monica (Sanaa Lathan) and Quincy (Omar Epps), but also because Monica’s true love for the sport of basketball is given as complicated a narrative as her relationship with Quincy. Writer and director Gina Prince-Bythewood weaves a powerful tale that also functions as a coming-of-age drama for two characters trying desperately to define themselves against the families that have defined them for so long. That Love & Basketball is also an incredibly funny portrait of the highs and lows of young love, with easily one of the greatest scores of all time (“You … made … a fool of me…”) makes it iconic. —Shannon M. Houston


24. The 40-Year-Old Virgin (2005)
Director:   Judd Apatow  

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Judd Apatow  has emerged as a major figurehead in the world of “adult” romantic comedies, due largely to his first directorial effort, The 40-Year-Old Virgin, setting the tone for goofy, improvised, , overlong, hilarious messes of movies, anchored by the easy charm of its principal leads. In this case, Steve Carell and Catherine Keener greet their no-nonsense romance with understated performances, strange given the high-concept premise and general lewdness and all-time great French toast scene. —Jeremy Medina


23. Harold and Maude (1971)
Director: Hal Ashby

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The original Daily Variety review begins, “‘Harold and Maude’ has all the fun and gaiety of a burning orphanage.” History has been kinder. Though it may be dark, Harold and Maude is certainly a romantic comedy: Young Harold (Bud Cort) and 79-year-old Maude (Ruth Gordon) do find love, their courting wickedly funny as Harold finds increasingly more gruesome ways to scare off the suitors sent by his mother. Still, Hal Ashby’s masterpiece is unlike any other film of its ilk, before or after its 1971 release, and Gordon is brilliant as the manic pixie dream septuagenarian. Just don’t go in expecting a happily ever after. —Josh Jackson


22. L.A. Story (1991)
Director: Mick Jackson

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Few would argue that Steve Martin doesn’t receive his due as a comedian. Nonetheless, among his filmography, L.A. Story does not always get the attention shown earlier efforts such as The Jerk or Planes, Trains and Automobiles or the somewhat blander fare that came in the 2000s. Depending on how one looks at it, that’s a shame, or perhaps just an opportunity to discover a hidden gem among Martin’s impressive oeuvre. In the hands of a lesser artist, L.A. Story could have easily just been another hit-or-miss collection of cultural clichés—sustained whimsy is not easy to pull off. Instead, Martin’s writing, Mick Jackson’s direction and a stellar cast present a beguiling love letter to the City of Angels and the people who live there, even as Martin’s Harris K. Telemacher and Victoria Tennant’s British journalist Sara McDowel gradually find a path to each other. (And if you’ve ever wondered how Sarah Jessica Parker became a star, consider this film Exhibit A.) —Michael Burgin


21. The Shop Around the Corner (1940)
Director: Ernst Lubitsch

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If history has taught us anything, it’s that nothing makes for a better rom-com than featuring a couple who has spent the majority of the film actively hating each other finally realize that they are actually soulmates. That’s certainly the case with The Shop Around the Corner, legendary director Ernst Lubitsch’s 1940 comedy about two rival employees at a Budapest gift shop who—unbeknownst to them—have been carrying on a flirty correspondence via mail. This film marked the high point of Jimmy Stewart and Margaret Sullivan’s four collaborations together. What’s more, replace the mail correspondence with an email correspondence and replace Jimmy Stewart with Tom Hanks, our modern-day Jimmy Stewart, and you have the 1998 remake, You’ve Got Mail. —Mark Rozeman


20. Pretty Woman (1990)
Director: Garry Marshall

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Sure, from a feminist perspective, the implication that the only way our favorite hooker with a heart of gold (Julia Roberts) can stop turning tricks and make something of herself is to find a wealthy businessman who needs a fake girlfriend (Richard Gere) is problematic to say the least. And yes, Pretty Woman is formulaic—it’s basically Cinderella with pimps instead of evil stepsisters and Jason Alexander as the Skeptical Best Friend—but the class issues it raises are what make it one for the ages. Vivian is bold, unwilling to pretend to be something she’s not, and when she’s wronged by bougie Rodeo Drive store employees, she makes sure they know it, dropping a memorable “BIG mistake. Big. Huge! I have to go shopping now” on them all while rocking an incredible floppy hat. Roberts turns in a career-making performance, bringing charm (along with that famous cackle) to a role that might’ve played as unsympathetic in different hands. —Bonnie Stiernberg


19. The Apartment (1960)
Director: Billy Wilder

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Filmmaker Billy Wilder had an impressively diverse track record from 1944 to 1960, tackling an Oscar-winning drama about alcoholism (The Lost Weekend), two well-regarded films noir (Double Indemnity, Sunset Boulevard), a war drama (Stalag 17), two light-hearted rom-coms (Sabrina, Seven Year Itch) a gripping murder-mystery (Witness for the Prosecution) and perhaps the funniest American movie of all time (Some Like It Hot). Yet, of all these golden credits, one Wilder’s most beloved and memorable achievements was 1960’s The Apartment. Jack Lemmon plays C.C. Baxter, an ambitious office worker who, desperate to climb the corporate ladder, allows his bosses to use his apartment to carry on discreet affairs with their mistresses. Things get complicated, however, when he discovers that his office crush, quirky elevator operator Fran Kubelik (Shirley MacLaine), is one of his bosses’ mistresses. While it actually gets quite bleak at times, The Apartment strikes a perfect balance between laugh-out-loud comedy and emotionally honest drama. Following the career highlight that was his drag-heavy performance in Some Like It Hot, Lemmon here proves that he can play the low-key, straight man with equal dexterity. Likewise, MacLaine’s charming portrayal as the damaged, yet lovable Kubelik would provide the model for rom-com objects of affection for years to come. —Mark Rozeman


18. Singin’ in the Rain (1952)
Directors: Gene Kelly, Stanley Donen

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Though only modestly successful upon release, Singin’ in the Rain rose in critical esteem to become widely considered the best movie musical of all time. A comedic take on the difficult 1920s transition from silent film to “talkies,” the film stars Gene Kelly as a popular silent film star (and dancer, of course), and Jean Hagen as the vain and irritating costar his studio keeps pairing him with romantically. Perhaps the definitive MGM Technicolor musical, the story is adorable and the singing is terrific, but I’m not sure any of its many, many virtues can top the pure explosive vitality and joy that is Gene Kelly in motion. I defy you to watch this and not feel ridiculously happy. —Amy Glynn


17. Moonrise Kingdom (2012)
Director:   Wes Anderson  

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Wes Anderson’s films can come off as chilly and detached, but Moonrise Kingdom exudes a warmth and innocence generated by the earnest adolescent romance at its core. The year is 1965, and the sleepy New England island of New Penzance is stirred to action when Khaki Scout Sam Shakusky (Jared Gilman) and local resident Suzy Bishop (Kara Hayward) run away together. Sam’s fellow Scouts dislike him, and his foster parents don’t want him back. But Sam is full of surprises: He’s a quite skilled outdoorsman, and when he reunites with the mod girl with whom he’s been exchanging letters for a year, he matter-of-factly hands her a bouquet of wildflowers and begins imparting survival tips. Likewise, Suzy is an unexpected rebel with a volatile streak that upsets the balance among her lawyer parents (Bill Murray and Frances McDormand) and three little brothers. Delightfully, Anderson and co-writer Roman Coppola avoid clichés at every opportunity. The forces that would typically work to tear Sam and Suzy apart instead rally behind them, perhaps infected by the conviction of their love, which never wavers, even in argument: “I love you, but you don’t know what you’re talking about.” Moonrise Kingdom is whimsical and, yes, precious, but only in the very best sense of the word. —Annlee Ellingson


16. City Lights (1931)
Director: Charles Chaplin

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In his later years, Charlie Chaplin was known for bringing pathos into his comedy whenever he had the opportunity. City Lights is the movie where he earns every bit of it. While its structure resembles Chaplin’s usual picaresque format, there’s more of a deliberate purpose as the tramp tries to help a poor, blind flower girl, played adorably by Virginia Cherrill. Harry Myers also deserves a mention for his performance as the millionaire who’s generous when he’s drunk and can’t remember his good deeds when he’s sober. —Jeremy Mathews


15. Sabrina (1954)
Director: Billy Wilder

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While boasted two of the most popular leading men of all time in Humphrey Bogart and William Holden, as well as the brilliant Billy Wilder (The Apartment, Some Like It Hot) as director and Ernest Lehman (Sweet Smell of Success, West Side Story) as one of its writers, it owes virtually every ounce of its justifiable status as a classic to the luminous Audrey Hepburn. Hepburn was already a star, having won an Oscar for her breakout role in 1953’s Roman Holiday and here she shines once again. Often described as a romantic comedy, Sabrina has far more dramatic chops than giggles, and the 25-year-old Hepburn more than holds her own against heavyweights Holden and Bogart, taking the Cinderella archetype to new levels. If you can ignore the May-December aspect of the romantic pairings on offer, I dare you not to fall in love with this winning look at romance. The perfect example of the old axiom: “sometimes what you want is right there in front of you.” —Amy Glynn


14. The Lady Eve (1941)
Director: Preston Sturges

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One of director Preston Sturges’ defining films The Lady Eve centers on a beautiful con woman (Barbara Stanwyck) determined to catch the affections (read: the inheritance) of a naive rich boy (Henry Fonda) just recently arrived from a year-long excursion to the Amazon. In a nice twist from the battle-of-the-sexes formula that characterizes countless entries on this list, The Lady Eve finds the traditional gender roles reversed, with Stanwyck’s Jean Harrington acting as the dominant, sexual aggressor with Henry Fonda’s sweet but clueless Charles Pike serving as the passive object of desire. With enough secret identities and broad farce to rival a William Shakespeare play, The Lady Eve stands as a stone-cold American classic. —Mark Rozeman


13. Bringing Up Baby (1938)
Director: Howard Hawks

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The textbook example of a screwball comedy, Bringing Up Baby finds Cary Grant’s uptight paleontologist Dr. David Huxley struggling to keep his life together when the flirtatious agent of chaos that is Katherine Hepburn’s Susan Vance comes crashing into his regimented quotidian. Add in shenanigans involving a baby leopard, a collapsing brontosaurus skeleton and some deftly executed pre-MPAA sexual innuendos, and you have the bones of a flawlessly executed rom-com, an empirical example for all that was to come. —Mark Rozeman


12. Eternal Sunshine of the Spotless Mind (2004)
Director: Michel Gondry

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Michel Gondry’s debut feature, Human Nature, was a whimsical dud, but his follow-up suggested a mature, disciplined director with his playful side intact. Eternal Sunshine of the Spotless Mind traffics in his signature sleights of hand, which serve two touching and tragic love stories: between red-haired Clementine (Kate Winslet) and a supremely sad Joel (Jim Carrey), and between headstrong Mary (Kirsten Dunst) and a pining Stan (Mark Ruffalo). All of their performances—including Gondry’s—stay in your memory long after the credits have rolled. —Stephen Deusner


11. Trouble in Paradise (1932)
Director: Ernst Lubitsch

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Lubitsch’s masterpiece about class, status and seduction focuses on two thieves who fall in love while masquerading as nobility throughout Europe. Made before the Hays Code, it’s a boldly sensual film, with a sexual charge to much of the dialogue and a frank depiction of romantic mores—in fact, once the code was adopted in 1935, the movie was effectively banned from rerelease until the late ’60s. Herbert Marshall and Miriam Hopkins play refined crooks who try to swindle a wealthy widow played by Kay Francis, with romantic and sexual complications arising from Francis and Marshall’s growing relationship and the presence of Francis’s other suitors. It’s a smart, seductive film, with a gorgeous ambiance and a script that sees through the bluster and artificiality of the social hierarchy. It’s also still funny to this day. —Garrett Martin


10. Groundhog Day (1995)
Director: Harold Ramis

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Bill Murray, director/co-writer Harold Ramis and screenwriter Danny Rubin take a Twilight Zone-esque comedic premise—a self-centered weatherman gets stuck experiencing February 2 again and again—and find unexpected profundity. A more conventional film would have love resolve the chronological predicament, but instead, it falls to TV personality Phil (Murray) to become the best version of himself he can possibly be in order to be with Rita (Andie McDowell). Whether it’s a Hollywood comedy challenging middle-class Americans to shake themselves from their middle-class torpor, or a meditation on our unattainable ideas of perfection, Groundhog Day doesn’t just elicit laughs, but leaves audiences more deeply moved than they ever expected—even inspiring some obsessive fans, including one fellow who calculated, down to the day, the number of decades Murray spent in February 2. —Curt Holman


9. Some Like It Hot (1959)
Director: Billy Wilder

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Is Some Like It Hot one of Marilyn Monroe’s best films, or one of her most antithetical? Sugar Kane is, in a nutshell, the kind of character Marilyn struggled so hard to avoid playing for the bulk of her career: a ditzy blonde, a pure sex symbol, someone who exists in the context of the movie just to tickle the male gaze, whether within the story or without. She’s given nothing to work with, as the bulk of the film’s heavy lifting is accorded to Tony Curtis and Jack Lemmon instead. Watching the film in 2017, you may wonder why Billy Wilder slacked on investing Sugar with any level of empathy, why he wrote the character as a one-dimensional object, a trophy for Lemmon and Curtis to compete over. You may also not wonder at all. Some Like It Hot works, even if Marilyn has little to work with other than her persona and her co-star; it’s funny, it’s quick on its feet, and it sells its central joke—that nobody, save for the audience, can see that Curtis and Lemmon are obviously dudes in drag—perfectly, layering just enough self-awareness of its own ridiculousness to keep the gag from going sour. —Andy Crump


8. His Girl Friday (1940)
Director: Howard Hawks

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Special effects have become so sophisticated that many of us have probably forgotten how much pure amazement you can wreak with a great story and a script that doesn’t let up for one second. This amazing, dizzyingly paced screwball comedy by Howard Hawks stars Cary Grant and Rosalind Russell, and takes us back into two of the decade’s hallmark preoccupations: The “remarriage comedy” and the intrigue and obsessiveness of the newspaper world. The minute Russell’s Lindy Johnson stalks into the newspaper office run by her ex-husband Walter Burns (Grant), you know it’s to tell him she’s getting remarried and leaving journalism to raise a family, and you know that’s not how it’s going to end. No high-suspense mystery here. What puts you on the edge of your seat in this film is how you get there. Hilariously acted and expertly filmed, His Girl Friday derives much of its comedic impact from the incredibly clever and lightning-fast banter of the characters. Don’t even think about checking your phone while you’re watching this. In fact, try to blink as little as possible. —Amy Glynn


7. Amélie (2001)
Director: Jean-Pierre Jeunet

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Delicate and delicious, Amélie is an exceedingly lovable little French trifle. With the face of an angel, the heart of a child and the haircut of a Parisian pixie, Amélie Poulain (Audrey Tautou) sweeps us clean off our feet while Tautou launches herself into the American consciousness as the do-gooding waitress who sends her secret crush photos and riddles, masking her identity in order to make their first encounter—and first kiss—the most romantic moment of her life. Her fantastical adventures—in the name of idealized, even cinematic, coupling—unfold in flights of magical realism, Jean-Pierre Jeunet holding up love itself as both realistically magical and magically realistic. —Nick Marino


6. It Happened One Night (1934)
Director: Frank Capra

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It’s OK to not, frankly, give a damn about Gone with the Wind, because Clark Gable’s portrayal of hard-drinking cynical newsman Peter Warne, a man who finds himself on a road trip with runaway rich girl Ellie Andrew (Claudette Colbert), remains the best role of his career. Likewise, Colbert is an endearing hoot as the impulsive runaway. As is ever the case, the two highly opinionated characters, who can’t stand one another at the beginning of the film, inevitably find their feelings softening as they reach the final stretch of their journey. In 1934, It Happened One Night won the five major Academy Awards (Best Picture, Director, Actor, Actress and Screenplay) though, nearly 80 years and countless copycats later, time has somewhat diluted the film’s originality and humor. Nevertheless, its influence, and its delightfulness, looms large. —Mark Rozeman

5. Roman Holiday (1953)
Director: William Wyler

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Roman Holiday is the gold standard for the American romantic comedy, and quite possibly one of the most charming films ever made. Cary Grant and Elizabeth Taylor both turned down the lead roles, and thank God they did, because it’s hard to imagine William Wyler could have gotten this jewel without the absolutely exquisite Audrey Hepburn (in her debut American role), playing opposite Gregory Peck, whose performance prompted my little sister to write to Peck begging him to take her to Prom. Hepburn plays Ann, a young princess fed up with the strictures of her diplomatic tour escaping her unspecified country’s embassy in Rome to explore the world. Peck is Joe Bradley, ex-pat reporter, who finds her asleep on a bench and takes her home without realizing who she is. Once he does, it’s safe to say that Hijinks Ensue. The third principal character in this film is of course the city of Rome, whose imagistic power could have easily overwhelmed a less charismatic star-crossed odd couple than the princess and the newspaper man. End-to-end gorgeous and lovably funny, Roman Holiday is an exemplar of the difference between sweet and hokey. I’m sure there are critics who would pick at this film for being lightweight (it’s supposed to be), or for Hepburn “over-acting” (it got her the only Oscar of her career), or predictable (it’s a love story?)—however, the pacing, the interlocking moments of poignancy and comedy, and the sheer adorable-bomb factor of Peck and Hepburn would make it tough for even the most hardened cynic to turn it off. —Amy Glynn


4. Annie Hall (1977)
Director:   Woody Allen  

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The sole best picture winner in Woody Allen’s canon, Annie Hall takes its time to depict the many dissonant moments that happen in any relationship, the happy and sad, the bittersweet and the just plain bitter. Fighting over which movie to see, laughing while chasing down lobsters in the kitchen—in the film Allen encapsulates the delicacy of the minutiae of love, balancing highs and lows through both simplicity and narrative daring. Allen isn’t known much today as a man of wit and humor, but in this epochal romantic comedy, he plays a man perfectly matched by Diane Keaton (in her Oscar-winning performance). —Jeremy Medina


3. When Harry Met Sally
Director: Rob Reiner

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Easily the most beloved traditional romantic comedy of its decade, the story of Harry (Billy Crystal), Sally (Meg Ryan) and their 12-year journey to couple-hood boasts a pitch-perfect script by Nora Ephron that feeds and feeds off of the unexpected chemistry between its leads. (And with each new generation of lovers watching the diner scene for the first time, another woman laughs and another man sits silently, wondering what’s so funny.) —Michael Burgin


2. The Princess Bride (1987)
Director: Rob Reiner

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Quite possibly the most perfectly executed transformation of a beloved book to a beloved film in the history of the sport. A family-friendly fable with pitch-perfect performances by the entire cast—from main character to bit player—The Princess Bride is easily the most relentlessly quotable film anywhere this side of Monty Python and their Holy Grail. The Westley-Buttercup dynamic of complete devotion given and earned, no matter the obstacles, is to a large degree the Platonic kernel at the heart of the rom-com itself—who wouldn’t prefer their lover’s devotion that clearly expressed and unshakable, no matter how fantastic it might be? Though regarded warmly enough by critics, its status as comedic fable ensures it is criminally underrated on most lists. Inconceivable? Alas, no. But not on this list. —Michael Burgin


1. The Philadelphia Story (1940)
Director: George Cukor

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Can you believe there was a time when Katharine Hepburn was known in Hollywood as “box office poison”? This adaptation of a Broadway hit was a vehicle to get her career back on track after a series of flops. Her performance as icy heiress Tracy Lord in this “remarriage” comedy is a force of nature. Happily, her no-longer-drunken ex is played by Cary Grant, who is a fabulous foil. Jimmy Stewart and Ruth Hussey round out the cast as reporters in not-so-clever disguise. Pretty much everything about this movie is a pure delight, and the script is a masterpiece. —Amy Glynn

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