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


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