The 50 Best Romantic Comedies of All Time

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20. Chasing Amy
Year: 1997
Director: Kevin Smith 
Anyone who has listened to enough hours of Kevin Smith’s podcasts or lengthy Q&A sessions knows that, behind his perpetual potty-mouth and flashes of egomania, Smith is a big softie at heart. After two films that reveled in crass slackerdom lifestyles (Clerks and Mallrats), Smith honed his writing voice for his third feature, Chasing Amy. The film stars Ben Affleck as an amateur comic book artist named Holden whose life is thrown awry when he meets a beautiful and vibrant girl named Alyssa (played by Smith’s then-girlfriend Joey Lauren Adams) and instantly falls in love. The problem? Alyssa is a lesbian. Crushed but still determined to spend time with her, Holden develops a close friendship with Alyssa, eventually telling her how he feels with the kind of speech that anyone who has ever experienced a hurtful bout of unrequited love has tossed around in their minds but never found the words to express.—Mark Rozeman

19. Bridget Jones’s Diary
Year: 2001
Director: Sharon Maguire
Diehards may have been initially miffed at her casting, but Renée Zellweger was crucial to the movie’s success. She’s boundlessly charming as Bridget Jones, gaining 20 pounds to play the British singleton who falls for Hugh Grant and (eventually) Colin Firth. From her appalling bad public speeches to lip-synching to Sad F.M. songs in her pajamas, Zellweger carries the film on her (still slender) shoulders.—Jeremy Medina

18. Knocked Up
Year: 2007
Director: Judd Apatow 
Sure, there’s a graphic scene involving a baby coming out of a womb. Yes, there’s nudity and plenty of expletives. And okay, it is sort of strange how a schlub like Seth Rogen can get a girl like Katherine Heigl. Even so, there’s an inherent sweetness to Knocked Up that make it such a pleasure to watch. Judd Apatow’s treatment of the supporting characters, like Paul Rudd and Leslie Mann, also help catapult the film into one of the genre’s very best.—Jeremy Medina

17. The Shop Around the Corner
Year: 1940
Director: Ernst Lubitsch
If the history of the romantic comedy has taught us anything, it’s that nothing makes for a better rom-com than seeing a couple who has spent the majority of the film actively hating each other 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

16. Love Actually
Year: 2003
Director: Richard Curtis
When it comes to portraying love confessions of all varieties, very few can beat the kind on display in Richard Curtis’ epic romantic comedy Love Actually. In one of the 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

15. Pretty Woman
Year: 1990
Director: Garry Marshall
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. (Additional bonus points for inspiring our favorite Donald Glover tweet ever)—Bonnie Stiernberg

14. Sixteen Candles
Year: 1984
Director: John Hughes
It’s the movie that made Molly Ringwald a star, and rightfully so: as Samantha, the everywoman whose parents forgot her birthday and whose crush doesn’t know she exists, she appeals to the angsty high-schooler yearning to be seen in all of us. Samantha’s undeniably middle-of-the-road—she’s not popular, but she’s not a geek; her home life is messy, but it’s not dysfunctional—and that gives her mass appeal, so much so that her story’s become sort of a modern fairy tale, the American Dream of teen romantic comedies.—Bonnie Stiernberg

13. Harold and Maude
Year: 1971
Director: Hal Ashby
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 the darkest film on this list, Harold and Maude is certainly a romantic comedy. Young Harold (Bud Cort) and 79-year-old Maude (Ruth Gordon) do find love. And it is wickedly funny as Harold finds increasingly more gruesome ways to scare off the suitors sent by his mother. But Hal Ashby’s masterpiece is unlike anything we’ve seen before or since 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

12. Moonrise Kingdom
Year: 2012
Director: Wes Anderson 
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

11. The Apartment
Year: 1960
Director: Billy Wilder
Filmmaker Billy Wilder had perhaps one of the greatest, most diverse track records in film history from 1944 to 1960. In this period, he tackled an Oscar-winning drama about alcoholism (The Lost Weekend), two well-regarded film noirs (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. The film has its genesis in Wilder’s first screening of the 1945 David Lean film Brief Encounter, which centers on a married man and woman contemplating an affair. The director reportedly became intrigued during a scene where the two rendezvous at a friend’s apartment. Ignoring the film’s inherent drama, Wilder wondered what kind of person would knowingly rent out their apartment for extramarital liaisons. Thus, the plot for The Apartment was birthed. 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 certainly not the funniest film on this list—it actually gets quite dark 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 manic pixie dream girls for years to come. —Mark Rozeman

10. Four Weddings and a Funeral
Year: 1994
Director: Mike Newell
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 love or the titular funeral, remind us that love may be goofy and complicated and wonderful, but finding that one true love 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

9. High Fidelity
Year: 2000
Director: Stephen Frears
It’s no coincidence Nick Hornby wrote both About a Boy and High Fidelity, and both movie adaptations show up on this list (let’s ignore Fever Pitch for the time being). Hornby really is tapped into the psyche of the 20th century male. John Cusack plays the every-man type who retraces his past girlfriend history only to find he let the perfect woman slip through his fingers. Funny, insightful and insanely quotable, High Fidelity plays like an ultra-hip Woody Allen movie, which is a very good thing indeed.—Jeremy Medina

8. The Philadelphia Story
Year: 1940
Director: George Cukor
There are so many classic screwball comedies where Cary Grant plays the charming ex-husband who (spoiler alert) wins back his wife (see also: His Girl Friday, My Favorite Wife to name a few), that at this point they almost constitute a subgenre. But The Philadelphia Story remains the best due largely to its dynamite cast. Grant’s completely in his element as the boozy, one-liner machine C.K. Dexter Haven. Jimmy Stewart’s smack dab in the middle of his wheelhouse as sweet everyman Mike Connor, and Katherine Hepburn shines as Tracy, who must decide between the glamourous bad boy or the safe alternative. We all know who she winds up with, but it’s still a blast watching her get there.—Bonnie Stiernberg

7. Say Anything
Year: 1989
Director: Cameron Crowe 
In his directorial debut, Cameron Crowe places one of the all-time charming film courtships within that strangely insular time, mid-transition, between high school and college (or career or family). In Lloyd Dobler, the defining role of John Cusack’s career, Crowe presents an appealing, convincing everyman whose pursuit of a girl (Ione Skye), supposedly out of his league, reveals how foolish such handicapping can be in the first place. Though Crowe would go on to create a number of career-launching roles for women (Renee Zellweger and Kate Hudson should thank him, daily), in Say Anything, Dobler rules.—Michael Burgin

6. Eternal Sunshine of the Spotless Mind
Year: 2004
Director: Michel Gondry
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 Kate Winslet and a supremely sad Jim Carrey, and between headstrong Kirsten Dunst and a pining Mark Ruffalo. All of their performances—including Gondry’s—stay in your memory long after the credits have rolled.—Stephen Deusner

5. Manhattan
Year: 1979
Director: Woody Allen 
Gorgeously shot in black-and-white and set against a backdrop of Gershwin’s “Rhapsody in Blue,” Allen’s ode to the city that never sleeps is a profound meditation on love and loss. Allen, Diane Keaton and Michael Murphy play jaded, self-absorbed adults who over-think and over-analyze every aspect of life. Mariel Hemingway beautifully plays Tracy, the young girl in love with Allen and the only character who is honest about her feelings, the only one with the capacity to love whole-heartedly. The other characters are too delicate, too bruised, and too cynical. When Tracy tells him “you have to have a little faith in people” in the film’s touching final scene, our hearts melt a little—love may be fragile and fleeting, but it’s worth the risk every time. Romantic, witty and bittersweet, Manhattan is impeccably crafted, and stands tallest among Allen’s multitude of towering achievements.—Jeremy Medina

4. The Princess Bride
Year: 1987
Director: Rob Reiner
Quite possibly the most perfectly executed transformation of a beloved book to a beloved film in the history of the sport. A family-friendly “kissing movie” with pitch-perfect performances by the entire cast—from main character to bit player—The Princess Bride is the most relentlessly quotable film anywhere this side of Monty Python and their Holy Grail. Though regarded warmly enough by critics, its status as comedic fable ensures it is criminally underrated on most lists. Inconceivable? Alas, no. But unfair, nonetheless.—Michael Burgin

3. Amélie
Year: 2001
Director: Jean-Pierre Jeunet
A delicate, delicious little French trifle, Amélie is easily the most romantic film on this list. The adorable Audrey Tautou launched herself into the American consciousness as the quirky do-gooder 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. Endlessly imaginative and beautifully photographed, Amélie is a film to be treasured.—Jeremy Medina

2. When Harry Met Sally
Year: 1989
Director: Rob Reiner
Easily the most beloved romantic comedy of the ‘80s, the story of Harry (Billy Crystal), Sally (Meg Ryan) and their 12-year journey to couple-hood boasts a solid 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

1. Annie Hall
Year: 1977
Director: Woody Allen 
Annie Hall is the sole best picture winner in Woody Allen’s canon. The film is also one of the best romantic comedies ever, simply because it takes the time to show all of the moments that happen in a relationship—the wide spectrum of happy and sad, of bittersweet and just plain bitter. From fighting over which movie to see, to laughing while chasing down lobsters in the kitchen, Allen perfectly encapsulates the delicate beauty found in the highs and lows of a relationship. It doesn’t hurt that his wit and humor is perfectly matched by Diane Keaton, in her iconic, Oscar-winning performance. Funny with a perceptively intellectual undercurrent, Annie Hall is an enduring classic.—Jeremy Medina

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