58 Romantic Comedies You Need To See Before You Die

1. It Happened One Night (1934)

Columbia Pictures

Directed by: Frank Capra
Written by: Frank Capra and Harry Cohn

Socialite Ellie Andrew (Claudette Colbert) runs away and ends up crossing paths with handsome reporter Peter Warne (Clark Gable). As Peter gets Ellie’s story, they begin to fall for each other. Because the film predates the enforcement of the production code, it was rather racy for the time, including a scene where Ellie shows off her leg.

2. Bringing Up Baby (1938)

Turner Home Entertainment

Directed by: Howard Hawks
Written by: Dudley Nichols and Hagar Wilde

The first of three romantic comedies starring Cary Grant and Katharine Hepburn on this list, Bringing Up Baby also stars a leopard as the titular Baby. It’s a wickedly funny screwball comedy that showcases the chemistry between its two stars, who stand out even with a distractingly dangerous big cat between them.

3. Holiday (1938)

Columbia Pictures

Directed by: George Cukor
Written by: Donald Ogden Stewart and Sidney Buchman

Like Bringing Up Baby before it and The Philadelphia Story after, Holiday stars the inimitable onscreen duo of Cary Grant and Katharine Hepburn. It’s also a comedy of remarriage, as are the other two, which — by featuring divorced characters — allowed for bawdier jokes in the face of contemporary censorship.

4. The Philadelphia Story (1940)

MGM

Directed by: George Cukor
Written by: Donald Ogden Stewart

Socialite Tracy Lord (Katharine Hepburn) is all set to remarry, but her wedding is thrown off course by the arrival of her ex-husband C.K. Dexter Haven (Cary Grant) and tabloid journalist Mike Connor (Jimmy Stewart). An unequivocal classic, The Philadelphia Story is largely considered the greatest of all romantic comedies.

5. His Girl Friday (1940)

Columbia Pictures

Directed by: Howard Hawks
Written by: Charles Lederer

Yet another comedy of remarriage, His Girl Friday stars Cary Grant as newspaper editor Walter Burns and Rosalind Russell as his ex-wife Hildy Johnson. Hildy is about to marry someone new, but she ends up entangled with Walter. If you don’t know how this ends, you might want to brush up on the “comedy of remarriage” genre.

6. Roman Holiday (1953)

Paramount Pictures

Directed by: William Wyler
Written by: William Wyler

Crown princess Ann (Audrey Hepburn) ditches her handlers on a tour of Rome so she can experience the city herself. She ends up crossing paths with Joe Bradley (Gregory Peck), an American reporter, and the two enjoy a whirlwind romance. While the film is a comedy, it does not — spoiler alert — end well for this unlikely couple.

7. The Apartment (1960)

United Artists

Directed by: Billy Wilder
Written by: Billy Wilder and I.A.L. Diamond

Like so many Billy Wilder films, The Apartment blends comedy and drama, but that’s part of its charm. Office worker Bud Baxter (Jack Lemmon) and elevator operator Fran Kubelik (Shirley MacLaine) are both troubled, often falling for the wrong people. But through mishaps and a suicide attempt — seriously — they find each other.

8. Breakfast at Tiffany’s (1961)

Paramount Pictures

Directed by: Blake Edwards
Written by: George Axelrod

Breakfast at Tiffany’s is an unconventional pick for the genre, but then, Holly Golightly (Audrey Hepburn) is an unconventional heroine. There’s a lot about the film that feels dated now — the horrific Japanese stereotype alone — but Holly’s style is timeless, as is her romance with Paul Varjak (George Peppard).

9. Harold and Maude (1971)

Paramount Pictures

Directed by: Hal Ashby
Written by: Colin Higgins

By romantic comedy standards, Harold and Maude is very dark. Harold (Bud Cort) is a troubled young man obsessed with death, and Maude (Ruth Gordon) is a much older woman. But the love they share, however unconventional, teaches both of them about life, and it’s a beautiful thing to watch.

10. Annie Hall (1977)

United Artists

Directed by: Woody Allen
Written by: Woody Allen and Marshall Brickman

These days it’s hard to talk about Woody Allen without acknowledging his daughter Dylan’s sexual abuse allegations. At the same time, a list of the greatest romantic comedies of all time would feel incomplete without the inclusion of the funny, bittersweet Annie Hall, widely regarded as Allen’s finest cinematic achievement.

11. The Goodbye Girl (1977)

Warner Bros.

Directed by: Herbert Ross
Written by: Neil Simon

Adapted from the Neil Simon play, The Goodbye Girl has oddball neurotic Elliot Garfield (Richard Dreyfuss, in an Oscar-winning role) slowly winning over dancer Paula McFadden (Marsha Mason). The two butt heads as they’re forced to share an apartment along with Paula’s daughter, but as is often the case, hostility turns to love.

12. Sixteen Candles (1984)

Universal Pictures

Directed by: John Hughes
Written by: John Hughes

Sam Baker (Molly Ringwald) is having a crappy 16th birthday, which her entire family has forgotten about. She’s also consumed with feelings for hunky Jake Ryan (Michael Schoeffling). It’s a typical ’80s teen comedy — complete with unfortunate stereotypes and rape references — but the fairy-tale ending is still sweet.

13. Better Off Dead (1985)

Paramount Pictures

Directed by: Savage Steve Holland
Written by: Savage Steve Holland

After getting dumped by his girlfriend Beth (Amanda Wyss), Lane Myer (John Cusack) tries repeatedly to commit suicide, with no success. Luckily, he ends up meeting French foreign exchange student Monique (Diane Franklin), who offers him a better alternative to preemptively ending his life over a breakup.

14. Moonstruck (1987)

MGM

Directed by: Norman Jewison
Written by: John Patrick Shanley

Cher won a Best Actress Academy Award for her role as Loretta Castorini, a woman who is tempted away from her boyfriend Johnny Cammareri (Danny Aiello) by his younger brother Ronny (Nicolas Cage). At the same time, she has to please her very opinionated, very loud Sicilian family.

15. The Princess Bride (1987)

20th Century Fox

Directed by: Rob Reiner
Written by: William Goldman

Yes, it’s a kissing book — or movie, in this case. The Princess Bride is so much more than just a romance or a comedy, but at the center of this fantasy adventure is the undying love between Buttercup (Robin Wright) and her farm boy turned pirate, Westley (Cary Elwes). There are no more romantic words than “As you wish.”

16. Roxanne (1987)

Columbia Pictures

Directed by: Fred Schepisi
Written by: Steve Martin

Roxanne is a modern-day update of Cyrano de Bergerac, which explains Steve Martin’s sizable schnoz. He plays C.D. Bales, who writes beautiful love letters to Roxanne (Daryl Hannah) on her new boyfriend’s behalf. For those who have read Cyrano, this movie ends on a much more upbeat note, thankfully.

17. When Harry Met Sally… (1989)

Columbia Pictures

Directed by: Rob Reiner
Written by: Nora Ephron

The question of whether potential romantic interests can ever just be friends has never been more contentious than in When Harry Met Sally…, in which Billy Crystal charmed as Harry, Meg Ryan faked an orgasm as Sally, and the bar for romantic comedies — thanks to Nora Ephron and Rob Reiner — was set impossibly high.

18. Say Anything… (1989)

20th Century Fox

Directed by: Cameron Crowe
Written by: Cameron Crowe

Underachiever Lloyd Dobler (John Cusack) romances valedictorian Diane Court (Ione Skye), despite her father’s objections. Blasting Peter Gabriel on a boombox outside her house is an obvious step in the right direction — one that countless lovelorn losers have attempted in an homage to Cusack’s classic ’80s character.

19. Pretty Woman (1990)

Touchstone Pictures

Directed by: Garry Marshall
Written by: J. F. Lawton

Edward Lewis (Richard Gere) is a successful businessman. Vivian (Julia Roberts) is a hooker with a heart of gold. As Vivian spends the week with Edward — for a sizable $3,000 — she charms her wealthy benefactor, and the two soon realize they have a bond that surpasses the financial arrangement that got them together.

20. L.A. Story (1991)

TriStar Pictures

Directed by: Mick Jackson
Written by: Steve Martin

TV meteorologist Harris K. Telemacher (Steve Martin) has disappointing relationships with social climber Trudy (Marilu Henner) and ditzy model Sandy (Sarah Jessica Parker). Then he meets British journalist Sara (Victoria Tennant) and — with the help of a friendly (and sentient) freeway traffic sign — he eventually wins her over.

21. Groundhog Day (1993)

Columbia Pictures

Directed by: Harold Ramis
Written by: Danny Rubin and Harold Ramis

Groundhog Day is frequently on lists of the best comedies, and yes, it’s truly hilarious. Bill Murray plays selfish TV meteorologist Phil Connors, forced to repeat the same day over and over again. But beyond that, it’s the story of Phil softening up to producer Rita (Andie MacDowell) and learning to make the right choices.

22. Sleepless in Seattle (1993)

TriStar Pictures

Directed by: Nora Ephron
Written by: Nora Ephron, David S. Ward, and Jeff Arch

There are few on-screen couples as overwhelmingly likable as Sam Baldwin (Tom Hanks) and Annie Reed (Meg Ryan) in Sleepless in Seattle. The warm, funny film ends with a grand homage to An Affair to Remember on the Empire State Building: The moment is so classic it may have unseated its predecessor.

23. Muriel’s Wedding (1994)

Miramax Films

Directed by: P. J. Hogan
Written by: P. J. Hogan

Frumpy, awkward Muriel Heslop (Toni Collette) doesn’t have a lot going for her romantically, which is a pity, as she dreams of getting married. Muriel’s Wedding is as much about female friendship and finding empowerment via ABBA as it is about love, but Muriel’s status as a hopeless romantic earns the film a spot here.

24. Four Weddings and a Funeral (1994)

Gramercy Pictures

Directed by: Mike Newell
Written by: Richard Curtis

The title says it all, doesn’t it? Charles (Hugh Grant) keeps running into Carrie (Andie MacDowell) at major life events, but his attempts at courting her are thwarted by his other romantic entanglements and the fact that he’s awkward and hapless when it comes to love — in other words, he’s a total Hugh Grant type.

25. While You Were Sleeping (1995)

Buena Vista Pictures

Directed by: Jon Turteltaub
Written by: Daniel G. Sullivan and Fredric LeBow

It’s kind of a funny story. Lucy Moderatz (Sandra Bullock) is obsessed with a handsome stranger named Peter (Peter Gallagher). When he ends up in a coma, she pretends to be his girlfriend and inadvertently becomes part of his family, meeting and falling for Peter’s younger brother Jack (Bill Pullman). It’s strange but sweet.

26. Clueless (1995)

Paramount Pictures

Directed by: Amy Heckerling
Written by: Amy Heckerling

Clueless is easily the greatest teen movie of the ’90s, but it’s also a pretty wonderful romance — the film is, after all, based on Jane Austen’s Emma, and no one does romance better than Jane Austen. Spoiled rich girl Cher Horowitz (Alicia Silverstone) unexpectedly finds love with her former stepbrother Josh (Paul Rudd).

27. The American President (1995)

Columbia Pictures

Directed by: Rob Reiner
Written by: Aaron Sorkin

Michael Douglas plays President Andrew Shepherd, who has a high approval rating but no love in his life since his wife died of cancer. That all changes when he meets environmental lobbyist Sydney Ellen Wade (Annette Bening). As for how the leader of the free world dates, it’s predictably complicated — and a pleasure to watch.

28. My Best Friend’s Wedding (1997)

TriStar Pictures

Directed by: P. J. Hogan
Written by: Ronald Bass

My Best Friend’s Wedding is one of those movies where you’re not sure which couple you’re rooting for. Julianne (Julia Roberts) and Michael (Dermot Mulroney) have great chemistry — but Michael is poised to marry Kimmy (Cameron Diaz). While perhaps not romantic in the traditional sense, the conclusion is still lovely.

29. Chasing Amy (1997)

Buena Vista Pictures

Directed by: Kevin Smith
Written by: Kevin Smith

Chasing Amy is not a film without controversy: After all, it involves Alyssa Jones (Joey Lauren Adams), a lesbian, falling for Holden McNeil (Ben Affleck). But try not to hold that against it. As Alyssa struggles with her confusing feelings for a man, Holden tries to hold on to the complicated woman he’s fallen in love with.

30. There’s Something About Mary (1998)

20th Century Fox

Directed by: The Farrelly brothers
Written by: The Farrelly brothers, Ed Decter, and John J. Strauss

Sometimes love is messy, as in the gross-out comedy There’s Something About Mary, which adds a twisted (and bodily fluid-laden) edge to the traditional rom-com. Cameron Diaz stars as Mary, pined after by her high school sweetheart Ted (Ben Stiller) and Pat (Matt Dillon), the private detective Ted hired to track Mary down.

31. You’ve Got Mail (1998)

Warner Bros.

Directed by: Nora Ephron
Written by: Nora Ephron and Delia Ephron

In this modern update of The Shop Around the Corner — itself an adaptation of the play Parfumerie — Joe Fox (Tom Hanks) and Kathleen Kelly (Meg Ryan) fall for each other as email pen pals, despite the fact that they can’t stand each other in real life. With its AOL terminology, it remains a charming late-’90s time capsule.

32. The Wedding Singer (1998)

New Line Cinema

Directed by: Frank Coraci
Written by: Tim Herlihy

Wedding singer Robbie Hart (Adam Sandler) gets left at the altar by his girlfriend Linda (Angela Featherstone). He’s pulled out of his depression by waitress Julia Sullivan (Drew Barrymore), who asks for Robbie’s help in planning her own wedding. The two come to realize they’re more compatible with each other than anyone else.

33. Notting Hill (1999)

Universal Pictures

Directed by: Roger Michell
Written by: Richard Curtis

A-list Hollywood star Anna Scott (Julia Roberts, basically playing herself) falls for Will Thacker (Hugh Grant), the owner of an independent bookstore in Notting Hill. Watching the two connect despite their very different lives is a delight, and Anna’s “I’m just a girl, standing in front of a boy, asking him to love her” line is classic.

34. Never Been Kissed (1999)

20th Century Fox

Directed by: Raja Gosnell
Written by: Abby Kohn and Marc Silverstein

You kind of have to ignore the fact that for much of Never Been Kissed, Josie Geller (Drew Barrymore) is falling for a man who thinks she’s a teenager. But it all works out in the end! Reporter Josie is actually undercover as a high school student, and her romance with teacher Sam Coulson (Michael Vartan) ends up being her story.

35. The Best Man (1999)

Universal Pictures

Directed by: Malcolm D. Lee
Written by: Malcolm D. Lee

On the eve of his best friend Lance’s (Morris Chestnut) wedding, author Harper Stewart (Taye Diggs) is struggling with his feelings for girlfriend Robin (Sanaa Lathan) and mixed reactions to a leaked manuscript of his autobiographical novel. The smash hit sequel, The Best Man Holiday, was released in 2013.

36. 10 Things I Hate About You (1999)

Buena Vista Pictures

Directed by: Gil Junger
Written by: Karen McCullah Lutz and Kirsten Smith

In this high school rom-com update of Shakespeare’s Taming of the Shrew, bad boy Patrick (Heath Ledger) tries to woo Kat (Julia Stiles) so that Cameron (Joseph Gordon-Levitt) can date Kat’s popular younger sister Bianca (Larisa Oleynik). 10 Things I Hate About You is smart, funny, and feminist — unlike the original play.

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