Vanity Fair's 33 Best Romantic Comedies of All Time
by dan_dassow | created - 15 May 2022 | updated - 15 May 2022 | PublicVanity Fair’s Hollywood team compared their personal top ten lists of romantic comedies to create an ultimate list of their 33 best romantic comedies of all time. Their “ultimate list of best romantic comedies is an eclectic mix, containing everything from black-and-white classics to, well, How to Lose a Guy in 10 Days. And while every single pick may not contain every element commonly associated with the romantic comedy, they all fit the American Film Institute’s broad definition of ‘a genre in which the development of a romance leads to comic situations.’”
Which of these romantic comedies is your favorite?
After voting, please discuss here.
Source: Vanity Fair, May 11, 2022
https://www.vanityfair.com/hollywood/2018/08/best-romantic-comedies-list
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1. The Half of It (I) (2020)
PG-13 | 104 min | Comedy, Drama
When smart but cash-strapped teen Ellie Chu agrees to write a love letter for a jock, she doesn't expect to become his friend - or fall for his crush.
Director: Alice Wu | Stars: Leah Lewis, Daniel Diemer, Alexxis Lemire, Wolfgang Novogratz
Votes: 43,296
2. My Big Fat Greek Wedding (2002)
PG | 95 min | Comedy, Drama, Romance
A young Greek woman falls in love with a non-Greek and struggles to get her family to accept him while she comes to terms with her heritage and cultural identity.
Director: Joel Zwick | Stars: Nia Vardalos, John Corbett, Michael Constantine, Christina Eleusiniotis
Votes: 144,695 | Gross: $241.44M
3. Something's Gotta Give (2003)
PG-13 | 128 min | Comedy, Drama, Romance
A swinger on the cusp of being a senior citizen with a taste for young women falls in love with an accomplished woman closer to his age.
Director: Nancy Meyers | Stars: Jack Nicholson, Diane Keaton, Keanu Reeves, Amanda Peet
Votes: 129,249 | Gross: $124.73M
4. Kissing Jessica Stein (2001)
R | 97 min | Comedy, Drama, Romance
A woman searching for the perfect man instead discovers the perfect woman.
Director: Charles Herman-Wurmfeld | Stars: Jennifer Westfeldt, Heather Juergensen, Tovah Feldshuh, Esther Wurmfeld
Votes: 17,443 | Gross: $7.02M
5. Defending Your Life (1991)
PG | 112 min | Comedy, Drama, Fantasy
In an afterlife way-station resembling a major city, the lives of the recently deceased are examined in a court-like setting.
Director: Albert Brooks | Stars: Albert Brooks, Meryl Streep, Rip Torn, Lee Grant
Votes: 21,321 | Gross: $16.37M
6. How to Lose a Guy in 10 Days (2003)
PG-13 | 116 min | Comedy, Romance
Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days.
Director: Donald Petrie | Stars: Kate Hudson, Matthew McConaughey, Adam Goldberg, Kathryn Hahn
Votes: 270,288 | Gross: $105.81M
7. Some Kind of Wonderful (1987)
PG-13 | 95 min | Drama, Romance
When Keith goes out with Amanda, the girl of his dreams, Amanda's ex-boyfriend plans to get back at Keith. Meanwhile, Keith's best friend, tomboy Watts, realizes she has feelings for Keith.
Director: Howard Deutch | Stars: Eric Stoltz, Mary Stuart Masterson, Lea Thompson, Craig Sheffer
Votes: 34,681 | Gross: $18.55M
8. Annie Hall (1977)
PG | 93 min | Comedy, Romance
Alvy Singer, a divorced Jewish comedian, reflects on his relationship with ex-lover Annie Hall, an aspiring nightclub singer, which ended abruptly just like his previous marriages.
Director: Woody Allen | Stars: Woody Allen, Diane Keaton, Tony Roberts, Carol Kane
Votes: 278,537 | Gross: $39.20M
9. Much Ado About Nothing (1993)
PG-13 | 111 min | Comedy, Drama, Romance
Young lovers, and soon to wed, Hero and Claudio conspire to get verbal sparring partners and confirmed singles, Benedick and Beatrice, to wed as well.
Director: Kenneth Branagh | Stars: Kenneth Branagh, Emma Thompson, Keanu Reeves, Kate Beckinsale
Votes: 52,031 | Gross: $22.55M
10. Amélie (2001)
R | 122 min | Comedy, Romance
Despite being caught in her imaginative world, Amelie, a young waitress, decides to help people find happiness. Her quest to spread joy leads her on a journey where she finds true love.
Director: Jean-Pierre Jeunet | Stars: Audrey Tautou, Mathieu Kassovitz, Rufus, Lorella Cravotta
Votes: 794,579 | Gross: $33.23M
11. The Big Sick (2017)
R | 120 min | Comedy, Drama, Romance
Pakistan-born comedian Kumail Nanjiani and grad student Emily Gardner fall in love but struggle as their cultures clash. When Emily contracts a mysterious illness, Kumail finds himself forced to face her feisty parents, his family's expectations, and his true feelings.
Director: Michael Showalter | Stars: Kumail Nanjiani, Zoe Kazan, Holly Hunter, Ray Romano
Votes: 143,651 | Gross: $42.87M
12. Harold and Maude (1971)
PG | 91 min | Comedy, Drama, Romance
Young, rich, and obsessed with death, Harold finds himself changed forever when he meets lively septuagenarian Maude at a funeral.
Director: Hal Ashby | Stars: Ruth Gordon, Bud Cort, Vivian Pickles, Cyril Cusack
Votes: 81,877
13. The Apartment (1960)
Approved | 125 min | Comedy, Drama, Romance
A Manhattan insurance clerk tries to rise in his company by letting its executives use his apartment for trysts, but complications and a romance of his own ensue.
Director: Billy Wilder | Stars: Jack Lemmon, Shirley MacLaine, Fred MacMurray, Ray Walston
Votes: 196,991 | Gross: $18.60M
14. Four Weddings and a Funeral (1994)
R | 117 min | Comedy, Drama, Romance
Over the course of five social occasions, a committed bachelor must consider the notion that he may have discovered love.
Director: Mike Newell | Stars: Hugh Grant, Andie MacDowell, James Fleet, Simon Callow
Votes: 166,260 | Gross: $52.70M
15. Moonstruck (1987)
PG | 102 min | Comedy, Drama, Romance
Loretta Castorini, a bookkeeper from Brooklyn, New York, finds herself in a difficult situation when she falls for the brother of the man she has agreed to marry.
Director: Norman Jewison | Stars: Cher, Nicolas Cage, Olympia Dukakis, Danny Aiello
Votes: 68,590 | Gross: $80.64M
16. The 40-Year-Old Virgin (2005)
R | 116 min | Comedy, Romance
Goaded by his buddies, a nerdy guy who's never "done the deed" only finds the pressure mounting when he meets a single mother.
Director: Judd Apatow | Stars: Steve Carell, Catherine Keener, Paul Rudd, Romany Malco
Votes: 467,390 | Gross: $109.45M
17. The Shop Around the Corner (1940)
Not Rated | 99 min | Comedy, Drama, Romance
Two employees at a gift shop can barely stand each other, without realizing that they are falling in love through the post as each other's anonymous pen pal.
Director: Ernst Lubitsch | Stars: Margaret Sullavan, James Stewart, Frank Morgan, Joseph Schildkraut
Votes: 38,521 | Gross: $0.20M
18. Down with Love (2003)
PG-13 | 101 min | Comedy, Romance
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.
Director: Peyton Reed | Stars: Ewan McGregor, Renée Zellweger, David Hyde Pierce, Sarah Paulson
Votes: 44,375 | Gross: $20.30M
19. His Girl Friday (1940)
Passed | 92 min | Comedy, Drama, Romance
A newspaper editor uses every trick in the book to keep his ace reporter ex-wife from remarrying.
Director: Howard Hawks | Stars: Cary Grant, Rosalind Russell, Ralph Bellamy, Gene Lockhart
Votes: 63,201 | Gross: $0.30M
20. My Best Friend's Wedding (1997)
PG-13 | 105 min | Comedy, Drama, Romance
When a woman's long-time friend reveals he's engaged, she realizes she loves him herself and sets out to get him, with only days before the wedding.
Director: P.J. Hogan | Stars: Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett
Votes: 155,514 | Gross: $127.12M
21. Sleepless in Seattle (1993)
PG | 105 min | Comedy, Drama, Romance
A recently widowed man's son calls a radio talk-show in an attempt to find his father a partner.
Director: Nora Ephron | Stars: Tom Hanks, Meg Ryan, Ross Malinger, Rita Wilson
Votes: 190,978 | Gross: $126.53M
22. Broadcast News (1987)
R | 133 min | Comedy, Drama, Romance
Take two rival television reporters: one handsome, one talented, both male. Add one producer, female. Mix well, and watch the sparks fly.
Director: James L. Brooks | Stars: William Hurt, Albert Brooks, Holly Hunter, Robert Prosky
Votes: 34,144 | Gross: $51.25M
23. Coming to America (1988)
R | 117 min | Comedy, Romance
An extremely pampered African prince travels to Queens, New York and goes undercover to find a wife that he can respect for her intelligence and strong will.
Director: John Landis | Stars: Eddie Murphy, Paul Bates, Garcelle Beauvais, Feather
Votes: 223,687 | Gross: $128.15M
24. It Happened One Night (1934)
Passed | 105 min | Comedy, Romance
A rogue reporter trailing a runaway heiress for a big story joins her on a bus heading from Florida to New York and they end up stuck with each other when the bus leaves them behind at one of the stops along the way.
Director: Frank Capra | Stars: Clark Gable, Claudette Colbert, Walter Connolly, Roscoe Karns
Votes: 112,344 | Gross: $4.36M
25. Notting Hill (1999)
PG-13 | 124 min | Comedy, Drama, Romance
A set of circumstances makes Anna Scott, a famous actress, fall in love with William Thacker, owner of a bookstore in Notting Hill. But the paparazzi's fascination with her complicates their bond.
Director: Roger Michell | Stars: Hugh Grant, Julia Roberts, Richard McCabe, Rhys Ifans
Votes: 342,519 | Gross: $116.09M
26. Roman Holiday (1953)
Passed | 118 min | Comedy, Romance
A bored and sheltered princess escapes her guardians and falls in love with an American newsman in Rome.
Director: William Wyler | Stars: Gregory Peck, Audrey Hepburn, Eddie Albert, Hartley Power
Votes: 147,736
27. Groundhog Day (1993)
PG | 101 min | Comedy, Drama, Fantasy
A narcissistic, self-centered weatherman finds himself in a time loop on Groundhog Day.
Director: Harold Ramis | Stars: Bill Murray, Andie MacDowell, Chris Elliott, Stephen Tobolowsky
Votes: 685,494 | Gross: $70.91M
28. What's Up, Doc? (1972)
G | 94 min | Comedy, Romance
The accidental mix-up of four identical plaid overnight bags leads to a series of increasingly wild and wacky situations.
Director: Peter Bogdanovich | Stars: Barbra Streisand, Ryan O'Neal, Madeline Kahn, Kenneth Mars
Votes: 27,084 | Gross: $10.47M
29. 10 Things I Hate About You (1999)
PG-13 | 97 min | Comedy, Drama, Romance
A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.
Director: Gil Junger | Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik
Votes: 385,714 | Gross: $38.18M
30. Bridget Jones's Diary (2001)
R | 97 min | Comedy, Drama, Romance
Bridget Jones is determined to improve herself while she looks for love in a year in which she keeps a personal diary.
Director: Sharon Maguire | Stars: Renée Zellweger, Colin Firth, Hugh Grant, Gemma Jones
Votes: 263,947 | Gross: $71.54M
31. Clueless (1995)
PG-13 | 97 min | Comedy, Romance
Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other.
Director: Amy Heckerling | Stars: Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd
Votes: 246,134 | Gross: $56.63M
32. You've Got Mail (1998)
PG | 119 min | Comedy, Drama, Romance
Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet, both blissfully unaware that he's trying to put her out of business.
Director: Nora Ephron | Stars: Tom Hanks, Meg Ryan, Greg Kinnear, Parker Posey
Votes: 229,799 | Gross: $115.82M
33. When Harry Met Sally... (1989)
R | 95 min | Comedy, Drama, Romance
Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.
Director: Rob Reiner | Stars: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby
Votes: 242,901 | Gross: $92.82M
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