Favorite Romantic Comedy Movies

by donaldsgordon | created - 17 Dec 2020 | updated - 07 Apr 2023 | Public
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1. Messengers (1999)

118 min | Action, Drama, Romance

Naomi Shimizu is a young career woman working for Enrico Dandolo, an Italian fashion house. That is until one day the company declares bankruptcy. Accustomed to living in luxury she tries ... See full summary »

Director: Yasuo Baba | Stars: Naoko Iijima, Tsuyoshi Kusanagi, Hiroyuki Yabe, Kotomi Kyôno

Votes: 257

2. Dan in Real Life (I) (2007)

PG-13 | 98 min | Comedy, Drama, Romance

65 Metascore

A widower finds out the woman he fell in love with is his brother's girlfriend.

Director: Peter Hedges | Stars: Steve Carell, Juliette Binoche, Dane Cook, Alison Pill

Votes: 107,031 | Gross: $47.64M

3. The Proposal (I) (2009)

PG-13 | 108 min | Comedy, Drama, Romance

48 Metascore

A pushy boss forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation to Canada.

Director: Anne Fletcher | Stars: Sandra Bullock, Ryan Reynolds, Mary Steenburgen, Craig T. Nelson

Votes: 360,662 | Gross: $163.96M

4. Intolerable Cruelty (2003)

PG-13 | 100 min | Comedy, Crime, Romance

71 Metascore

Miles, a high-profile divorce lawyer, wins a case for his rich but adulterous client Rex Rexroth. But Rex's ex-wife, Marylin, who is no saint and is a gold-digger, plots to take revenge on Miles.

Directors: Joel Coen, Ethan Coen | Stars: George Clooney, Catherine Zeta-Jones, Billy Bob Thornton, Geoffrey Rush

Votes: 101,875 | Gross: $35.33M

5. Some Like It Hot (1959)

Passed | 121 min | Comedy, Music, Romance

98 Metascore

After two male musicians witness a mob hit, they flee the state in an all-female band disguised as women, but further complications set in.

Director: Billy Wilder | Stars: Marilyn Monroe, Tony Curtis, Jack Lemmon, George Raft

Votes: 283,700 | Gross: $25.00M

6. Groundhog Day (1993)

PG | 101 min | Comedy, Drama, Fantasy

72 Metascore

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: 685,502 | Gross: $70.91M

7. Silver Linings Playbook (2012)

R | 122 min | Comedy, Drama, Romance

81 Metascore

After a stint in a mental institution, former teacher Pat Solitano moves back in with his parents and tries to reconcile with his ex-wife. Things get more challenging when Pat meets Tiffany, a mysterious girl with problems of her own.

Director: David O. Russell | Stars: Bradley Cooper, Jennifer Lawrence, Robert De Niro, Jacki Weaver

Votes: 743,085 | Gross: $132.09M

8. Jerry Maguire (1996)

R | 139 min | Comedy, Drama, Romance

77 Metascore

When a sports agent has a moral epiphany and is fired for expressing it, he decides to put his new philosophy to the test as an independent agent with the only athlete who stays with him and his former colleague.

Director: Cameron Crowe | Stars: Tom Cruise, Cuba Gooding Jr., Renée Zellweger, Kelly Preston

Votes: 287,186 | Gross: $153.95M

9. The Seven Year Itch (1955)

Not Rated | 105 min | Comedy, Romance

When his family goes away for the summer, a hitherto faithful husband with an overactive imagination is tempted by a beautiful neighbor.

Director: Billy Wilder | Stars: Marilyn Monroe, Tom Ewell, Evelyn Keyes, Sonny Tufts

Votes: 42,502 | Gross: $12.00M

10. Life Is Beautiful (1997)

PG-13 | 116 min | Comedy, Drama, Romance

58 Metascore

When an open-minded Jewish waiter and his son become victims of the Holocaust, he uses a perfect mixture of will, humor and imagination to protect his son from the dangers around their camp.

Director: Roberto Benigni | Stars: Roberto Benigni, Nicoletta Braschi, Giorgio Cantarini, Giustino Durano

Votes: 743,679 | Gross: $57.60M

11. The Apartment (1960)

Approved | 125 min | Comedy, Drama, Romance

94 Metascore

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: 196,990 | Gross: $18.60M

12. It Happened One Night (1934)

Passed | 105 min | Comedy, Romance

87 Metascore

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: 112,345 | Gross: $4.36M

13. Annie Hall (1977)

PG | 93 min | Comedy, Romance

92 Metascore

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: 278,539 | Gross: $39.20M

14. About Time (I) (2013)

R | 123 min | Comedy, Drama, Fantasy

55 Metascore

At the age of 21, Tim discovers he can travel in time and change what happens and has happened in his own life. His decision to make his world a better place by getting a girlfriend turns out not to be as easy as you might think.

Director: Richard Curtis | Stars: Domhnall Gleeson, Rachel McAdams, Bill Nighy, Lydia Wilson

Votes: 386,190 | Gross: $15.32M

15. When Harry Met Sally... (1989)

R | 95 min | Comedy, Drama, Romance

76 Metascore

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: 242,907 | Gross: $92.82M

16. The Terminal (2004)

PG-13 | 128 min | Comedy, Drama, Romance

55 Metascore

An Eastern European tourist unexpectedly finds himself stranded in JFK airport, and must take up temporary residence there.

Director: Steven Spielberg | Stars: Tom Hanks, Catherine Zeta-Jones, Chi McBride, Stanley Tucci

Votes: 495,534 | Gross: $77.87M

17. Johnny Stecchino (1991)

R | 102 min | Comedy, Crime, Romance

A kindhearted but bumbling idiot who likes to steal bananas, is passed off for a snitch hiding from the mob.

Director: Roberto Benigni | Stars: Roberto Benigni, Nicoletta Braschi, Paolo Bonacelli, Franco Volpi

Votes: 11,560 | Gross: $0.57M

18. The 40-Year-Old Virgin (2005)

R | 116 min | Comedy, Romance

73 Metascore

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: 467,394 | Gross: $109.45M

19. Shakespeare in Love (1998)

R | 123 min | Comedy, Drama, History

87 Metascore

The world's greatest ever playwright, William Shakespeare, is young, out of ideas and short of cash, but meets his ideal woman and is inspired to write one of his most famous plays.

Director: John Madden | Stars: Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush, Tom Wilkinson

Votes: 234,433 | Gross: $100.32M

20. Definitely, Maybe (2008)

PG-13 | 112 min | Comedy, Drama, Romance

59 Metascore

A political consultant tries to explain his impending divorce and past relationships to his 11-year-old daughter.

Director: Adam Brooks | Stars: Ryan Reynolds, Rachel Weisz, Abigail Breslin, An Nguyen

Votes: 173,315 | Gross: $31.97M

21. Love, Rosie (2014)

R | 102 min | Comedy, Romance

44 Metascore

Rosie and Alex have been best friends since they were 5, so they couldn't possibly be right for one another...or could they? When it comes to love, life and making the right choices, these two are their own worst enemies.

Director: Christian Ditter | Stars: Lily Collins, Sam Claflin, Christian Cooke, Jaime Winstone

Votes: 155,688 | Gross: $0.02M

22. Easy A (2010)

PG-13 | 92 min | Comedy, Drama, Romance

72 Metascore

When Olive lies to her best friend about losing her virginity to one of the college boys, a girl overhears their conversation. Soon, her story spreads across the entire school like wildfire.

Director: Will Gluck | Stars: Emma Stone, Amanda Bynes, Penn Badgley, Dan Byrd

Votes: 418,259 | Gross: $58.40M

23. To All the Boys I've Loved Before (2018)

TV-14 | 99 min | Comedy, Drama, Romance

64 Metascore

A teenage girl's secret love letters are exposed and wreak havoc on her love life.

Director: Susan Johnson | Stars: Lana Condor, Noah Centineo, Janel Parrish, Anna Cathcart

Votes: 123,946

24. The Sure Thing (1985)

PG-13 | 95 min | Comedy, Drama, Romance

76 Metascore

Walter Gibson is a university freshman going through a dry spell. His old buddy arranges a "sure thing" for him in California. Gibson and his classmate Allison then take a long road trip out to Cali, and both foil each other's plans.

Director: Rob Reiner | Stars: John Cusack, Daphne Zuniga, Anthony Edwards, Boyd Gaines

Votes: 22,193 | Gross: $18.14M

25. The Wedding Singer (1998)

PG-13 | 97 min | Comedy, Music, Romance

60 Metascore

Robbie, a singer, and Julia, a waitress, are both engaged, but to the wrong people. Fortune intervenes to help them discover each other.

Director: Frank Coraci | Stars: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert

Votes: 162,405 | Gross: $80.25M

26. 50 First Dates (2004)

PG-13 | 99 min | Comedy, Drama, Romance

48 Metascore

Henry Roth is a man afraid of commitment until he meets the beautiful Lucy. They hit it off and Henry think he's finally found the girl of his dreams until discovering she has short-term memory loss and forgets him the next day.

Director: Peter Segal | Stars: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin

Votes: 382,474 | Gross: $120.91M

27. Man Up (I) (2015)

R | 88 min | Comedy, Drama, Romance

69 Metascore

A single woman takes the place of a stranger's blind date and finds the perfect man for her.

Director: Ben Palmer | Stars: Lake Bell, Rory Kinnear, Ken Stott, Harriet Walter

Votes: 56,496

28. The Matchmaker (1958)

Approved | 103 min | Romance, Comedy

Thornton Wilder's tale of a matchmaker who desires the man she's supposed to be pairing with another woman.

Director: Joseph Anthony | Stars: Shirley Booth, Anthony Perkins, Shirley MacLaine, Paul Ford

Votes: 1,211

29. Phffft (1954)

Approved | 88 min | Comedy, Romance

While pursing new companions, a former married couple keep running into each other all over town.

Director: Mark Robson | Stars: Judy Holliday, Jack Lemmon, Jack Carson, Kim Novak

Votes: 2,001

30. Friends with Benefits (2011)

R | 109 min | Comedy, Romance

63 Metascore

A young man and woman decide to take their friendship to the next level without becoming a couple, but soon discover that adding sex only leads to complications.

Director: Will Gluck | Stars: Mila Kunis, Justin Timberlake, Patricia Clarkson, Jenna Elfman

Votes: 394,819 | Gross: $55.80M

31. Down with Love (2003)

PG-13 | 101 min | Comedy, Romance

52 Metascore

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: 44,376 | Gross: $20.30M

32. 10 (1979)

R | 122 min | Comedy, Romance

68 Metascore

A Hollywood composer goes through a mid-life crisis and becomes infatuated with a sexy, newly married woman.

Director: Blake Edwards | Stars: Dudley Moore, Bo Derek, Julie Andrews, Robert Webber

Votes: 19,288 | Gross: $74.87M

33. The Kissing Booth (2018)

TV-14 | 105 min | Comedy, Romance

A high school student is forced to confront her secret crush at a kissing booth.

Director: Vince Marcello | Stars: Joey King, Jacob Elordi, Joel Courtney, Megan du Plessis

Votes: 93,572

34. Amélie (2001)

R | 122 min | Comedy, Romance

70 Metascore

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: 794,585 | Gross: $33.23M

35. The Shop Around the Corner (1940)

Not Rated | 99 min | Comedy, Drama, Romance

96 Metascore

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: 38,522 | Gross: $0.20M

36. Charade (1963)

Passed | 113 min | Comedy, Mystery, Romance

83 Metascore

Romance and suspense ensue in Paris as a woman is pursued by several men who want a fortune her murdered husband had stolen. Whom can she trust?

Director: Stanley Donen | Stars: Cary Grant, Audrey Hepburn, Walter Matthau, James Coburn

Votes: 85,627 | Gross: $13.47M

37. 500 Days of Summer (2009)

PG-13 | 95 min | Comedy, Drama, Romance

76 Metascore

After being dumped by the girl he believes to be his soulmate, hopeless romantic Tom Hansen reflects on their relationship to try and figure out where things went wrong and how he can win her back.

Director: Marc Webb | Stars: Zooey Deschanel, Joseph Gordon-Levitt, Geoffrey Arend, Chloë Grace Moretz

Votes: 558,436 | Gross: $32.39M

38. Shall We Dance? (1996)

PG | 136 min | Comedy, Drama, Music

66 Metascore

A successful but unhappy Japanese accountant finds the missing passion in his life when he begins to secretly take ballroom dance lessons.

Director: Masayuki Suô | Stars: Koji Yakusho, Tamiyo Kusakari, Naoto Takenaka, Eri Watanabe

Votes: 11,741 | Gross: $9.68M

39. Love Actually (2003)

R | 135 min | Comedy, Drama, Romance

55 Metascore

Follows the lives of eight very different couples in dealing with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London, England.

Director: Richard Curtis | Stars: Hugh Grant, Martine McCutcheon, Liam Neeson, Laura Linney

Votes: 531,728 | Gross: $59.70M

40. Scott Pilgrim vs. the World (2010)

PG-13 | 112 min | Action, Comedy, Fantasy

69 Metascore

In a magically realistic version of Toronto, a young man must defeat his new girlfriend's seven evil exes one by one in order to win her heart.

Director: Edgar Wright | Stars: Michael Cera, Mary Elizabeth Winstead, Kieran Culkin, Anna Kendrick

Votes: 465,609 | Gross: $31.49M

41. A Scene at the Sea (1991)

101 min | Comedy, Drama, Romance

The lives of a young, hearing-impaired and gloomy couple are fulfilled after the boy holds interest in surfboarding.

Director: Takeshi Kitano | Stars: Claude Maki, Hiroko Ôshima, Sabu Kawahara, Toshizo Fujiwara

Votes: 6,690

42. High Fidelity (2000)

R | 113 min | Comedy, Drama, Music

79 Metascore

Rob, a record store owner and compulsive list maker, recounts his top five breakups, including the one in progress.

Director: Stephen Frears | Stars: John Cusack, Iben Hjejle, Todd Louiso, Jack Black

Votes: 189,845 | Gross: $27.29M

43. Crazy, Stupid, Love. (2011)

PG-13 | 118 min | Comedy, Drama, Romance

68 Metascore

A middle-aged husband's life changes dramatically when his wife asks him for a divorce. He seeks to rediscover his manhood with the help of a newfound friend, Jacob, learning to pick up girls at bars.

Directors: Glenn Ficarra, John Requa | Stars: Steve Carell, Ryan Gosling, Julianne Moore, Emma Stone

Votes: 564,846 | Gross: $84.35M

44. Up in the Air (I) (2009)

R | 109 min | Comedy, Drama, Romance

83 Metascore

Ryan's job is to travel around the country firing off people. When his boss hires Natalie, who proposes firing people via video conference, he tries to convince her that her method is a mistake.

Director: Jason Reitman | Stars: George Clooney, Vera Farmiga, Anna Kendrick, Jason Bateman

Votes: 349,480 | Gross: $83.82M

45. Garden State (2004)

R | 102 min | Comedy, Drama, Romance

67 Metascore

A quietly troubled young man returns home for his mother's funeral after being estranged from his family for a decade.

Director: Zach Braff | Stars: Zach Braff, Peter Sarsgaard, Natalie Portman, Ian Holm

Votes: 223,241 | Gross: $26.78M

46. Irma la Douce (1963)

Approved | 147 min | Comedy, Romance

63 Metascore

When a policeman falls in love with a prostitute, he doesn't want her to see other men, so he creates an alter-ego who will be her only customer.

Director: Billy Wilder | Stars: Jack Lemmon, Shirley MacLaine, Lou Jacobi, Bruce Yarnell

Votes: 21,427 | Gross: $25.25M

47. Pillow Talk (1959)

Passed | 102 min | Comedy, Romance

73 Metascore

An interior decorator and a playboy songwriter share a telephone party line and size each other up.

Director: Michael Gordon | Stars: Rock Hudson, Doris Day, Tony Randall, Thelma Ritter

Votes: 19,189 | Gross: $18.75M

48. There's Something About Mary (1998)

R | 119 min | Comedy, Romance

69 Metascore

A man gets a chance to meet up with his dream girl from high school, even though his date with her back then was a complete disaster.

Directors: Bobby Farrelly, Peter Farrelly | Stars: Cameron Diaz, Matt Dillon, Ben Stiller, Lee Evans

Votes: 329,068 | Gross: $176.48M

49. Gentlemen Prefer Blondes (1953)

Approved | 91 min | Comedy, Musical, Romance

Showgirls Lorelei Lee and Dorothy Shaw travel to Paris, pursued by a private detective hired by the suspicious father of Lorelei's fiancé, as well as a rich, enamored old man and many other doting admirers.

Director: Howard Hawks | Stars: Jane Russell, Marilyn Monroe, Charles Coburn, Elliott Reid

Votes: 43,049 | Gross: $12.00M

50. Cactus Flower (1969)

M | 104 min | Comedy, Romance

67 Metascore

A dentist pretends to be married to avoid commitment, but when he falls for his girlfriend and proposes, he must recruit his lovelorn nurse to pose as his wife.

Director: Gene Saks | Stars: Walter Matthau, Ingrid Bergman, Goldie Hawn, Jack Weston

Votes: 11,897 | Gross: $25.89M

51. Notting Hill (1999)

PG-13 | 124 min | Comedy, Drama, Romance

68 Metascore

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: 342,522 | Gross: $116.09M

52. Pretty Woman (1990)

R | 119 min | Comedy, Romance

51 Metascore

A man in a legal but hurtful business needs an escort for some social events, and hires a beautiful prostitute he meets... only to fall in love.

Director: Garry Marshall | Stars: Richard Gere, Julia Roberts, Jason Alexander, Laura San Giacomo

Votes: 362,990 | Gross: $178.41M

53. The Spectacular Now (2013)

R | 95 min | Drama, Romance

82 Metascore

A hard-partying high school senior's philosophy on life changes when he meets the not-so-typical "nice girl."

Director: James Ponsoldt | Stars: Miles Teller, Shailene Woodley, Kyle Chandler, Jennifer Jason Leigh

Votes: 161,430 | Gross: $6.85M

54. Four Weddings and a Funeral (1994)

R | 117 min | Comedy, Drama, Romance

81 Metascore

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

55. Out of Sight (1998)

R | 123 min | Comedy, Crime, Drama

84 Metascore

A career bank robber breaks out of jail, and shares a moment of mutual attraction with a U.S. Marshal he has kidnapped.

Director: Steven Soderbergh | Stars: George Clooney, Jennifer Lopez, Ving Rhames, Steve Zahn

Votes: 99,374 | Gross: $37.56M

56. Cyborg She (2008)

115 min | Action, Comedy, Romance

A lonely university student develops a romance with a beautiful interesting woman, who turns out to be a cyborg from the future.

Director: Jae-young Kwak | Stars: Haruka Ayase, Keisuke Koide, Risa Ai, Nya Daigo

Votes: 4,251

57. Knocked Up (2007)

R | 129 min | Comedy, Romance

85 Metascore

For fun-loving party animal Ben Stone, the last thing he ever expected was for his one-night stand to show up on his doorstep eight weeks later to tell him she's pregnant with his child.

Director: Judd Apatow | Stars: Seth Rogen, Katherine Heigl, Paul Rudd, Leslie Mann

Votes: 384,825 | Gross: $148.73M

58. Wedding Crashers (2005)

R | 119 min | Comedy, Romance

64 Metascore

John Beckwith and Jeremy Grey, a pair of committed womanizers who sneak into weddings to take advantage of the romantic tinge in the air, find themselves at odds with one another when John meets and falls for Claire Cleary.

Director: David Dobkin | Stars: Owen Wilson, Vince Vaughn, Rachel McAdams, Christopher Walken

Votes: 375,931 | Gross: $209.22M

59. The Holiday (2006)

PG-13 | 136 min | Comedy, Romance

52 Metascore

Two women troubled with guy-problems swap homes in each other's countries, where they each meet a local guy and fall in love.

Director: Nancy Meyers | Stars: Kate Winslet, Cameron Diaz, Jude Law, Jack Black

Votes: 323,175 | Gross: $63.22M

60. Bridget Jones's Diary (2001)

R | 97 min | Comedy, Drama, Romance

66 Metascore

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: 263,949 | Gross: $71.54M

61. The Mask of Zorro (1998)

PG-13 | 136 min | Action, Adventure, Comedy

62 Metascore

A young thief seeking revenge for his brother's death is trained by the once-great, aging Zorro, who is pursuing his own vengeance.

Director: Martin Campbell | Stars: Antonio Banderas, Anthony Hopkins, Catherine Zeta-Jones, José María de Tavira

Votes: 197,900 | Gross: $94.10M

62. While You Were Sleeping (1995)

PG | 103 min | Comedy, Drama, Romance

67 Metascore

A hopelessly romantic Chicago Transit Authority ticket booth operator is mistaken for the fiancée of a comatose patient.

Director: Jon Turteltaub | Stars: Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle

Votes: 114,085 | Gross: $81.06M

63. Can't Buy Me Love (1987)

PG-13 | 94 min | Comedy, Drama, Romance

36 Metascore

An outcast secretly pays the most popular girl in school one thousand dollars to pretend to be his girlfriend for a month.

Director: Steve Rash | Stars: Patrick Dempsey, Amanda Peterson, Courtney Gains, Tina Caspary

Votes: 42,047 | Gross: $31.62M

64. That Touch of Mink (1962)

Approved | 99 min | Comedy, Romance

A rich businessman and a young woman are attracted to each other, but he only wants an affair while she wants to save herself for marriage.

Director: Delbert Mann | Stars: Cary Grant, Doris Day, Gig Young, Audrey Meadows

Votes: 10,880 | Gross: $14.63M

65. How to Lose a Guy in 10 Days (2003)

PG-13 | 116 min | Comedy, Romance

45 Metascore

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: 270,291 | Gross: $105.81M

66. The Ugly Truth (2009)

R | 96 min | Comedy, Romance

28 Metascore

An uptight television producer takes control of a morning show segment on modern relationships hosted by a misogynistic man.

Director: Robert Luketic | Stars: Katherine Heigl, Gerard Butler, Bree Turner, Eric Winter

Votes: 230,518 | Gross: $88.92M

67. He's Just Not That Into You (2009)

PG-13 | 129 min | Comedy, Drama, Romance

47 Metascore

This Baltimore-set movie of interconnecting story arcs deals with the challenges of reading or misreading human behavior.

Director: Ken Kwapis | Stars: Ginnifer Goodwin, Jennifer Aniston, Jennifer Connelly, Morgan Lily

Votes: 182,315 | Gross: $93.95M

68. Kate & Leopold (2001)

PG-13 | 118 min | Comedy, Fantasy, Romance

44 Metascore

An English Duke from 1876 is inadvertently dragged to modern day New York where he falls for a plucky advertising executive.

Director: James Mangold | Stars: Meg Ryan, Hugh Jackman, Liev Schreiber, Breckin Meyer

Votes: 89,109 | Gross: $47.12M

69. Just Friends (I) (2005)

PG-13 | 96 min | Comedy, Romance

47 Metascore

While visiting his hometown during Christmas, a man comes face-to-face with his old high-school crush and best friend--a woman whose rejection of him turned him into a ferocious womanizer.

Director: Roger Kumble | Stars: Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein

Votes: 127,334 | Gross: $32.62M

70. Bridesmaids (I) (2011)

R | 125 min | Comedy

75 Metascore

Competition between the maid of honor and a bridesmaid, over who is the bride's best friend, threatens to upend the life of an out-of-work pastry chef.

Director: Paul Feig | Stars: Kristen Wiig, Maya Rudolph, Rose Byrne, Terry Crews

Votes: 309,352 | Gross: $169.11M

71. This Is 40 (2012)

R | 134 min | Comedy, Drama, Romance

59 Metascore

Pete and Debbie are both about to turn 40, their kids hate each other, both of their businesses are failing, they're on the verge of losing their house, and their relationship is threatening to fall apart.

Director: Judd Apatow | Stars: Paul Rudd, Leslie Mann, Maude Apatow, Iris Apatow

Votes: 150,534 | Gross: $67.54M

72. Green Card (1990)

PG-13 | 107 min | Comedy, Drama, Romance

58 Metascore

A man wanting to stay in the US enters into a marriage of convenience, but it turns into more than that.

Director: Peter Weir | Stars: Gérard Depardieu, Andie MacDowell, Bebe Neuwirth, Gregg Edelman

Votes: 25,852 | Gross: $29.89M

73. How to Save a Marriage and Ruin Your Life (1968)

Not Rated | 102 min | Comedy, Romance

When a carefree bachelor tries to get his best friend to drop his mistress and return to his wife, he discovers that he too has romantic problems.

Director: Fielder Cook | Stars: Dean Martin, Stella Stevens, Eli Wallach, Anne Jackson

Votes: 837

74. Love Exposure (2008)

Unrated | 237 min | Action, Comedy, Drama

78 Metascore

A bizarre love triangle forms between a young Catholic upskirt photographer, a misandric girl and a manipulative cultist.

Director: Sion Sono | Stars: Takahiro Nishijima, Hikari Mitsushima, Sakura Andô, Yutaka Shimizu

Votes: 15,921



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