romantic comedies and chick flicks
by maxmp5 | created - 25 Aug 2014 | updated - 25 Aug 2014 | Public- Instant Watch Options
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1. Simply Irresistible (1999)
PG-13 | 96 min | Comedy, Drama, Fantasy
A magical crab works wonders for a terrible chef's culinary skills, leading her towards the man of her dreams.
Director: Mark Tarlov | Stars: Sarah Michelle Gellar, Sean Patrick Flanery, Patricia Clarkson, Dylan Baker
Votes: 14,923 | Gross: $4.39M
2. For Love or Money (1993)
PG | 96 min | Comedy, Drama, Romance
Doug, a concierge at a luxury Manhattan hotel, saves all his tips toward his plan for a hotel. A potential investor seduces the girl Doug loves with false promises of leaving his wife. Doug's dilemma: hotel project or girl?
Director: Barry Sonnenfeld | Stars: Michael J. Fox, Gabrielle Anwar, Anthony Higgins, Michael Tucker
Votes: 15,429 | Gross: $11.00M
3. No Reservations (2007)
PG | 104 min | Comedy, Drama, Romance
The life of a top chef changes when she becomes the guardian of her young niece.
Director: Scott Hicks | Stars: Catherine Zeta-Jones, Aaron Eckhart, Abigail Breslin, Patricia Clarkson
Votes: 78,812 | Gross: $43.11M
4. Pretty Woman (1990)
R | 119 min | Comedy, Romance
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: 362,481 | Gross: $178.41M
5. Doc Hollywood (1991)
PG-13 | 104 min | Comedy, Drama, Romance
A young doctor on his way across the country to a job interview crashes his car in a small town and is sentenced to work for several days at the town hospital.
Director: Michael Caton-Jones | Stars: Michael J. Fox, Julie Warner, Barnard Hughes, Woody Harrelson
Votes: 40,302 | Gross: $54.83M
6. 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: 190,898 | Gross: $126.53M
7. As Good as It Gets (1997)
PG-13 | 139 min | Comedy, Drama, Romance
A single mother and waitress, a misanthropic author, and a gay artist form an unlikely friendship after the artist is assaulted in a robbery.
Director: James L. Brooks | Stars: Jack Nicholson, Helen Hunt, Greg Kinnear, Cuba Gooding Jr.
Votes: 318,482 | Gross: $148.48M
8. There's Something About Mary (1998)
R | 119 min | Comedy, Romance
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: 328,934 | Gross: $176.48M
9. What Women Want (2000)
PG-13 | 127 min | Comedy, Fantasy, Romance
A cocky, chauvinistic advertising executive magically acquires the ability to hear what women are thinking.
Director: Nancy Meyers | Stars: Mel Gibson, Helen Hunt, Marisa Tomei, Alan Alda
Votes: 222,380 | Gross: $182.81M
10. Get Over It (2001)
PG-13 | 87 min | Comedy, Romance
A high school senior's girlfriend breaks up with him. His friends try to make him think of something else. His friend's sister Kelly helps him with the school musical. Spending time with Kelly has an effect.
Director: Tommy O'Haver | Stars: Kirsten Dunst, Ben Foster, Melissa Sagemiller, Sisqó
Votes: 20,026 | Gross: $11.58M
11. The Wedding Planner (2001)
PG-13 | 103 min | Comedy, Romance
Mary Fiore is San Francisco's most successful supplier of romance and glamor. She knows all the tricks. She knows all the rules. But then she breaks the most important rule of all: she falls in love with the groom.
Director: Adam Shankman | Stars: Jennifer Lopez, Matthew McConaughey, Bridgette Wilson-Sampras, Justin Chambers
Votes: 86,543 | Gross: $60.40M
12. 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: 270,080 | Gross: $105.81M
13. 13 Going on 30 (2004)
PG-13 | 98 min | Comedy, Fantasy, Romance
Unpopular schoolgirl Jenna Rink makes an unusual wish on her birthday. Miraculously, her wish comes true and the 13-year-old Jenna wakes up the next day as a 30-year-old woman.
Director: Gary Winick | Stars: Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis
Votes: 216,935 | Gross: $57.23M
14. 50 First Dates (2004)
PG-13 | 99 min | Comedy, Drama, Romance
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: 382,234 | Gross: $120.91M
15. Wimbledon (2004)
PG-13 | 98 min | Comedy, Romance, Sport
A pro tennis player has lost his ambition and has fallen in rank to 119. Fortunately for him, he meets a young player on the women's circuit who helps him recapture his focus for Wimbledon.
Director: Richard Loncraine | Stars: Kirsten Dunst, Paul Bettany, Jon Favreau, Sam Neill
Votes: 66,633 | Gross: $17.00M
16. She's the Man (2006)
PG-13 | 105 min | Comedy, Romance, Sport
When her brother decides to ditch for a couple weeks, Viola heads over to his elite boarding school, disguised as him, and proceeds to fall for his school's star soccer player, and soon learns she's not the only one with romantic troubles.
Director: Andy Fickman | Stars: Amanda Bynes, Laura Ramsey, Channing Tatum, Vinnie Jones
Votes: 175,839 | Gross: $2.34M
17. 27 Dresses (2008)
PG-13 | 111 min | Comedy, Romance
After serving as a bridesmaid 27 times, a young woman wrestles with the idea of standing by her sister's side as her sibling marries the man she's secretly in love with.
Director: Anne Fletcher | Stars: Katherine Heigl, James Marsden, Malin Akerman, Brian Kerwin
Votes: 175,151 | Gross: $76.81M
18. Made of Honor (2008)
PG-13 | 101 min | Comedy, Romance
Hannah surprises Tom, her best friend who is secretly in love with her, with the news of her engagement to a wealthy man. Things take a complicated turn when she asks Tom to be her maid of honor.
Director: Paul Weiland | Stars: Patrick Dempsey, Michelle Monaghan, Kevin McKidd, Kadeem Hardison
Votes: 76,056 | Gross: $46.01M
19. When in Rome (2010)
PG-13 | 91 min | Comedy, Romance
Beth is an ambitious young New Yorker who is completely unlucky in love. On a whirlwind trip to Rome, she impulsively steals some coins from a reputed fountain of love, and is then aggressively pursued by a band of suitors.
Director: Mark Steven Johnson | Stars: Kristen Bell, Josh Duhamel, Anjelica Huston, Danny DeVito
Votes: 64,618 | Gross: $32.67M
20. Romancing the Stone (1984)
PG | 106 min | Action, Adventure, Comedy
A mousy romance novelist sets off for Colombia to ransom her kidnapped sister, and soon finds herself in the middle of a dangerous adventure hunting for treasure with a mercenary rogue.
Director: Robert Zemeckis | Stars: Michael Douglas, Kathleen Turner, Danny DeVito, Zack Norman
Votes: 103,345 | Gross: $76.57M
21. Pretty in Pink (1986)
PG-13 | 97 min | Comedy, Drama, Romance
A poor girl must choose between the affections of dating her childhood sweetheart or a rich but sensitive playboy.
Director: Howard Deutch | Stars: Molly Ringwald, Jon Cryer, Harry Dean Stanton, Annie Potts
Votes: 88,596 | Gross: $40.47M
22. Baby Boom (1987)
PG | 110 min | Comedy, Drama, Romance
The life of super-yuppie J.C. is thrown into turmoil when she inherits a baby from a distant relative.
Director: Charles Shyer | Stars: Diane Keaton, Sam Shepard, Harold Ramis, Kristina Kennedy
Votes: 19,164 | Gross: $26.71M
23. 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: 68,537 | Gross: $80.64M
24. Overboard (1987)
PG | 112 min | Comedy, Romance
A cruel but beautiful heiress mocks and cheats a hired carpenter. When she gets amnesia after an accident, he decides to introduce her to regular life by convincing her that they're husband and wife.
Director: Garry Marshall | Stars: Goldie Hawn, Kurt Russell, Edward Herrmann, Katherine Helmond
Votes: 67,888 | Gross: $26.71M
25. The Princess Bride (1987)
PG | 98 min | Adventure, Comedy, Family
A bedridden boy's grandfather reads him the story of a farmboy-turned-pirate who encounters numerous obstacles, enemies and allies in his quest to be reunited with his true love.
Director: Rob Reiner | Stars: Cary Elwes, Mandy Patinkin, Robin Wright, Chris Sarandon
Votes: 451,012 | Gross: $30.86M
26. 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: 223,616 | Gross: $128.15M
27. Working Girl (1988)
R | 113 min | Comedy, Drama, Romance
When a secretary's idea is stolen by her boss, she seizes an opportunity to steal it back by pretending she has her boss' job.
Director: Mike Nichols | Stars: Melanie Griffith, Harrison Ford, Sigourney Weaver, Alec Baldwin
Votes: 62,420 | Gross: $64.00M
28. 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: 242,764 | Gross: $92.82M
29. Green Card (1990)
PG-13 | 107 min | Comedy, Drama, Romance
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: 25,846 | Gross: $29.89M
30. Boomerang (1992)
R | 117 min | Comedy, Drama, Romance
A successful executive and womanizer finds his lifestyle choices have turned back on him when his new female boss turns out to be an even bigger deviant than he is.
Director: Reginald Hudlin | Stars: Eddie Murphy, Robin Givens, Halle Berry, David Alan Grier
Votes: 31,385 | Gross: $70.10M
31. The Cutting Edge (1992)
PG | 101 min | Comedy, Drama, Romance
A temperamental figure skater and an arrogant former hockey player attempt to win the Olympic Gold Medal as a figure skating pairs team.
Director: Paul Michael Glaser | Stars: D.B. Sweeney, Moira Kelly, Roy Dotrice, Terry O'Quinn
Votes: 22,359 | Gross: $25.11M
32. 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: 166,183 | Gross: $52.70M
33. Only You (1994)
PG | 109 min | Comedy, Romance
As a teen, Faith was told that her destiny is a man named Damon Bradley. Years later - Faith is about to marry another man - a Damon Bradley calls to wish them all the best. Faith blows off the wedding and follows Damon to Italy.
Director: Norman Jewison | Stars: Marisa Tomei, Robert Downey Jr., Bonnie Hunt, Joaquim de Almeida
Votes: 25,688 | Gross: $20.04M
34. French Kiss (1995)
PG-13 | 111 min | Comedy, Drama, Romance
A woman flying to France to confront her straying fiance gets into trouble when the charming crook seated next to her uses her for smuggling.
Director: Lawrence Kasdan | Stars: Meg Ryan, Kevin Kline, Timothy Hutton, Jean Reno
Votes: 53,035 | Gross: $38.90M
35. Mighty Aphrodite (1995)
R | 95 min | Comedy, Fantasy, Romance
When he discovers his adopted son is a genius, a New York sportswriter seeks out the boy's birth mother: a ditzy porn star and prostitute.
Director: Woody Allen | Stars: Woody Allen, Mira Sorvino, Pamela Blair, Rene Ceballos
Votes: 42,812 | Gross: $6.70M
36. Sabrina (1995)
PG | 127 min | Comedy, Drama, Romance
An ugly duckling having undergone a remarkable change, still harbors feelings for her crush: a carefree playboy, but not before his business-focused brother has something to say about it.
Director: Sydney Pollack | Stars: Harrison Ford, Julia Ormond, Greg Kinnear, Nancy Marchand
Votes: 44,448 | Gross: $53.67M
37. While You Were Sleeping (1995)
PG | 103 min | Comedy, Drama, Romance
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: 114,024 | Gross: $81.06M
38. One Fine Day (1996)
PG | 108 min | Comedy, Drama, Romance
The lives of two strangers and their young children unexpectedly intersect on one hectic, stressful day in New York City.
Director: Michael Hoffman | Stars: Michelle Pfeiffer, George Clooney, Mae Whitman, Alex D. Linz
Votes: 48,521 | Gross: $46.15M
39. The Truth About Cats & Dogs (1996)
PG-13 | 97 min | Comedy, Romance
A successful veternarian & radio show host with low self-esteem asks her model friend to impersonate her when a handsome man wants to see her.
Director: Michael Lehmann | Stars: Uma Thurman, Janeane Garofalo, Ben Chaplin, Jamie Foxx
Votes: 29,095 | Gross: $34.07M
40. Fools Rush In (1997)
PG-13 | 109 min | Comedy, Drama, Romance
After a one-night stand with Alex, Isabel realizes that she is pregnant and they decide to get married. However, along with the marriage comes compromise of one's own cultural traditions.
Director: Andy Tennant | Stars: Matthew Perry, Salma Hayek, Jon Tenney, Carlos Gómez
Votes: 39,635 | Gross: $29.29M
41. 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: 155,425 | Gross: $127.12M
42. Out to Sea (1997)
PG-13 | 106 min | Comedy, Romance
A failed gambler, intent on meeting a rich widow, tricks his widowed brother-in-law into boarding a cruise ship as dance hosts.
Director: Martha Coolidge | Stars: Jack Lemmon, Walter Matthau, Dyan Cannon, Gloria DeHaven
Votes: 9,518 | Gross: $27.97M
43. Picture Perfect (1997)
PG-13 | 101 min | Comedy, Drama, Romance
A young advertising executive's life becomes increasingly complicated when, in order to impress her boss, she pretends to be engaged to a man she has just met.
Director: Glenn Gordon Caron | Stars: Jennifer Aniston, Jay Mohr, Kevin Bacon, Olympia Dukakis
Votes: 21,460 | Gross: $31.06M
44. Overnight Delivery (1998 Video)
PG-13 | 87 min | Comedy, Romance
Wyatt writes an angry letter to his girlfriend, believing she's dating Ricker. Ricker's a dog. Helped by stripper Ivy, he tries to get the letter off a truck the next 24 hours.
Director: Jason Bloom | Stars: Paul Rudd, Christine Taylor, Reese Witherspoon, Sarah Silverman
Votes: 7,029
45. The Wedding Singer (1998)
PG-13 | 97 min | Comedy, Music, Romance
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: 162,340 | Gross: $80.25M
46. 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: 229,706 | Gross: $115.82M
47. 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: 385,377 | Gross: $38.18M
48. Never Been Kissed (1999)
PG-13 | 107 min | Comedy, Drama, Romance
A newspaper reporter enrolls in high school as part of research for a story.
Director: Raja Gosnell | Stars: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon
Votes: 97,579 | Gross: $55.47M
49. 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: 342,333 | Gross: $116.09M
50. Runaway Bride (1999)
PG | 116 min | Comedy, Romance
A reporter is assigned to write a story about a woman who has left a string of fiancés at the altar.
Director: Garry Marshall | Stars: Julia Roberts, Richard Gere, Joan Cusack, Hector Elizondo
Votes: 104,511 | Gross: $152.26M
51. She's All That (1999)
PG-13 | 95 min | Comedy, Romance
A high school jock makes a bet that he can turn an unattractive girl into the school's prom queen.
Director: Robert Iscove | Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker
Votes: 103,835 | Gross: $63.37M
52. The Bachelor (1999)
PG-13 | 101 min | Comedy, Romance
A commitment-phobic man goes in search of a bride, including his fed-up girlfriend, to inherit his grandfather's one hundred million dollar inheritance.
Director: Gary Sinyor | Stars: Chris O'Donnell, Renée Zellweger, Artie Lange, Edward Asner
Votes: 19,015 | Gross: $21.76M
53. Three to Tango (1999)
PG-13 | 98 min | Comedy, Romance
A rich businessman's assumption that his new colleague is gay leads him to ask the man to keep an eye on his mistress. However, the man is not gay--and he begins to fall for the woman himself.
Director: Damon Santostefano | Stars: Neve Campbell, Matthew Perry, Dylan McDermott, Oliver Platt
Votes: 20,084 | Gross: $10.54M
54. Coyote Ugly (2000)
PG-13 | 100 min | Comedy, Drama, Music
Aspiring songwriter Violet Sanford, after getting a job at a women-run NYC bar that teases its male patrons, comes out of her shell.
Director: David McNally | Stars: Piper Perabo, Adam Garcia, John Goodman, Maria Bello
Votes: 120,945 | Gross: $60.79M
55. Keeping the Faith (2000)
PG-13 | 128 min | Comedy, Drama, Romance
Two friends, a priest and a rabbi, fall in love with the same woman they knew in their youth, but the religious position of both men denies them romance.
Director: Edward Norton | Stars: Ben Stiller, Edward Norton, Jenna Elfman, Anne Bancroft
Votes: 53,232 | Gross: $37.05M
56. Return to Me (2000)
PG | 115 min | Comedy, Drama, Romance
A man who falls in love with the woman who received his wife's heart must decide which woman it is who holds his heart.
Director: Bonnie Hunt | Stars: David Duchovny, Minnie Driver, Carroll O'Connor, Robert Loggia
Votes: 22,793 | Gross: $32.66M
57. 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: 263,634 | Gross: $71.54M
58. Head Over Heels (2001)
PG-13 | 86 min | Comedy, Mystery, Romance
A young woman is attracted to a man despite her thinking she's seen him kill someone.
Director: Mark Waters | Stars: Monica Potter, Freddie Prinze Jr., Shalom Harlow, Ivana Milicevic
Votes: 15,299 | Gross: $10.40M
59. Kate & Leopold (2001)
PG-13 | 118 min | Comedy, Fantasy, Romance
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: 89,085 | Gross: $47.12M
60. Legally Blonde (2001)
PG-13 | 96 min | Comedy, Romance
Elle Woods, a fashionable sorority queen, is dumped by her boyfriend. She decides to follow him to law school. While she is there, she figures out that there is more to her than just looks.
Director: Robert Luketic | Stars: Reese Witherspoon, Luke Wilson, Selma Blair, Matthew Davis
Votes: 248,233 | Gross: $96.52M
61. Serendipity (2001)
PG-13 | 90 min | Comedy, Romance
A couple search for each other years after the night they first met, fell in love, and separated, convinced that one day they'd end up together.
Director: Peter Chelsom | Stars: John Cusack, Kate Beckinsale, Jeremy Piven, Bridget Moynahan
Votes: 121,383 | Gross: $50.29M
62. Shallow Hal (2001)
PG-13 | 114 min | Comedy, Drama, Fantasy
A shallow man falls in love with a 300-pound woman because of her inner beauty.
Directors: Bobby Farrelly, Peter Farrelly | Stars: Jack Black, Gwyneth Paltrow, Jason Alexander, Joe Viterelli
Votes: 144,797 | Gross: $70.84M
63. The Brothers (2001)
R | 106 min | Comedy, Drama, Romance
Four friends begin to question women and relationships when one of them announces impending nuptials.
Director: Gary Hardwick | Stars: Morris Chestnut, Shemar Moore, D.L. Hughley, Bill Bellamy
Votes: 5,075 | Gross: $27.46M
64. Two Can Play That Game (2001)
R | 90 min | Comedy, Romance
An arrogant career woman plays a series of heartless mind-games with her boyfriend to "put him in line," only to discover that he has a few tricks up his own sleeve.
Director: Mark Brown | Stars: Vivica A. Fox, Morris Chestnut, Anthony Anderson, Gabrielle Union
Votes: 7,372 | Gross: $22.24M
65. 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: 144,649 | Gross: $241.44M
66. Serving Sara (2002)
PG-13 | 99 min | Comedy, Romance
A process server tries to serve an elusive female target.
Director: Reginald Hudlin | Stars: Matthew Perry, Elizabeth Hurley, Bruce Campbell, Vincent Pastore
Votes: 18,818 | Gross: $16.93M
67. Sweet Home Alabama (2002)
PG-13 | 108 min | Comedy, Romance
A young woman who has reinvented herself as a New York City socialite must return home to Alabama to obtain a divorce from her husband after seven years of separation.
Director: Andy Tennant | Stars: Reese Witherspoon, Patrick Dempsey, Josh Lucas, Candice Bergen
Votes: 123,609 | Gross: $127.22M
68. The Sweetest Thing (2002)
R | 84 min | Comedy, Romance
Christina Walters spent years avoiding men, then suddenly met her perfect match while hanging with her best friends, Courtney and Jane. When she finds out that he has left town, she and Courtney set out on a trip.
Director: Roger Kumble | Stars: Cameron Diaz, Thomas Jane, Christina Applegate, Lillian Adams
Votes: 62,463 | Gross: $24.72M
69. Two Weeks Notice (2002)
PG-13 | 101 min | Comedy, Romance
A lawyer decides that she's used too much like a nanny by her boss, so she walks out on him.
Director: Marc Lawrence | Stars: Sandra Bullock, Hugh Grant, Alicia Witt, Dana Ivey
Votes: 125,943 | Gross: $93.35M
70. Along Came Polly (2004)
PG-13 | 90 min | Comedy, Romance
A buttoned-up newlywed finds his strictly organized life descend into chaos when he falls in love with an old classmate.
Director: John Hamburg | Stars: Ben Stiller, Jennifer Aniston, Debra Messing, Philip Seymour Hoffman
Votes: 143,670 | Gross: $88.10M
71. Deliver Us from Eva (2003)
R | 105 min | Comedy, Drama, Romance
Eva doesn't let her 3 sisters' men push them around. She's always butting in. How to pacify Eva? Find her a man. The men pay a playboy to be that man. The problem is - he falls in love with Eva.
Director: Gary Hardwick | Stars: Gabrielle Union, LL Cool J, Essence Atkins, Duane Martin
Votes: 7,728 | Gross: $17.33M
72. Legally Blonde 2: Red, White & Blonde (2003)
PG-13 | 95 min | Comedy
Elle Woods heads to Washington, D.C. to join the staff of a Representative in order to pass a bill to ban animal testing.
Director: Charles Herman-Wurmfeld | Stars: Reese Witherspoon, Sally Field, Bob Newhart, Regina King
Votes: 72,730 | Gross: $90.19M
73. Love Actually (2003)
R | 135 min | Comedy, Drama, Romance
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: 531,563 | Gross: $59.70M
74. 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: 129,200 | Gross: $124.73M
75. The Fighting Temptations (2003)
PG-13 | 123 min | Comedy, Drama, Music
A New York advertising executive travels to a small Southern town to collect an inheritance but finds he must create a gospel choir and lead it to success before he can collect.
Director: Jonathan Lynn | Stars: Cuba Gooding Jr., Beyoncé, Mike Epps, Nigel Washington
Votes: 7,621 | Gross: $30.24M
76. Under the Tuscan Sun (2003)
PG-13 | 113 min | Comedy, Drama, Romance
Frances Mayes, a 35-year-old San Francisco writer, gets a divorce that leaves her with terminal writer's block and depression. Later, she decides to buy a house in Tuscany in order to change her life.
Director: Audrey Wells | Stars: Diane Lane, Raoul Bova, Sandra Oh, Lindsay Duncan
Votes: 59,590 | Gross: $43.61M
77. Bride & Prejudice (2004)
PG-13 | 122 min | Comedy, Drama, Musical
A modern adaptation of Jane Austen's classic novel, Pride and Prejudice, that features the lives of four unmarried daughters in an Indian family.
Director: Gurinder Chadha | Stars: Martin Henderson, Aishwarya Rai Bachchan, Nadira Babbar, Anupam Kher
Votes: 21,669 | Gross: $6.61M
78. Bridget Jones: The Edge of Reason (2004)
R | 108 min | Comedy, Drama, Romance
After finding love, Bridget Jones questions if she really has everything she'd ever dreamed of having.
Director: Beeban Kidron | Stars: Renée Zellweger, Colin Firth, Hugh Grant, Gemma Jones
Votes: 122,468 | Gross: $40.23M
79. The Prince and Me (2004)
PG | 111 min | Comedy, Family, Romance
At college Paige meets Eddie, a student from Denmark, whom she first dislikes but later accepts, likes, and loves; he proves to be Crown Prince Edvard. Paige follows him to Copenhagen, and he follows her back to school with a plan.
Director: Martha Coolidge | Stars: Julia Stiles, Luke Mably, Miranda Richardson, Ben Miller
Votes: 41,563 | Gross: $28.18M
80. Win a Date with Tad Hamilton! (2004)
PG-13 | 95 min | Comedy, Romance
A small-town girl wins a date with a male celebrity through a contest. When the date goes better than expected, a love triangle forms between the girl, the male celebrity, and the girl's best friend.
Director: Robert Luketic | Stars: Kate Bosworth, Josh Duhamel, Topher Grace, Nathan Lane
Votes: 29,433 | Gross: $17.07M
81. A Lot Like Love (2005)
PG-13 | 107 min | Comedy, Drama, Romance
Unacquainted Emily and Oliver join the mile-high club together on the way from LAX to NYC--end of story. Except that they keep meeting constantly over the next seven years..
Director: Nigel Cole | Stars: Ashton Kutcher, Amanda Peet, Taryn Manning, Aimee Garcia
Votes: 71,209 | Gross: $21.84M
82. Fever Pitch (1997)
R | 102 min | Comedy, Drama, Romance
A sports fan's romantic courtship clashes with his obsession with his favorite football team.
Director: David Evans | Stars: Colin Firth, Ruth Gemmell, Luke Aikman, Bea Guard
Votes: 11,706 | Gross: $0.01M
83. Hitch (I) (2005)
PG-13 | 118 min | Comedy, Romance
A smooth-talking man falls for a hardened columnist while helping a shy accountant woo a beautiful heiress.
Director: Andy Tennant | Stars: Will Smith, Eva Mendes, Kevin James, Amber Valletta
Votes: 335,467 | Gross: $179.50M
84. Imagine Me & You (2005)
R | 90 min | Comedy, Drama, Romance
A newlywed bride becomes infatuated with another woman who questions her sexual orientation, promoting a stir among the bride's family and friends.
Director: Ol Parker | Stars: Piper Perabo, Lena Headey, Matthew Goode, Celia Imrie
Votes: 35,997 | Gross: $0.67M
85. Just Friends (I) (2005)
PG-13 | 96 min | Comedy, Romance
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: 127,303 | Gross: $32.62M
86. Just Like Heaven (2005)
PG-13 | 95 min | Comedy, Drama, Fantasy
A lonely landscape architect falls for the spirit of the beautiful woman who used to live in his new apartment.
Director: Mark Waters | Stars: Reese Witherspoon, Mark Ruffalo, Donal Logue, Dina Spybey-Waters
Votes: 117,373 | Gross: $48.32M
87. Little Manhattan (2005)
PG | 90 min | Comedy, Family, Romance
A 10-year-old boy and an 11-year-old girl find love in New York City.
Director: Mark Levin | Stars: Josh Hutcherson, Charlotte Ray Rosenberg, Bradley Whitford, Cynthia Nixon
Votes: 24,791 | Gross: $0.38M
88. Monster-in-Law (2005)
PG-13 | 101 min | Comedy, Romance
The love life of Charlotte is reduced to an endless string of disastrous blind dates, until she meets the perfect man, Kevin. Unfortunately, his merciless mother will do anything to destroy their relationship.
Director: Robert Luketic | Stars: Jennifer Lopez, Michael Vartan, Jane Fonda, Wanda Sykes
Votes: 65,562 | Gross: $82.93M
89. Must Love Dogs (2005)
PG-13 | 98 min | Comedy, Romance
A thirty-something preschool teacher looks to the personals for a change of pace and a relationship, with hilarious results.
Director: Gary David Goldberg | Stars: Diane Lane, John Cusack, Elizabeth Perkins, Christopher Plummer
Votes: 33,065 | Gross: $43.89M
90. 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: 467,183 | Gross: $109.45M
91. The Wedding Date (2005)
PG-13 | 90 min | Comedy, Romance
Single-girl anxiety causes Kat Ellis to hire a male escort to pose as her boyfriend at her sister's wedding. Her plan, an attempt to dupe her ex-fiancé, who dumped her a couple years prior, proves to be her undoing.
Director: Clare Kilner | Stars: Dermot Mulroney, Debra Messing, Jack Davenport, Amy Adams
Votes: 56,306 | Gross: $31.73M
92. Wedding Crashers (2005)
R | 119 min | Comedy, Romance
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: 375,825 | Gross: $209.22M
93. Rumor Has It... (2005)
PG-13 | 97 min | Comedy, Drama, Romance
Sarah Huttinger is a woman who learns that her family was the inspiration for the book and film "The Graduate" -- and that she just might be the offspring of the well-documented event.
Director: Rob Reiner | Stars: Jennifer Aniston, Mark Ruffalo, Shirley MacLaine, Kevin Costner
Votes: 61,670 | Gross: $43.00M
94. Failure to Launch (2006)
PG-13 | 97 min | Comedy, Romance
A thirty-something is still living with his parents until they hire an interventionist to help him graduate out of the house. That's when the fun begins.
Director: Tom Dey | Stars: Matthew McConaughey, Sarah Jessica Parker, Kathy Bates, Terry Bradshaw
Votes: 85,839 | Gross: $88.72M
95. It's a Boy Girl Thing (2006)
PG-13 | 95 min | Comedy, Fantasy, Romance
Sworn enemies find themselves in each other's bodies, and use this to ruin each other's lives.
Director: Nick Hurran | Stars: Samaire Armstrong, Kevin Zegers, Sherry Miller, Robert Joy
Votes: 42,823
96. Just My Luck (2006)
PG-13 | 103 min | Comedy, Fantasy, Romance
Manhattanite Ashley is known to many as the luckiest woman around. After a chance encounter with a down-and-out young man, however, she realizes that she's swapped her fortune for his.
Director: Donald Petrie | Stars: Lindsay Lohan, Chris Pine, Samaire Armstrong, Bree Turner
Votes: 61,595 | Gross: $17.32M
97. Love and Other Disasters (2006)
R | 90 min | Comedy, Drama, Romance
An American intern at U.K. Vogue helps her friends find love.
Director: Alek Keshishian | Stars: Brittany Murphy, Matthew Rhys, Catherine Tate, Santiago Cabrera
Votes: 14,730
98. My Super Ex-Girlfriend (2006)
PG-13 | 96 min | Comedy, Romance, Sci-Fi
When a regular guy dumps a superhero for her neediness, she uses her powers to make his life a living hell.
Director: Ivan Reitman | Stars: Uma Thurman, Luke Wilson, Anna Faris, Rainn Wilson
Votes: 67,017 | Gross: $22.53M
99. The Break-Up (2006)
PG-13 | 106 min | Comedy, Drama, Romance
A couple's break-up proceeds to get uglier and nastier by the moment as each tries to keep their luxurious condo from the other.
Director: Peyton Reed | Stars: Jennifer Aniston, Vince Vaughn, Jon Favreau, Joey Lauren Adams
Votes: 138,997 | Gross: $118.70M
100. The Holiday (2006)
PG-13 | 136 min | Comedy, Romance
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: 323,004 | Gross: $63.22M
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