Best Romantic Comedies
by mckenzyparsons | created - 20 Jan 2014 | updated - 20 Jan 2014 | Public- Instant Watch Options
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1. 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: 175,187 | Gross: $76.81M
2. 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: 385,580 | Gross: $38.18M
3. Benny & Joon (1993)
PG | 98 min | Comedy, Drama, Romance
A mentally ill young woman finds her love in an eccentric man who models himself after Buster Keaton.
Director: Jeremiah S. Chechik | Stars: Johnny Depp, Mary Stuart Masterson, Aidan Quinn, Julianne Moore
Votes: 62,101 | Gross: $23.20M
4. 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: 88,616 | Gross: $40.47M
5. 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: 217,036 | Gross: $57.23M
6. 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: 41,567 | Gross: $28.18M
7. The Princess Diaries (2001)
G | 115 min | Comedy, Family, Romance
Mia Thermopolis has just found out that she is the heir apparent to the throne of Genovia. With her friends Lilly and Michael Moscovitz in tow, she tries to navigate through the rest of her sixteenth year.
Director: Garry Marshall | Stars: Julie Andrews, Anne Hathaway, Hector Elizondo, Heather Matarazzo
Votes: 163,685 | Gross: $108.25M
8. Sydney White (2007)
PG-13 | 108 min | Comedy, Drama, Romance
A modern retelling of Snow White set against students in their freshman year of college in the greek system.
Director: Joe Nussbaum | Stars: Amanda Bynes, Sara Paxton, Matt Long, Jack Carpenter
Votes: 51,285 | Gross: $11.89M
9. 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: 175,873 | Gross: $2.34M
10. A Cinderella Story (2004)
PG | 95 min | Comedy, Family, Romance
Routinely exploited by her wicked stepmother, the downtrodden Samantha Montgomery is excited about the prospect of meeting her Internet beau at the school's Halloween dance.
Director: Mark Rosman | Stars: Hilary Duff, Chad Michael Murray, Jennifer Coolidge, Dan Byrd
Votes: 94,018 | Gross: $51.44M
11. 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: 61,605 | Gross: $17.32M
12. 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: 335,509 | Gross: $179.50M
13. 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: 248,337 | Gross: $96.52M
14. Love Potion No. 9 (1992)
PG-13 | 92 min | Comedy, Fantasy, Romance
Two scientists who are hopeless with the opposite sex experiment with a substance that makes them irresistible to anyone who hears them speak.
Director: Dale Launer | Stars: Tate Donovan, Sandra Bullock, Mary Mara, Dale Midkiff
Votes: 15,215 | Gross: $0.75M
15. Miss Congeniality (2000)
PG-13 | 109 min | Action, Comedy, Crime
An F.B.I. Agent must go undercover in the Miss United States beauty pageant to prevent a group from bombing the event.
Director: Donald Petrie | Stars: Sandra Bullock, Michael Caine, Benjamin Bratt, Candice Bergen
Votes: 230,411 | Gross: $106.81M
16. Miss Congeniality 2: Armed & Fabulous (2005)
PG-13 | 115 min | Action, Comedy, Crime
Gracie Hart abandons the life of a field agent to become the public face of the FBI. Yet, when Cheryl Frasier and Stan Fields are kidnapped, she is determined to rescue them, along with her reluctant partner.
Director: John Pasquin | Stars: Sandra Bullock, Regina King, William Shatner, Enrique Murciano
Votes: 80,308 | Gross: $48.48M
17. 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: 97,591 | Gross: $55.47M
18. Sixteen Candles (1984)
PG | 93 min | Comedy, Romance
A girl's "sweet" sixteenth birthday is anything but special: her family forgets about it, and she suffers from every embarrassment possible.
Director: John Hughes | Stars: Molly Ringwald, Anthony Michael Hall, Justin Henry, Michael Schoeffling
Votes: 126,411 | Gross: $23.69M
19. Charlie Bartlett (2007)
R | 97 min | Comedy, Drama, Romance
A rich kid becomes the self-appointed psychiatrist to the student body of his new high school.
Director: Jon Poll | Stars: Anton Yelchin, Robert Downey Jr., Hope Davis, Kat Dennings
Votes: 66,709 | Gross: $3.95M
20. 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: 76,071 | Gross: $46.01M
21. One for the Money (2012)
PG-13 | 91 min | Action, Comedy, Crime
Unemployed and newly-divorced Stephanie Plum lands a job at her cousin's bail-bond business, where her first assignment puts her on the trail of a wanted local cop from her romantic past.
Director: Julie Anne Robinson | Stars: Katherine Heigl, Jason O'Mara, Daniel Sunjata, John Leguizamo
Votes: 44,123 | Gross: $26.41M
22. In Her Shoes (2005)
PG-13 | 130 min | Comedy, Drama, Romance
Strait-laced Rose breaks off relations with her party girl sister, Maggie, over an indiscretion involving Rose's boyfriend. The chilly atmosphere is broken with the arrival of Ella, the grandmother neither sister knew existed.
Director: Curtis Hanson | Stars: Toni Collette, Cameron Diaz, Shirley MacLaine, Anson Mount
Votes: 65,088 | Gross: $32.88M
23. 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: 144,663 | Gross: $241.44M
24. 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: 64,627 | Gross: $32.67M
25. Mystic Pizza (1988)
R | 104 min | Comedy, Drama, Romance
Three teenage girls come of age while working at a pizza parlor in the Connecticut town of Mystic.
Director: Donald Petrie | Stars: Annabeth Gish, Julia Roberts, Lili Taylor, Vincent D'Onofrio
Votes: 32,491 | Gross: $12.79M
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