ULTIMATE ROMANTIC COMEDY FILMS
by shane-pompey | created - 29 Jan 2013 | updated - 16 Jul 2013 | Public- Instant Watch Options
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1. Dan in Real Life (I) (2007)
PG-13 | 98 min | Comedy, Drama, Romance
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: 106,978 | Gross: $47.64M
2. 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: 39,607 | Gross: $29.29M
3. 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: 190,773 | Gross: $126.53M
4. City of Angels (1998)
PG-13 | 114 min | Drama, Fantasy, Romance
An angel on Earth, a doctor unable to believe, a patient with a secret, a love story made in Heaven.
Director: Brad Silberling | Stars: Nicolas Cage, Meg Ryan, Andre Braugher, Dennis Franz
Votes: 127,734 | Gross: $78.69M
5. 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: 242,592 | Gross: $92.82M
6. 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: 31,361 | Gross: $70.10M
7. The Proposal (I) (2009)
PG-13 | 108 min | Comedy, Drama, Romance
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: 360,075 | Gross: $163.96M
8. 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: 229,547 | Gross: $115.82M
9. 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: 121,320 | Gross: $50.29M
10. 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: 162,224 | Gross: $80.25M
11. 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: 361,953 | Gross: $178.41M
12. Maid in Manhattan (2002)
PG-13 | 105 min | Comedy, Drama, Romance
A Senatorial candidate falls for a hotel maid, thinking she is a socialite, when he sees her trying on a wealthy woman's dress.
Director: Wayne Wang | Stars: Jennifer Lopez, Ralph Fiennes, Natasha Richardson, Stanley Tucci
Votes: 96,159 | Gross: $94.01M
13. 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: 65,522 | Gross: $82.93M
14. Knocked Up (2007)
R | 129 min | Comedy, Romance
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: 384,460 | Gross: $148.73M
15. 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: 216,677 | Gross: $57.23M
16. 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: 269,803 | Gross: $105.81M
17. Forgetting Sarah Marshall (2008)
R | 111 min | Comedy, Drama, Romance
Devastated Peter takes a Hawaiian vacation in order to deal with the recent break-up with his TV star girlfriend, Sarah. Little does he know, Sarah's traveling to the same resort as her ex - and she's bringing along her new boyfriend.
Director: Nicholas Stoller | Stars: Kristen Bell, Jason Segel, Paul Rudd, Mila Kunis
Votes: 302,371 | Gross: $63.17M
18. 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: 381,960 | Gross: $120.91M
19. Happy Gilmore (1996)
PG-13 | 92 min | Comedy, Sport
After his grandmothers house is repossessed by the IRS, bad tempered hockey player takes his talents to golf to earn the big bucks and get his grandmothers house back.
Director: Dennis Dugan | Stars: Adam Sandler, Christopher McDonald, Julie Bowen, Frances Bay
Votes: 248,274 | Gross: $38.62M
20. 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: 466,764 | Gross: $109.45M
21. Say Anything (1989)
PG-13 | 100 min | Comedy, Drama, Romance
A noble underachiever and a beautiful valedictorian fall in love the summer before she goes off to college.
Director: Cameron Crowe | Stars: John Cusack, Ione Skye, John Mahoney, Lili Taylor
Votes: 95,883 | Gross: $20.78M
22. 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: 222,238 | Gross: $182.81M
23. Couples Retreat (2009)
PG-13 | 113 min | Comedy
A comedy centered around four couples who settle into a tropical-island resort for a vacation. While one of the couples is there to work on the marriage, the others fail to realize that participation in the resort's therapy sessions is not optional.
Director: Peter Billingsley | Stars: Vince Vaughn, Malin Akerman, Jon Favreau, Jason Bateman
Votes: 114,822 | Gross: $109.21M
24. 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: 322,840 | Gross: $63.22M
25. Friends with Benefits (2011)
R | 109 min | Comedy, Romance
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: 394,402 | Gross: $55.80M
26. Spanglish (2004)
PG-13 | 131 min | Comedy, Drama, Romance
A woman and her daughter emigrate from Mexico for a better life in America, where they start working for a family whose patriarch is a newly celebrated chef with an insecure wife.
Director: James L. Brooks | Stars: Adam Sandler, Téa Leoni, Paz Vega, Cloris Leachman
Votes: 88,525 | Gross: $42.73M
27. Valentine's Day (I) (2010)
PG-13 | 125 min | Comedy, Romance
Intertwining couples and singles in Los Angeles break-up and make-up based on the pressures and expectations of Valentine's Day.
Director: Garry Marshall | Stars: Julia Roberts, Jamie Foxx, Anne Hathaway, Jessica Alba
Votes: 125,386 | Gross: $110.49M
28. Bridesmaids (I) (2011)
R | 125 min | Comedy
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: 309,082 | Gross: $169.11M
29. 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: 144,717 | Gross: $70.84M
30. Zack and Miri Make a Porno (2008)
R | 101 min | Comedy, Romance
Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each other than they previously thought.
Director: Kevin Smith | Stars: Seth Rogen, Elizabeth Banks, Craig Robinson, Gerry Bednob
Votes: 182,273 | Gross: $31.46M
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