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The Greatest Guilty Pleasure Romantic Comedies 

Alan Smithee
Updated October 2, 2019 443 votes 54 voters 2.3k views 32 items

List Rules Vote for the best guilty pleasure romcoms (that you enjoy despite the cheese factor).

Cheesy romantic comedies are great for a quick pick-me-up if you're feeling unlucky in love or just need to switch your mind into off mode. Not every guilty pleasure rom com is an inherently bad film, but absurd plots and corny dialogue can make you feel just a tad embarrassed for loving the genre. Nevertheless, such films are often the perfect cure for what ails you! 

Some dumb romantic comedies constitute guilty pleasures. Whether it's a once renowned film that has aged horribly or a film that was never great to begin with, bad movies can still be fun. Other indulgent romcoms are simply lighthearted and easy, with plot lines that don't challenge you all that much. Whatever you're looking for in terms of guilty pleasures, browse this list to find the best option for you! 

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1
10 Things I Hate About Y... is listed (or ranked) 1 on the list The Greatest Guilty Pleasure Romantic Comedies
Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger

Released: 1999

Directed by: Gil Junger

10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and a modern retelling of William Shakespeare's The Taming of the Shrew. After finding out his crush ...more

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2
Clueless is listed (or ranked) 2 on the list The Greatest Guilty Pleasure Romantic Comedies
Alicia Silverstone, Brittany Murphy, Paul Rudd

Released: 1995

Directed by: Amy Heckerling

Clueless is a 1995 American comedy film loosely based on Jane Austen's 1815 novel Emma. It stars Alicia Silverstone, Stacey Dash, Paul Rudd, and Brittany Murphy. The film is set in Beverly Hills ...more

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The Best Outfits from Clueless #125 of 1,646 The Most Rewatchable Movies #108 of 923 The All-Time Greatest Comedy Films

3
Crazy, Stupid, Love. is listed (or ranked) 3 on the list The Greatest Guilty Pleasure Romantic Comedies
Emma Stone, Julianne Moore, Ryan Gosling

Released: 2011

Directed by: John Requa, Glenn Ficarra

Crazy, Stupid, Love is a 2011 American romantic comedy-drama film directed by Glenn Ficarra and John Requa, and written by Dan Fogelman. It stars Steve Carell, Ryan Gosling, Julianne Moore, Emma ...more

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4
Love Actually is listed (or ranked) 4 on the list The Greatest Guilty Pleasure Romantic Comedies
Keira Knightley, Elisha Cuthbert, Liam Neeson

Released: 2003

Directed by: Richard Curtis

Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by Richard Curtis. The screenplay delves into different aspects of love as shown through ten separate ...more

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#386 of 1,646 The Most Rewatchable Movies #6 of 114 The Greatest Date Movies of All Time #25 of 693 The Greatest Chick Flicks Ever Made

5
How to Lose a Guy in 10 ... is listed (or ranked) 5 on the list The Greatest Guilty Pleasure Romantic Comedies
Kate Hudson, Matthew McConaughey, Bebe Neuwirth

Released: 2003

Directed by: Donald Petrie

How to Lose a Guy in 10 Days is a 2003 American romantic comedy film directed by Donald Petrie. An advice columnist (Kate Hudson) and an advertising executive (Matthew McConaughey) find ...more

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#276 of 1,646 The Most Rewatchable Movies #18 of 114 The Greatest Date Movies of All Time #543 of 923 The All-Time Greatest Comedy Films

6
Bridget Jones's Diary is listed (or ranked) 6 on the list The Greatest Guilty Pleasure Romantic Comedies
Renée Zellweger, Hugh Grant, Colin Firth

Released: 2001

Directed by: Sharon Maguire

Bridget Jones's Diary is a 2001 British romantic comedy film directed by Sharon Maguire. It is based on Helen Fielding's novel of the same name which is a reinterpretation of Austen's Pride and ...more

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#560 of 1,646 The Most Rewatchable Movies #37 of 114 The Greatest Date Movies of All Time #497 of 923 The All-Time Greatest Comedy Films

7
You've Got Mail is listed (or ranked) 7 on the list The Greatest Guilty Pleasure Romantic Comedies
Tom Hanks, Meg Ryan, Sara Ramirez

Released: 1998

Directed by: Nora Ephron

You've Got Mail is a 1998 American romantic comedy-drama film directed by Nora Ephron, starring Tom Hanks and Meg Ryan. It was written by Nora and Delia Ephron based on the 1937 play Parfumerie ...more

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8
Never Been Kissed is listed (or ranked) 8 on the list The Greatest Guilty Pleasure Romantic Comedies
Jessica Alba, Drew Barrymore, James Franco

Released: 1999

Directed by: Raja Gosnell

Never Been Kissed is a 1999 romantic comedy film produced by 20th Century Fox and Drew Barrymore's production company, Flower Films, directed by Raja Gosnell and starring Drew Barrymore, David ...more

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The Best 'Never Been Kissed' Quotes Will Take You Back To High School #507 of 1,646 The Most Rewatchable Movies #33 of 114 The Greatest Date Movies of All Time

9
50 First Dates is listed (or ranked) 9 on the list The Greatest Guilty Pleasure Romantic Comedies
Drew Barrymore, Adam Sandler, Dan Aykroyd

Released: 2004

Directed by: Peter Segal

50 First Dates is a 2004 American romantic comedy film directed by Peter Segal. Henry Roth (Adam Sandler) has a history of commitment issues until he meets Lucy (Drew Barrymore) who suffers from ...more

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50 First Dates Isn't Romantic - It's About A Guy Who Takes Advantage Of A Disabled Woman #187 of 1,646 The Most Rewatchable Movies #5 of 114 The Greatest Date Movies of All Time

10
While You Were Sleeping ... is listed (or ranked) 10 on the list The Greatest Guilty Pleasure Romantic Comedies
Sandra Bullock, Monica Keena, Bill Pullman

Released: 1995

Directed by: Jon Turteltaub

While You Were Sleeping is a 1995 romantic comedy film directed by Jon Turteltaub and written by Daniel G. Sullivan and Frederic Lebow. It stars Sandra Bullock as Lucy, a Chicago Transit ...more

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11
She's All That is listed (or ranked) 11 on the list The Greatest Guilty Pleasure Romantic Comedies
Sarah Michelle Gellar, Anna Paquin, Lil' Kim

Released: 1999

Directed by: Robert Iscove

She's All That is a 1999 American teen romantic comedy film directed by Robert Iscove and starring Freddie Prinze, Jr. and Rachael Leigh Cook. It is a modern adaptation of George Bernard Shaw's ...more

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#464 of 1,646 The Most Rewatchable Movies #70 of 693 The Greatest Chick Flicks Ever Made #2 of 21 The Most Memorable Prom Dresses In Movies

12
My Best Friend's Wedding... is listed (or ranked) 12 on the list The Greatest Guilty Pleasure Romantic Comedies
Julia Roberts, Dermot Mulroney, Rupert Everett

Released: 1997

Directed by: P. J. Hogan

My Best Friend's Wedding is a 1997 American romantic comedy film directed by P.J. Hogan. When a woman's long-time friend (Dermot Mulroney) reveals he's engaged, she (Julia Roberts) realizes she ...more

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My Best Friend's Wedding Is The Most Twisted, Screwed Up Rom-Com Ever Made #510 of 1,646 The Most Rewatchable Movies #21 of 114 The Greatest Date Movies of All Time

13
Sweet Home Alabama is listed (or ranked) 13 on the list The Greatest Guilty Pleasure Romantic Comedies
Reese Witherspoon, Matthew McConaughey, Dakota Fanning

Released: 2002

Directed by: Andy Tennant

Sweet Home Alabama is a 2002 American romantic comedy film directed by Andy Tennant. A young New York City fashion designer (Reese Witherspoon) finds herself running home to divorce her high ...more

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#309 of 1,646 The Most Rewatchable Movies #24 of 114 The Greatest Date Movies of All Time #13 of 693 The Greatest Chick Flicks Ever Made

14
Notting Hill is listed (or ranked) 14 on the list The Greatest Guilty Pleasure Romantic Comedies
Julia Roberts, Alec Baldwin, Mischa Barton

Released: 1999

Directed by: Roger Michell

Notting Hill is a 1999 British romantic comedy film set in Notting Hill, London, released on 21 May 1999. The screenplay was by Richard Curtis and the film was produced by Duncan Kenworthy and ...more

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15
Runaway Bride is listed (or ranked) 15 on the list The Greatest Guilty Pleasure Romantic Comedies
Julia Roberts, Richard Gere, Christopher Meloni

Released: 1999

Directed by: Garry Marshall

Runaway Bride is a 1999 American romantic comedy film directed by Garry Marshall, and stars Julia Roberts and Richard Gere.The screenplay was written by Josann McGibbon, Sara Parriott and Audrey ...more

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16
Yesterday is listed (or ranked) 16 on the list The Greatest Guilty Pleasure Romantic Comedies
Himesh Patel, Lily James, Kate McKinnon

Released: 2019

Directed by: Danny Boyle

Yesterday is a 2019 British musical comedy film directed by Danny Boyle. A struggling musician, Jack Malik (Himesh Patel), discovers that the whole world has forgotten who the Beatles are and ...more

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17
Sleepless in Seattle is listed (or ranked) 17 on the list The Greatest Guilty Pleasure Romantic Comedies
Tom Hanks, Meg Ryan, Rosie O'Donnell

Released: 1993

Directed by: Nora Ephron

Sleepless in Seattle is a 1993 American romantic comedy-drama film directed and co-written by Nora Ephron. Based on a story by Jeff Arch, it stars Tom Hanks as Sam Baldwin and Meg Ryan as Annie

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18
Kate & Leopold is listed (or ranked) 18 on the list The Greatest Guilty Pleasure Romantic Comedies
Hugh Jackman, Meg Ryan, Liev Schreiber

Released: 2001

Directed by: James Mangold

Kate & Leopold is a 2001 romantic-comedy fantasy that tells a story of a duke who travels through time from New York in 1876 to the present and falls in love with a woman in modern New York. ...more

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19
27 Dresses is listed (or ranked) 19 on the list The Greatest Guilty Pleasure Romantic Comedies
Katherine Heigl, Malin Åkerman, Krysten Ritter

Released: 2008

Directed by: Anne Fletcher

27 Dresses is a 2008 romantic comedy film directed by Anne Fletcher and written by Aline Brosh McKenna. The film stars Katherine Heigl and James Marsden. The film was released January 10, 2008 ...more

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20
About a Boy is listed (or ranked) 20 on the list The Greatest Guilty Pleasure Romantic Comedies
Rachel Weisz, Hugh Grant, Toni Collette

Released: 2002

Directed by: Chris Weitz, Paul Weitz

About a Boy is a 2002 British-American comedy-drama film co-written and directed by brothers Chris Weitz and Paul Weitz. It is an adaptation of the 1998 novel of the same name by Nick Hornby. ...more

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21
Monster-in-Law is listed (or ranked) 21 on the list The Greatest Guilty Pleasure Romantic Comedies
Jennifer Lopez, Jane Fonda, Wanda Sykes

Released: 2005

Directed by: Robert Luketic

Monster-in-Law is a 2005 romantic comedy film directed by Robert Luketic and starring Jennifer Lopez, Jane Fonda, Michael Vartan and Wanda Sykes. It marks a return to cinema for Fonda, being her ...more

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22
High Fidelity is listed (or ranked) 22 on the list The Greatest Guilty Pleasure Romantic Comedies
Catherine Zeta-Jones, Bruce Springsteen, Jack Black

Released: 2000

Directed by: Stephen Frears

High Fidelity is a 2000 American comedy-drama film directed by Stephen Frears and starring John Cusack and Iben Hjejle. The film is based on the 1995 British novel of the same name by Nick ...more

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23
Knocked Up is listed (or ranked) 23 on the list The Greatest Guilty Pleasure Romantic Comedies
Jessica Alba, Eva Mendes, Katherine Heigl

Released: 2007

Directed by: Judd Apatow

Knocked Up is a 2007 American romantic comedy film co-produced, written, and directed by Judd Apatow. The films stars Seth Rogen, Katherine Heigl, Paul Rudd, and Leslie Mann. It follows the ...more

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24
Just Go With It is listed (or ranked) 24 on the list The Greatest Guilty Pleasure Romantic Comedies
Jennifer Aniston, Nicole Kidman, Brooklyn Decker

Released: 2011

Directed by: Dennis Dugan

Just Go with It is a 2011 American romantic comedy film directed by Dennis Dugan, and produced by Adam Sandler, who also starred in the film. The film co-stars Jennifer Aniston, Nicole Kidman, ...more

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#569 of 1,646 The Most Rewatchable Movies #684 of 923 The All-Time Greatest Comedy Films #298 of 693 The Greatest Chick Flicks Ever Made

25
Serendipity is listed (or ranked) 25 on the list The Greatest Guilty Pleasure Romantic Comedies
Kate Beckinsale, John Cusack, Bridget Moynahan

Released: 2001

Directed by: Peter Chelsom

Serendipity is a 2001 American romantic comedy film, starring John Cusack and Kate Beckinsale. It was written by Marc Klein and directed by Peter Chelsom. The music score is composed by Alan ...more

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