Comedy

The Greatest Guilty Pleasure Romantic Comedies 

Alan Smithee
Updated October 2, 2019 434 votes 51 voters 2k 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! 

list ordered by
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 teen romantic comedy-drama film. It is directed by Gil Junger and stars Julia Stiles, Heath Ledger and Joseph Gordon-Levitt. The romantic comedy ...more

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#6 of 803 The Greatest Chick Flicks Ever Made #302 of 1,196 The Absolute Funniest Movies Of All Time

2
Crazy, Stupid, Love. is listed (or ranked) 2 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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#615 of 1,009 The All-Time Greatest Comedy Films #29 of 172 The Greatest Date Movies of All Time

3
Love Actually is listed (or ranked) 3 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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#221 of 1,699 The Most Rewatchable Movies #92 of 292 The Top Tearjerker Movies That Make Men Cry

4
Clueless is listed (or ranked) 4 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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#120 of 1,699 The Most Rewatchable Movies #10 of 803 The Greatest Chick Flicks Ever Made The Best Outfits from Clueless

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 romantic comedy film, directed by Donald Petrie, starring Kate Hudson and Matthew McConaughey. It is based on a short cartoon book of the same name by ...more

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#525 of 1,009 The All-Time Greatest Comedy Films #697 of 1,196 The Absolute Funniest Movies Of All Time

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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#385 of 1,699 The Most Rewatchable Movies #50 of 803 The Greatest Chick Flicks Ever Made #580 of 1,009 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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#100 of 624 The Greatest Guilty Pleasure Movies #406 of 1,699 The Most Rewatchable Movies #136 of 493 The Funniest '90s Movies

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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#540 of 1,699 The Most Rewatchable Movies #26 of 803 The Greatest Chick Flicks Ever Made #37 of 258 The Best Teen Romance Movies

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 and written by George Wing. The film stars Adam Sandler as a lothario veterinarian and Drew Barrymore as an ...more

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#162 of 1,699 The Most Rewatchable Movies #162 of 1,009 The All-Time Greatest Comedy Films 50 First Dates Isn't Romantic - It's About A Guy Who Takes Advantage Of A Disabled Woman

10
Sweet Home Alabama is listed (or ranked) 10 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, starring Reese Witherspoon, Josh Lucas, Patrick Dempsey and Candice Bergen. The film was released by ...more

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#510 of 1,699 The Most Rewatchable Movies #19 of 803 The Greatest Chick Flicks Ever Made

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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#1,130 of 1,699 The Most Rewatchable Movies #21 of 258 The Best Teen Romance Movies #86 of 94 The Worst January Movie Releases

12
While You Were Sleeping ... is listed (or ranked) 12 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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#94 of 624 The Greatest Guilty Pleasure Movies #57 of 803 The Greatest Chick Flicks Ever Made #143 of 493 The Funniest '90s Movies

13
Runaway Bride is listed (or ranked) 13 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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#92 of 803 The Greatest Chick Flicks Ever Made #884 of 1,196 The Absolute Funniest Movies Of All Timelisted on The Highest Grossing 90s Movies

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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#566 of 1,699 The Most Rewatchable Movies #71 of 302 The Greatest Soundtracks of All Time

15
My Best Friend's Wedding... is listed (or ranked) 15 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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#31 of 803 The Greatest Chick Flicks Ever Made #553 of 1,009 The All-Time Greatest Comedy Films My Best Friend's Wedding Is The Most Twisted, Screwed Up Rom-Com Ever Made

16
Sleepless in Seattle is listed (or ranked) 16 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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#84 of 624 The Greatest Guilty Pleasure Movies #265 of 1,699 The Most Rewatchable Movies #242 of 1,009 The All-Time Greatest Comedy Films

17
Kate & Leopold is listed (or ranked) 17 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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#58 of 74 The Best Movies Released Christmas Day #11 of 23 Great Drama Movies That Play with Time

18
27 Dresses is listed (or ranked) 18 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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#624 of 1,699 The Most Rewatchable Movies #55 of 94 The Worst January Movie Releases #44 of 67 The Greatest Female-Led Comedy Movies

19
About a Boy is listed (or ranked) 19 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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#810 of 1,699 The Most Rewatchable Movies #222 of 410 The Best Rainy Day Movies

20
Monster-in-Law is listed (or ranked) 20 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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#370 of 803 The Greatest Chick Flicks Ever Made #39 of 100 The Most Rewatchable Comedy Movies #3 of 58 The Best Romantic Comedy Movies On Netflix

21
High Fidelity is listed (or ranked) 21 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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#1,021 of 1,699 The Most Rewatchable Movies #27 of 302 The Greatest Soundtracks of All Time

22
Knocked Up is listed (or ranked) 22 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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#523 of 1,699 The Most Rewatchable Movies #202 of 803 The Greatest Chick Flicks Ever Made #112 of 1,009 The All-Time Greatest Comedy Films

23
Just Go With It is listed (or ranked) 23 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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#1,490 of 1,699 The Most Rewatchable Movies #276 of 803 The Greatest Chick Flicks Ever Made #510 of 1,196 The Absolute Funniest Movies Of All Time

24
Serendipity is listed (or ranked) 24 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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#25 of 172 The Greatest Date Movies of All Time #89 of 109 The Best Christmas Movies of All Time #20 of 20 The Greatest Movie Wedding Proposals

25
Amélie is listed (or ranked) 25 on the list The Greatest Guilty Pleasure Romantic Comedies
Audrey Tautou, Spencer Tracy, Joan Bennett

Released: 2001

Directed by: Jean-Pierre Jeunet

Amélie is a 2001 romantic comedy film directed by Jean-Pierre Jeunet. Written by Jeunet with Guillaume Laurant, the film is a whimsical depiction of contemporary Parisian life, set in ...more

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#407 of 1,699 The Most Rewatchable Movies #226 of 803 The Greatest Chick Flicks Ever Made #333 of 1,009 The All-Time Greatest Comedy Films