Film Matthew McConaughey Romantic Comedy Roles

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The best of Matthew McConaughey's romanic comedy roles that appear on this list are sweet, funny, and a little bit cheesy - all the makings of a classic rom-com. McConaughey's adorable southern drawl is enough to make any of his onscreen leading ladies melt, and his impeccable comedic timing is sure to bring home the laughs. Whether you're a fan of his determined, game-playing character in How to Lose a Guy in 10 Days, or his stubborn, immature character in Failure to Launch, this list of the best Matthew McConaughey romantic comedies is sure to feature some of your favorites.  

If you've been looking for the answer to the questions, "What Romantic comedy movies has Matthew McConaughey been in?" or "What are the best Matthew McConaughey Romantic comedy roles?" look no further!  

Check out this list of Matthew McConaughey's most iconic romantic comedy roles, and be sure to let us know what you think in the comment section. 
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Actors: Matthew McConaughey, Elizabeth Hurley, Ellen DeGeneres, Bryce Dallas Howard Jay Leno, + more

Initial Release: 1999

Directed by: Ron Howard

Also Ranked

#616 on The Greatest Guilty Pleasure Movies

#3612 on The Best Movies of All Time

#602 on The Absolute Most Hilarious Movies Ever Made

#638 on The Worst Movies Of All Time

see more on EDtv

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Actors: Zooey Deschanel, Sarah Jessica Parker, Matthew McConaughey, Bradley Cooper Terry Bradshaw, + more

Initial Release: 2006

Directed by: Tom Dey

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#286 on The Greatest Guilty Pleasure Movies

#1294 on The Most Rewatchable Movies

#158 on The Greatest Romantic Comedies of All Time

#389 on The Worst Movies Of All Time

see more on Failure to Launch

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Actors: Kate Hudson, Matthew McConaughey, Donald Sutherland, Kevin Hart Ray Winstone, + more

Initial Release: 2008

Directed by: Andy Tennant

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#309 on The Greatest Guilty Pleasure Movies

#155 on The Greatest Romantic Comedies of All Time

#2693 on The Best Movies of All Time

#577 on The Absolute Most Hilarious Movies Ever Made

see more on Fool's Gold

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Actors: Kate Hudson, Matthew McConaughey, Bebe Neuwirth, Marvin Hamlisch Kathryn Hahn, + more

Initial Release: 2003

Directed by: Donald Petrie

Also Ranked

#179 on The Greatest Guilty Pleasure Movies

#446 on The Most Rewatchable Movies

#19 on The Greatest Romantic Comedies of All Time

#27 on The Best Date Movies

see more on How to Lose a Guy in 10 Days

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Actors: Matthew McConaughey, Renée Zellweger, Philip Seymour Hoffman, Cloris Leachman Matthew Fox, + more

Initial Release: 1993

Directed by: Bob Balaban

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#34 on The 20+ Best Matthew McConaughey Movies of All Time

#74 on The Best Movies of 1993

#12 on The Best PG-13 Horror Comedies

#5 on The Best Traci Lind Movies

see more on My Boyfriend's Back

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Actors: Emma Stone, Jennifer Garner, Matthew McConaughey, Lacey Chabert Michael Douglas, + more

Initial Release: 2009

Directed by: Mark Waters

Also Ranked

#455 on The Greatest Guilty Pleasure Movies

#141 on The Greatest Romantic Comedies of All Time

#3987 on The Best Movies of All Time

#13 on The 20+ Best Matthew McConaughey Movies of All Time

see more on Ghosts of Girlfriends Past

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Actors: Jennifer Lopez, Matthew McConaughey, Judy Greer, Bridgette Wilson Justin Chambers, + more

Initial Release: 2001

Directed by: Adam Shankman

Also Ranked

#246 on The Greatest Guilty Pleasure Movies

#795 on The Most Rewatchable Movies

#198 on The Greatest Romantic Comedies of All Time

#7 on The 20+ Best Matthew McConaughey Movies of All Time

see more on The Wedding Planner

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Actors: Kate Beckinsale, Matthew McConaughey, Gary Oldman, Peter Dinklage Patricia Arquette, + more

Initial Release: 2003

Directed by: Matthew Bright

Also Ranked

#683 on The Greatest Guilty Pleasure Movies

#33 on The 20+ Best Matthew McConaughey Movies of All Time

#25 on The Best Kate Beckinsale Movies

#139 on The Most Confusing Movies Ever Made

see more on Tiptoes