Patrick Dempsey Romantic Comedy Roles

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List of Romantic comedy movies/films with performances by Patrick Dempsey, listed alphabetically with movie trailers when available. These Patrick Dempsey Romantic comedy roles include starring, supporting and cameo appearances. You can sort these Patrick Dempsey Romantic comedy movies for additional information as well, such as who directed the films and when they were released. Over the years Patrick Dempsey has become known for playing characters in Romantic comedy movies, so this list is the perfect resource for finding some you haven't already seen.

These movies, like Valentine's Day and Sweet Home Alabama include images when available.

This list answers the questions, "What Romantic comedy movies has Patrick Dempsey been in?" and "What are the best Patrick Dempsey Romantic comedy roles?"

You can't vote on this list, but if you want to re-order it you can re-rank the list to put your favorites at the top. (13 items)
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Can't Buy Me Love is a 1987 teen comedy feature film starring Patrick Dempsey and Amanda Peterson in a story about a nerd at a high school in Tucson, Arizona who gives a cheerleader $1,000 to pretend to be his girlfriend for a month. The film was directed by Steve Rash and takes its namesake from a Beatles song of the same name. ...more on Wikipedia

Actors: Paula Abdul, Patrick Dempsey, Seth Green, Amanda Peterson, Brandi Brandt, + more

Released: 1987

Directed by: Steve Rash

More Can't Buy Me Love

#88 of 443 on The Funniest '80s Movies #59 of 284 on The Best Teen Romance Movies #19 of 50 on 50 Movies That Contained Future Stars #30 of 66 on The Best Movies About Getting Dumped

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Denial is a 1998 film written and directed by Adam Rifkin. It was released to video under the title Something About Sex. The plot revolved around couples as they struggle with the hardships of maintaining a monogamous relationship. It starred Jonathan Silverman, Leah Lail, Patrick Dempsey, Christine Taylor, Ryan Alosio, Amy Yasbeck, and Jason Alexander. It was produced by Brad Wyman. ...more on Wikipedia

Actors: Patrick Dempsey, Angie Everhart, Christine Taylor, Jason Alexander, Maria Bamford, + more

Released: 1998

Directed by: Adam Rifkin

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#87 of 89 on The Best Courtroom Drama Movies #33 of 43 on The Best Patrick Dempsey Movies

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Enchanted is a 2007 American musical live-action/animated fantasy romantic comedy film, produced by Walt Disney Pictures with New York Academy Barry Sonnenfeld and Josephson Entertainment. Written by Bill Kelly and directed by Kevin Lima, the film stars Amy Adams, Patrick Dempsey, James Marsden, Timothy Spall, Idina Menzel, Rachel Covey, and Susan Sarandon. The plot focuses on Giselle, an archetypal Disney Princess, who is forced from her traditional animated world of Andalasia into the live-action world of New York City. Enchanted was the first Disney film to be distributed by Walt Disney Studios Motion Pictures, instead of Buena Vista Pictures Distribution. The film is both an homage to, ...more on Wikipedia

Actors: Amy Adams, Susan Sarandon, Julie Andrews, Patrick Dempsey, Idina Menzel, + more

Released: 2007

Directed by: Kevin Lima

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#46 of 374 on The Best Musical Movies of All Time #75 of 186 on The Best Movies for Tweens #3 of 136 on The Best Disney Live-Action Movies #60 of 205 on Musical Movies With the Best Songs

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Flypaper is a 2011 crime fiction comedy film written by Jon Lucas and Scott Moore, and directed by Rob Minkoff. ...more on Wikipedia

Actors: Patrick Dempsey, Octavia Spencer, Jeffrey Tambor, Tim Blake Nelson, Matt Ryan, + more

Released: 2011

Directed by: Rob Minkoff

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