Adam Sandler Romantic Comedy Roles

Updated September 22, 2019 47.1k views 9 items

This is a list of romantic comedy movies/films with performances by Adam Sandler, listed alphabetically with movie trailers when available. These Adam Sandler romantic comedy roles include starring, supporting and cameo appearances. You can sort these Adam Sandler romantic comedy movies for additional information as well, such as who directed the films and when they were released.

Over the years, Adam Sandler 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. This list is made up of a variety of Adam Sandler movies, including The Wedding Singer and Mr Deeds. If you enjoy this list, you should also check out this list of Matthew McConaughey romantic comedies.

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. (9 items)
Data-driven recommendations based on voting from over 40 million monthly visits to Ranker. Try the free app
Ranker Video
Video: YouTube

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 amnesiac, along with Rob Schneider, Sean Astin, Lusia Strus, Blake Clark, and Dan Aykroyd. Most of the film was shot on location in Oahu, Hawaii on the Windward side and the North Shore. Sandler and Barrymore won an MTV award. The fictitious memory impairment suffered by Barrymore's character, Goldfield's Syndrome, is similar to short term memory loss and Anterograde amnesia. There is a 2014 Malayalam movie titled Ormayundo Ee Mukham which is inspired by this movie. ...more on Wikipedia

Actors: Drew Barrymore, Adam Sandler, Dan Aykroyd, Rob Schneider, Maya Rudolph, + more

Released: 2004

Directed by: Peter Segal

More 50 First Dates 

50 First Dates Isn't Romantic - It's About A Guy Who Takes Advantage Of A Disabled Woman #57 of 624 The Greatest Guilty Pleasure Movies #186 of 1,699 The Most Rewatchable Movies

Ranker Video
Video: YouTube

Billy Madison is a 1995 American family comedy film directed by Tamra Davis. It stars Adam Sandler in the title role, along with Bradley Whitford, Bridgette Wilson, Norm Macdonald, and Darren McGavin. The film was written by Sandler and Tim Herlihy, and produced by Robert Simonds. It made over $26.4 million worldwide and debuted at number one. The film is about a mentally challenged man who must go back to school in order to take over his father's company. Sandler would later form a production company, Happy Madison Productions, named after a combination of this film's title character and Happy Gilmore's. ...more on Wikipedia

Actors: Adam Sandler, Steve Buscemi, Chris Farley, Norm Macdonald, Bridgette Wilson, + more

Released: 1995

Directed by: Tamra Davis

More Billy Madison 

#12 of 493 The Funniest '90s Movies #241 of 1,699 The Most Rewatchable Movies #164 of 1,030 The All-Time Greatest Comedy Films

Ranker Video
Video: YouTube

I Now Pronounce You Chuck & Larry is a 2007 American comedy film directed by Dennis Dugan, written by Barry Fanaro, and starring Adam Sandler and Kevin James as the title characters Chuck and Larry, respectively. The film was released on July 20, 2007, in the United States; August 16, 2007, in Australia; and on September 21, 2007, in the United Kingdom and Ireland. Although the film received negative reviews by critics for its very crude humor and portrayal of gay people, it was a financial success, ranking #1 at the box office. The film is Sandler's first to be released by Universal Studios since Bulletproof in 1996. ...more on Wikipedia

Actors: Jessica Biel, Adam Sandler, John Goodman, Steve Buscemi, Tila Tequila, + more

Released: 2007

Directed by: Dennis Dugan

More I Now Pronounce You Chuck and Larry 

#466 of 1,699 The Most Rewatchable Movies #752 of 1,030 The All-Time Greatest Comedy Films #14 of 57 The Best and Worst of Adam Sandler

Ranker Video
Video: YouTube

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, Nick Swardson and Brooklyn Decker. The film is based on the 1969 film Cactus Flower, which was adapted from an earlier Broadway stage play written by Abe Burrows, which in turn was based upon the French play Fleur de cactus. Production of the film began on March 2, 2010. The film was released on February 11, 2011 by Columbia Pictures in North America. But despite receiving poor critical reviews, was a box office success by grossing over $214 million. ...more on Wikipedia

Actors: Jennifer Aniston, Nicole Kidman, Brooklyn Decker, Adam Sandler, Minka Kelly, + more

Released: 2011

Directed by: Dennis Dugan

More Just Go With It 

#570 of 1,699 The Most Rewatchable Movies #675 of 1,030 The All-Time Greatest Comedy Films #291 of 804 The Greatest Chick Flicks Ever Made