Random Rom-Com Co-Stars You Totally Forgot Were In Other Movies Togeth (11 items)

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  (#10) La La Land

  • Ryan Gosling, Emma Stone, John Legend, Rosemarie DeWitt

  While they are best known for their collaboration in the 2017 Golden Globe-winning film La La Land, Emma Stone and Ryan Gosling play love interests in the romantic comedy, Crazy, Stupid, Love. While the focus of Crazy, Stupid, Love is Steve Carell's personal journey, Stone and Gosling's romance adds a fun twist to the plot. Fans of the duo also got to see them team up in the 2013 mob drama, Gangster Squad.
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  (#4) Chasing Amy

  • Ben Affleck, Matt Damon, Kevin Smith, Casey Affleck, Jason Lee, Joey Lauren Adams, Jason Mewes, Illeana Douglas, Ethan Suplee, Guinevere Turner, Joe Quesada, Scott Mosier, Brian O'Halloran, Walt Flanagan, Brian Lynch, Jeff Anderson, Dwight Ewell, Welker White, Carmen Llywelyn, Mike Allred, Vincent Pereira, Virginia Smith, Ernest O'Donnell, Kelli Simpkins, Robert Hawk, Kristin Mosier, Jeff Millstein, Tse-Mach Washington, Brian Jude, 'Krazy Joe' Fiore, Alexander Goebbel, Tony Torn, John Willyung, Rebecca Waxman, Paris Petrick

  Anyone who had a pulse during the '90s remembers Joey Lauren Adams. One of her first notable appearances came when she played Simone in the cult-classic Dazed and Confused. In the film, her unique look and rad personality is matched only by her co-star, the paddle-wielding, Ben Affleck.

  In 1997, Kevin Smith cast the two in his alt '90s love story, Chasing Amy. Adams and Affleck play Alyssa and Holden, two comic book artists who come together for a brief, star-crossed romance. Adams and Affleck also starred in a few other Kevin Smith films together, most notably, Mallrats and Jay and Silent Bob Strike Back.
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  (#2) The Wedding Singer

  • Drew Barrymore, Adam Sandler, Steve Buscemi, William Michael Albert Broad, Christine Taylor, Jon Lovitz, Kevin Nealon, Brian Posehn, Shanna Moakler, Robert Smigel, Alexis Arquette, Angela Featherstone, Ellen Dow, Frank Sivero, Steven Brill, Peter Dante, Christina Pickles, Allen Covert, Richard Dunn, Carmen Filpi, Tim Herlihy, Dan Lemieux, Maree Cheatham, Matthew Glave, Angela Paton, Michael Shuman, Mark Lonow, Andrew Shaifer, Jenna Byrne, Earl Carroll, Jodi Thelen, Mark Beltzman, Gemini Barnett, Teddy Castellucci, Zachary David Cope, Patrick McTavish, Chauntal Lewis, Priscilla Cory, Joshua Oppenheimer, Jason Cottle, Jon Rosenberg, Jimmy Karz, Todd Hurst, Phyllis Alia, Christopher Alan, Billy Elmer, Sid Newman, Al Hopson, Al Burke, Gabe Veltri, Robert Hackl, Jack Nisbet, Mike Thompson, John Vana, Paul Thiele, Kimberly Schwartz, Sanetta Y. Gipson, John Sawoski, Sally Pierce, Jackie R. Challet, Marnie Schneider, David Sean Robinson, Matthew Kimble, Randy Razz, Michael Jay

  In 1998, Adam Sandler joined forces with Drew Barrymore in The Wedding Singer. The two clicked on-screen, which prompted them to team up again for the 2004 film, 50 First Dates. Their second cinematic outing caught the attention of both hopeless romantics and Sandler fans, in part due to its equal balance of sweetness and ridiculousness. 

  After a decade apart, the duo did it again in 2014 when they starred in the film Blended, in which two families come together. Once again, Sandler's buffoonery combines with Barrymore's charm for a film that blends affectionate, romantic comedy with slapstick absurdity.
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  (#6) Diane Keaton And Jack Nicholson

  Diane Keaton and Jack Nicholson first appeared together in the 1981 film Reds, wherein Keaton's character has an affair with Nicholson's character. 22 years later, they teamed up again for Something's Gotta Give, a romantic comedy about a former playboy who falls for Keaton, despite her actually being his age. 

  While Nicholson's character almost reverts back to his sleazy ways, the time he spends with Keaton's character makes him realize that he wants to settle down and find someone to spend the rest of his life with. 
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  (#1) Paul Rudd and Reese Witherspoon

  In the movie How Do You Know, Paul Rudd and Reese Witherspoon meet at a time when both are dealing with great disappointment. Neither character has much success in love, and their relationships with their significant others feels uncomfortably dormant. In the end, Rudd and Witherspoon hit it off, and it's implied they end up together. 

  While How Do You Know ended up being the duo's last romantic foray, both went on to star in the 2009 animated movie, Monsters vs. Aliens. Additionally, the pair got their start as an on-screen couple in the late-'90s film, Overnight Delivery. 
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  (#9) How to Lose a Guy in 10 Days

  • Kate Hudson, Matthew McConaughey, Bebe Neuwirth, Marvin Hamlisch, Kathryn Hahn, Shalom Harlow, Michael Michele, Thomas Lennon, Robert Klein, Adam Goldberg, Annie Parisse, Marv Albert, Celia Weston, Natalie Madison-Brown, Tony Longo, Georgia Craig, William Duell, Ingrid Hart, Liliane Montevecchi, James Murtaugh, Warner Wolf, Justin Peroff, John DiResta, William Hill, Radio Man, Andrew Moodie, David Macniven, David C. Roehm Sr., Diego Fuentes, Julie McLeod, James Mainprize, Al Bernstein, Doug Murray, Gina Sorell, Samantha Quan, Jeff Gruich, Scott Benes, Zachary Benes, Rebecca Harris, Ross Gallo, Collin Barrett, Jody Raymond, Gery Soles, Bob Reeves, Rod MacDonald, Frank Penny, Bruce Farquhar, Jim Paris, Ames Adamson, Archie MacGregor, Randy Kerdoon

  Almost everyone remembers the 2003 romantic comedy How to Lose a Guy in 10 Days. In the film, Matthew McConaughey and Kate Hudson play career-focused romantics; Hudson's character is writing an article that details ways to quickly lose a guy, and McConaughey's character is on the hunt to prove that he can make any woman fall in love with him.

  In the 2008 film Fool's Gold, the duo reunites. This time, the story follows a recently divorced couple who rekindle their relationship while searching for buried treasure. While Fool's Gold didn't get the same warm reception that How to Lose a Guy in 10 Days received, the movie still exemplifies McConaughey's hapless charm butting heads with Hudson's reserved grace. 

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