15 Movies With 'Grey's Anatomy' Actors In Surprising Roles — Including Your Fave '90s Rom-Com

Grey’s Anatomy has been going on for what feels like forever, so it’s easy to forget that many of the show's stars had prolific careers before joining the cast, or were able to find careers in film after graduating from their TV roles on the hit show. There are plenty of movies featuring Grey’s Anatomy cast members in surprising roles, and if you missed the flicks in theaters, go find them now. The Shonda Rhimes show has turned actors like Jesse Williams and Sandra Oh into household names, shifting them from indie darlings to bonafide Hollywood stars. And then there's titular star Ellen Pompeo, who, thanks to Grey's, shifted from small roles to one of the most recognizable names in television.

Don’t be fooled though; just because Pompeo and Patrick Dempsey, for instance, weren’t big names before Grey’s doesn’t mean they didn’t have roles in some huge films before becoming Meredith Grey and Derek Shepherd. Did you know that Pompeo was in Catch Me If You Can? Or that before becoming one of the dreamiest men in television, Dempsey had his first big role playing a nerd who wins over his crush’s love in Can’t Buy Me Love?

With Season 14 underway, now’s the perfect chance to re-watch some of your favorite movies or discover some you might have missed starring your favorite Grey’s stars.

1'Sideways'

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A year before Grey's Anatomy, Sandra Oh received attention for her standout role in the Oscar-winning dark comedy Sideways as Stephanie, a character who is as badass as Cristina Yang.

2'Enchanted'

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Just when you thought McDreamy couldn't possibly become dreamier, he became a Disney prince in Enchanted.

3' Under The Tuscan Sun'

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Before reuniting onscreen on Grey's Anatomy, Sandra Oh and Kate Walsh played a couple in Under the Tuscan Sun. Maybe you'd never imagine Cristina Yang and Addison Montgomery dating, but this pairing makes perfect sense in the movie.

4'Cabin In The Woods'

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Remember Joss Whedon's wacky horror movie Cabin in the Woods? What you might've forgotten is that Grey's Jesse Williams was one of its stars, playing nerdy Holden.

5'The Princess Diaries'

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You've probably watched Princess Diaries a million times already, but you're going to want to watch it again after finding out Oh's in it. Her role was small, but you might remember her scene after she briefly became a meme.

6'Can't Buy Me Love'

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If you've never heard of Can't Buy Me Love, you need to watch one of the most underrated '80s rom-coms. Dempsey stars as a very nerdy high school outcast, Ronald, who comes up with a proposal after he witnesses Cindy, the most popular girl in school, have a glass of wine spilled all over her mom's expensive suede outfit: he'll give her $1000 to buy an identical new outfit in exchange for her to help him look "cool" by pretending to be his girlfriend for a month.

7'Knocked Up'

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Katherine Heigl might be one of the most polarizing former Grey's stars, but her role as Izzie did briefly give her a career as the rom-com queen. This ranged from 27 Dresses to The Ugly Truth, but one of her most unexpected rom-com roles was in Judd Apatow comedy Knocked Up.

8'X-Men: The Last Stand'

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The same year Eric Dane became McSteamy, he also became a Marvel villain. In case you don't remember, Dane played Multiple Man, who is recruited by Magneto and has the power of multiplying himself.

9'Girls Trip'

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Kate Walsh is mostly known for her serious roles, but in Girls Trip she plays the hilarious yet super cringe-worthy role of Ryan's agent, Elizabeth.

10'Catch Me If You Can'

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It's probably been a while since you've watched this iconic Leonardo DiCaprio movie but did you spot Pompeo in it?

11'P.S. I Love You'

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If you've been watching Grey's Anatomy since the beginning, you remember Denny Duquette's (played by Jeffrey Dean Morgan) death being one of the most heartbreaking moments in the show's early days. If you want to experience the sadness all over again, might as well watch P.S. I Love You.

12'Trainspotting'

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Trainspotting is one of those films that appears in practically every list of top best movies of all-time. If you haven't watched it yet, you're going to finally be convinced to do so after learning Kevin McKidd (aka Owen) is in it and its sequel.

13'You've Got Mail'

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Sara Ramírez appears in You've Got Mail, but unfortunately it's in a ridiculously small role as a cashier. Goes to show how much Grey's changed everything for her.

14'Perks Of Being A Wallflower'

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The film adaptation of Perks of Being a Wallflower had a pretty great cast, including Paul Rudd, Emma Watson, Logan Lerman, and Ezra Miller. It's easy to forget Kate Walsh was also in it, playing Charlie's mom.

15'How Stella Got Her Groove Back'

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If you haven't watched this empowering '90s classic yet, you definitely need to check it out. The Chief, aka James Pickens Jr., appears in it alongside a great cast including Angela Bassett, Taye Diggs, and Whoopi Goldberg.

16Honorable Mention: 'Eternal Sunshine Of The Spotless Mind'

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Here's something you probably didn't know: Ellen Pompeo was supposed to have a role in Eternal Sunshine of the Spotless Mind, but ultimately her scene was cut. She plays Joel's girlfriend who he breaks up with to try to recuperate his relationship with Clementine.

If you haven't seen any of these in a while or missed them when they came out, do yourself a favor and get watching.