In his breakout performance, future Grey's Anatomy heartthrob Patrick Dempsey played a high school geek—hello, McNerdy!—who pays a popular girl $1,000 a month to pretend to be his girlfriend. Alas, they somehow end up riding off into the sunset on a lawnmower and his performance was so earnestly charming that it earned him Best Actor in a Motion Picture—Comedy at the 1987 Young Artist Awards.
In Dempsey's follow-up to Can't Buy Me Love, he starred as a pizza delivery boy who becomes a paid escort for his middle-aged clients, played by Kirstie Alley and the late Carrie Fisher. Audiences failed to fall in love with the 1989 comedy, which made just $3 million at the box office.
Apologies to Skeet Ulrich and condolences to Jerry O'Connell, but Dempsey's homicide detective Mark Kinkaid was, and is, our favorite love interest for Sydney Prescott (Neve Campbell). While some fans might've been convinced he was shady, 2022's Scream revealed Sydney married Mark and they have twins, so he really did land the final girl in the end.
Honestly, we still think Dempsey deserved a Best Supporting Actor nomination at the Oscars for his simple-yet-effective line reading of the iconic name "Melanie Smooter." While his character, Andrew Hennings (a.k.a. the son of New York City's mayor) was a total babe in this 2002 Reese Witherspoon-led rom-com, he proved to be no match for Josh Lucas' southern sweetheart.
Who needs a Disney prince when you have Dempsey? That was basically the moral of the story in this beloved 2007 rom-com, which starred Amy Adams as a fairy tale princess who travels to the real world and falls for a single father. And their happily ever after is set to continue when the sequel, Disenchanted, premieres this Thanksgiving on Disney+.
C'mon, like you would actually be able to marry someone else if Mc-Frickin-Dreamy was telling you he was in love with you?! While we love the gender-flipped take on My Best Friend's Wedding, our favorite thing about this 2008 flick is that Kevin McKidd, a.k.a. Dr. Owen Hunt on Grey's, plays the dumped groom. Awkward!
In the third Transformers movie—which grossed $1.1 billion worldwide, NBD!—Dempsey played Dylan Gould, a car collector who was secretly working with the Decepticons. Sure, it's not the franchise's best outing, but it was a blast watching one of TV's most beloved actors break bad and have so much fun doing it.
Going up against rom-com heavyweights like Hugh Grant and Colin Firth is no easy feat. But Dempsey proved to be more than up for the challenge in the 2016 rom-com in which he played charming mathematician Jack Qwant.