Patrick Dempsey may be new to the Sexiest Man Alive thing, but he’s been entertaining us since the ’80s.
The 57-year-old actor was asked by People if he’s peaked now that he’s been given the title — previously held by Ryan Reynolds, Dwayne Johnson, Brad Pitt and Chris Evans among others — and he replied with a laugh, “I peaked many years ago. But I’m still here.”
Dempsey, who will appear in next month’s race car flick Ferrari (which has an interim agreement from SAG-AFTRA amid the strike), has been a working actor in Hollywood since he was about 20. He had a starring roles in a series of teen flicks, making him a certified ’80s heartthrob — with great hair even back then. Dempsey — who shares three kids with wife Jillian Fink Dempsey — continued working in the ’90s but then really blew up again in the aughts. McDreamy, anyone?
Here are some of his most memorable roles.
Can’t Buy Me Love (1987)
Dempsey’s character went from geek to chic in the high school rom-com. Ronald Miller used all the money he earned mowing lawns to pay the most popular girl in school to make him cool. It worked — for a minute. While his popularity waned, he ended up riding off into the sunset with the girl set to an iconic Beatles song. So what if he was driving a lawn mower?!
Loverboy (1989)
He graduated to college hunk for this comedy, which co-starred Kirstie Alley and Carrie Fisher. In what seems like such an ’80s kinda film, his character, Randy, was slacking at college so his dad made him come home and get a job. Delivering pizzas at Señor Pizza wasn’t a dream gig … but it became more lucrative when older, married women starting requesting special deliveries. “Extra anchovies” turned into an escort business, which — as you’d guess — didn’t end up great for poor Randy. But he did get to return to college.
Once & Again (2000 to 2002)
Dempsey crossed over to TV in the ’90s, including playing the future president in the JFK: Reckless Youth and the main character in the Kennedy-esque A Season in Purgatory. After a multi-episode arch on Will & Grace (as Will’s closeted sportscaster BF), he had an even more memorable turn doing four episodes of Once & Again, which landed him an Emmy nomination in 2001 for Outstanding Guest Actor in a Drama Series. He played Aaron, brother of series star Sela Ward’s character, who had schizophrenia.
Sweet Home Alabama (2002)
Dempsey later played Andrew, the richy rich fiancé of Reese Witherspoon’s character, Melanie in this mega hit rom-com. His charm couldn’t match that of Josh Lucas’s Southern comfort, but the dapper New Yorker landed on his feet.
Grey’s Anatomy (2005 to 2021)
Meredith (Ellen Pompeo) wasn’t the only one smitten with Dr. Derek Shepherd with the good hair. Fans have referred to Dempsey as “McDreamy” IRL for years, even after he exited the role, popping back in for ghostly visits from time to time.
Enchanted (2007) and Disenchanted (2022)
In the Disney flick, the widower played a modern-day prince charming after Amy Adam’s Giselle arrived in NYC. They fell in love in the romcom and became a happy family with his daughter. The sequel 15 years later brought them back together for more fantasy hijinks — and of course a happily ever after ending.
Now, we’ll leave you with one role Dempsey tried to play: a Yahoo correspondent. Watch his funny red carpet moment in 2022:
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