Years before Patrick Dempsey earned heartthrob status with his salt and pepper hair and chiseled good looks, he showcased a very different appearance.
The star has earned himself legions of loyal fans from his decades long career in TV and film and was only 16 years old when he played Mike Damone in the Fast Times at Ridgemont Highspin-off, Fast Times.
See what he looked like with a curly mop of hair, and boyish charm, in photos from the start of his career.
Patrick Dempsey as a teenager in Fast Times, a spin-off of Fast Times at Ridgemont High
From that short-lived role on Fast Times, Patrick went on to star in teen romantic comedy Can’t Buy Me Love and played a nerdy outcast, trying to be a cool kid.
Sexiest man alive
In the movie, In the Mood, his character was a hunky teenager who had a passion for older women, and the following year he once again played a cougar in the 1989 flick, Loverboy.
Patrick Dempsey poses for a portrait 1985
While his career had a dip in the 1990s, a decade later he was back with a vengeance, starring in Sweet Home Alabama alongside Reese Witherspoon before the ABC medical drama, Grey’s Anatomy, hit the screens in 2005.
Patrick graciously accepted the People’s Sexiest Man Alive award, in 2023 but confessed that it wasn’t something he was expecting.
Patrick Dempsey in 1989 sporting big, bold hair
Despite the surprise, he said at the time that he planned to to use it for good. “I’m glad it’s happening at this point in my life,” he told the outlet as their cover star.
“It’s nice to have the recognition, and certainly my ego takes a little bump, but it gives me the platform to use it for something positive.”
Patrick said he was “completely shocked,” by the award and initially thought it was a joke. “I’ve always been the bridesmaid,” he quipped.
Patrick Dempsey left the show in 2015, but made a brief cameo in 2021 (Getty)
Family life
Away from his career, Patrick is a devoted family man and shares his three children, Talula, 24, and 19-year-old twins, Sullivan and Darby, with his makeup artist wife, Jillian. He’s admitted it was “very challenging” raising his offspring in Hollywood, but he and Jillian have kept “a good, calm, loving, safe environment for them.”
Patrick with his wife Jillian (Photo: Getty Images)
Patrick revealed that his kids are very “disciplined” and “want to have their own identity,” by creating very different paths from each other.
Talula studied at the famed culinary school Le Cordon Bleu and is now a pastry chef, launching her own business, Talula’s Kitchen.
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Darby and Sullivan graduated from the prestigious Crossroads School for Arts & Sciences in Santa Monica, California, in May 2025.
Darby is currently studying at the University of California, San Diego, while Sullivan now lives in New York City, where he attends New York University Tisch School of the Arts while also studying acting at the renowned Stella Adler Studio of Acting.
See their best family photos below.
patrick dempsey with family at wimbledon
Patrick with his wife and daughter at Wimbledon
Chic
Patrick Dempsey, Jillian Fink at the CHANEL and Charles Finch Pre-Oscar Awards Dinner held at The Polo Lounge on March 01, 2025 in Beverly Hills, California. (Photo by Gilbert Flores/Variety via Getty Images)
They’ve admitted raising in kids in Hollywood is hard
Parenting
Sullivan looks incredible in new photos
Their son Sullivan is breaking into modeling and acting
Fashion foward
Sullivan Dempsey, Talula Dempsey, Patrick Dempsey, Jillian Fink and Darby Dempsey attend the Los Angeles Premiere of Neon’s “Ferrari” at Directors Guild Of America on December 12, 2023 in Los Angeles, California
They’ve all got their own talents
Talented
Jillian and Patrick Dempsey with their children Talula, Sullivan and Darby
Patrick and Jillian are incredibly supportive of their kids
