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Patrick Dempsey arrives for the 20th GQ Men of the Year Award in 2018

Patrick Dempsey looks unrecognizable in shocking throwback photo you don't want to miss

The 57-year-old Grey's Anatomy actor once sported a very difficult look 

Hannah Hargrave
US Deputy Editor
November 8, 2023
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Patrick Dempsey was stunned to learn he'd earned the title of People's 2023 Sexiest Man Alive but he's reveling in the heartthrob status. 

It's hard to believe that it has been almost 20 years since he took on the role as Derek 'McDreamy' Shepherd in Grey's Anatomy, but he's been a household name for a lot longer. 

While his chiseled good looks, and salt and pepper hair have landed him his latest crown, at the beginning of his career, he looked a lot different. 

WATCH: Patrick Dempsey shaves off his hair - see the results

Patrick was only 16 years old when he played Mike Damone in the Fast Times at Ridgemont High spin-off, Fast Times.

With his curly mop of hair, and boyish charm, Patrick oozed confidence. The handsome stubble he often sports today, was only just making an appearance in the teen photos.

Patrick Dempsey as a teenager in Fast Times, a spin-off of Fast Times at Ridgemont High
Patrick Dempsey as a teenager in Fast Times, a spin-off of Fast Times at Ridgemont High

From that short-lived role, 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.

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
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, but confessed that it wasn't something he was expecting. 

Patrick Dempsey in 1989 sporting big, bold hair
Patrick Dempsey in 1989 sporting big, bold hair

Now though, he wants 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."

He is the proud founder of the Dempsey Center, which honors his late mom who died from cancer and aims to support patients and their loved ones. 

Patrick Dempsey as Derek Shephard in Grey's© Getty
Patrick Dempsey left the show in 2015, but made a brief cameo in 2021

Patrick is also a devoted family man and shares his two children, Talula, 21, and 16-year-old twins, Sullivan and Darby, with his makeup artist wife, Jillian, 57.

When he received the news of his title, he couldn't believe it. "I was completely shocked," he said. "And then I started laughing, like, this is a joke, right? I’ve always been the bridesmaid.

jillian patrick dempsey© Photo: Getty Images
Patrick with his wife Jillian

"I’d completely forgotten about it and never even contemplated being in this position. So my ego is good."

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