Patrick Dempsey Turns 50: How He Went From Totally Geek to Totally Chic

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Over the years, Patrick Dempsey has transformed from being just another cute but dorky star of ’80s teen movies to a hunky leading man. The words that were said about his character in the classic teen flick Can’t Buy Me Love — “I mean, he went from totally geek to totally chic!” — seem to apply as much to Dempsey himself as they did to his character.

On his 50th birthday, here’s a recap of how he did it:

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(Photos: Getty Images)

He learned to tame his amazing curly locks

Most of the human race had hairstyles as embarrassing as they were big in the ’80s, and Dempsey was no exception. (Please check out the aforementioned Can’t Buy Me Love as well as Loverboy.) But Dempsey’s was really bad back in the day, and when he returned for his unofficial second act, with a role in Scream 3 and a guest part in the sitcom Will and Grace in 2000, it was really good. In fact, Dempsey’s hair grew quite a following of its own.

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(Photo: WireImage)

He simply outgrew the geekiness

When a more mature Dempsey began to pop up in high-profile projects again in the ’00s, it wasn’t just his hair that had changed. He was somehow different and had a new confidence about him. Dempsey explained the transition in a 2006 interview with Details, saying that he was so bitter about his career, the flops, and the inability to get considered for good roles that he no longer cared.

“He’s not trying too hard,” his Grey’s Anatomy co-star Ellen Pompeo said. “He’s sexier because he’s not chasing anything anymore. It’s a law of physics — when you run after something, it runs away from you.”

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(Photo: AP)

His good deeds made him all the more attractive

The Demps did something beautiful, more beautiful than even his tresses, when he founded the Patrick Dempsey Center for Cancer Hope & Healing to provide free support groups, nutrition counseling, yoga, and other services to people affected by cancer. Started in 2008 in the actor’s hometown of Lewiston, Maine, the center was inspired by Dempsey’s mother, Amanda Dempsey, who died in April 2014 after struggling with ovarian cancer for 17 years. Dempsey regularly participates in events, such as the 2010 bike ride pictured above, to benefit it.

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(Photo: Getty Images)

He got some cool wheels

That never hurts, right? Dempsey found a passion in auto racing after his wife, Jillian Fink, gave the lifelong car fanatic driving lessons as a gift in 2004. Eleven years later, Dempsey came in second place at France’s annual 24 Hours of Le Mans race, which dates back to 1923.

In 2014, Dempsey went as far as telling the New York Times that he prefers the diver’s seat to a Hollywood set.

“There’s something very satisfying about training,” he said. “Psychologically and emotionally, the process and the inner desire that it takes and the mental focus it takes to be competitive is far more satisfying to me in many ways than acting.”

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(Photo: Getty Images)

He went ‘Grey’

Yes, we’re talking about Dempsey’s famous mane, but we’re also referring to Grey’s Anatomy, the primetime soap starring none other than Dempsey that became a huge hit after its 2005 debut. As Dr. McDreamy, the on-again, off-again love of Dr. Meredith Grey, Dempsey left viewers swooning.

People named him one of the Sexiest Men Alive in 2008, which he found baffling. “This is so funny,” he told the magazine. “I’m a hunky guy now. How did that happen?’

Dempsey was killed off Grey’s after 11 seasons on the show in 2015, reportedly either because of an affair with an intern, a feud with creator Shonda Rhimes, or his own boredom, but he’ll forever be remembered as McDreamy anyway.