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Fast Times with Patrick Dempsey

Esquire US

|

March 2023

Whether in front of the camera or driving a race car, the actor makes everything look easy. We talked to the man formerly known as McDreamy about his role in Michael Mann's forthcoming Ferrari movie, embracing stoicism, and becoming an eyewear designer.

- KEVIN SINTUMUANG

Fast Times with Patrick Dempsey

IMAGINE THIS: IN YOUR EARLY 20S, YOU'RE ALREADY ONE OF AMERICA'S biggest heartthrobs. By your late 30s, you are America's biggest heartthrob. Then you decide to try your hand at being a race-car driver and land on the podium at Le Mans, one of the world's most grueling endurance races. Next you become co-owner of a racing team. Now you're 57, still racing a bit, and you just landed a role in Michael Mann's forthcoming Ferrari movie, because, oh yeah, you're still an incredibly handsome actor. That's Patrick Dempsey. We caught up with him from his home in Maine to find out how he keeps his charmed life in balance.

Esquire: Early in your career, after the movie Can't Buy Me Love, you did the thing that I wish most people would do with their first big payday: You bought a sick vintage car-a 1963 Porsche 356 Cabriolet instead of a new one off a lot.

Patrick Dempsey: I didn't see a lot of exotic cars growing up. Every now and then, you'd see stuff in Maine in the summertime. It wasn't until I got to L. A. that I was absolutely blown away: "Oh my God. People actually buy these cars and they're on the road?" I couldn't believe it. I saw the 356 with a FOR SALE sign. It was the best investment I ever made. But I love my Porsche tractor, too. It's got a great sound to it.

ESQ: I didn't know Porsche made tractors! And now you're collaborating with Porsche Design on glasses. Let's talk about that.

MEER VERHALEN VAN Esquire US

Esquire US

Esquire US

What I've Learned

Marc Maron Podcaster, comedian, writer, actor; 62; Los Angeles

time to read

3 mins

October/November 2025

Esquire US

Esquire US

THE MAN BEHIND THE CURTAIN

His movie adaptation of Wicked earned a gazillion dollars at the box office last year. With a much-hyped sequel set to hit theaters this fall, director Jon M. Chu may be the busiest—and boldest—man in Hollywood.

time to read

5 mins

October/November 2025

Esquire US

Esquire US

A Bag Made for the Journey

BERLUTI'S new PÉRIPLE is soft, sturdy, and something you'll want to reach for EVERY TIME you need to get away for a while

time to read

2 mins

October/November 2025

Esquire US

Esquire US

A RURAL HEALTH-CARE CRISIS IS LOOMING

President Trump's One Big Beautiful Bill slashes Medicaid budgets to shrink Obamacare and fund tax cuts for the wealthy. Now dozens of hospitals in nonurban locations across America may shut down. And the human cost could be incalculable.

time to read

6 mins

October/November 2025

Esquire US

Esquire US

WHAT'S EATING GEORGE CLOONEY?

He's having a career for the ages. He has two adorable kids, a brilliant and beautiful wife, a great new movie, and still has his hair. He enjoys power and influence and is loved by millions, and today he's relaxing at his gorgeous Italian lake house. There's just one problem.

time to read

26 mins

October/November 2025

Esquire US

Esquire US

Time to Shine

Tool watches have had their moment. Now we're GETTING FANCY. These eight TIMEPIECES deliver unmatched SOPHISTICATION and style.

time to read

3 mins

October/November 2025

Esquire US

Esquire US

Getting the Souvenir T-Shirt

YOU KNOW THE ONES WE'RE TALKING ABOUT.

time to read

2 mins

October/November 2025

Esquire US

Esquire US

WHAT IT FEELS LIKE...

Some feats seem unachievable. Climbing Everest in mere days. Kayaking solo across the ocean. Scaling a skyscraper with your bare hands. Few ever face such challenges. Fewer still embrace them with wideopen arms. You're about to read their stories, in their own words-of fear, hope, failure, and triumph, but always passion. This is what it feels like to experience life at its most extraordinary.

time to read

16 mins

October/November 2025

Esquire US

Esquire US

IS ICE A TERRORIST ORGANIZATION?

The question of who in the United States feels safest and for how long—and why—has become the dominant question governing life in this country

time to read

5 mins

October/November 2025

Esquire US

COUNT ME IN

Zegna's II Conte jacket is a surprisingly modern lesson in old-school style

time to read

1 mins

October/November 2025

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