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.

PD: We better, because they’ll get mad at me if I don’t! They approached me to do an eyeglass campaign. And then we thought it’d be fun to work on a collection. Something that fits into my lifestyle. So we took inspiration from racing and street cars—there’s a lot of titanium and carbon fiber to reduce weight—and we looked at what we can put under our helmets if we’re out in a car doing a rally. It was like, “How do we make a better mousetrap? How do we make a better pair of glasses?”

patrick dempsey
Carter Smith
Jacket and jeans by Tom Ford; boots by Rancourt & Co.; P’8965 Patrick Dempsey Ltd. Edition sunglasses by Porsche Design.

ESQ: You’re very much a Porsche guy, but you’re in the new movie Ferrari with Adam Driver that Michael Mann is directing. What was that like?

PD: I play Piero Taruffi. He wins the Mille Miglia, the final race. Extraordinary man. He was an engineer and a land-speed-record holder in motorcycle racing. And he’s the old gray fox, so that was the only role I was right for.

We shot racing sequences on the old roads where they actually tested the Ferraris in and around Modena. That was what was so great about working with Michael, because he was like, “You’re going to do all the driving. You’re not going to have a double.” He’s a master filmmaker. Every detail is planned in his head. And sometimes you don’t quite understand it at first. And he’ll direct you in a way that sets you off a little bit from being comfortable. And then once you start to see what he’s going for, you’re like, “Oh my goodness, this is amazing.”

patrick dempsey
Carter Smith
Turtleneck by Brioni; P’8754 Patrick Dempsey Ltd. Edition glasses by Porsche Design.

ESQ: It’s one thing to be obsessed with cars like I am. It’s another thing to race them, which you’ve done very successfully. You made the podium at Le Mans, the famous 24-hour endurance race in France. Do you get even more satisfaction out of racing than you do acting?

PD: Yeah, it’s mentally very cleansing and physically as well, because of the mental focus and meditation of it. It’s really a relationship with yourself. How far can you push yourself to go past things that make you uncomfortable? And can you be comfortable in an uncomfortable situation? That’s what’s satisfying about it.

ESQ: I think a lot of people don’t know that you’ve practiced meditation for decades.

PD: There’s just so much going on in the world, right? You want to get back to chop the wood, carry the water. This becomes your mantra, because there’s so many things that can distract you and give you anxiety. That’s what I try to focus on—to take that away. And I’ve been studying stoicism for about five years now. It started when I was in Rome on [the TV series] Devils, actually. It was really interesting, because I couldn’t fall asleep. I had terrible jet lag. And I’m like, “Why don’t I study Roman history?” And then I came across Marcus Aurelius’ Meditations. I read one book, but I didn’t quite understand it. I kept looking, and then I came across Ryan Holiday’s work, and that really spoke to me. He’s really been able to package Marcus Aurelius’ Meditations in a way that is very applicable to daily life, where you see the results immediately.

ESQ: There’s quite a few actors who pursue racing. Steve McQueen, Paul Newman, more recently Michael Fassbender. What do you think the attraction is with actors and racing?

PD: It’s hard to say what is winning in Hollywood. Is it a big opening weekend? Is it an Oscar? With motorsport, it’s like either you’re the fastest or you’re not. There’s no bullshit. Maybe your car’s a little bit better or tires are this or that. But at the end of the day, it’s just your natural ability. And the times tell you. You know if you’re good or not. Hollywood is abstracted success.