On a sunny California Wednesday, Patrick Dempsey cruised into our Malibu shoot with undeniable style, effortless charm, and enviable cool. Stepping out of his Porsche Cayenne GTS, he greeted us with a smile and a cheerful wave, the very picture of gentlemanly sophistication. We sat down to chat at the magical ocean-view property, a homey mix of warm-tone wood and sun-flooded rooms that served as the perfect backdrop to our afternoon. Dempsey seemed to fit right in, with an easy grin and a quiet charisma that couldn’t help but brighten everyone’s mood. With the soft music of wind chimes and the guest appearance of two (very welcome!) dogs, we dove into everything Dempsey — his love of cars, balancing a career and family, and the type of person he strives to be.

With the goal of becoming a ski racer, Dempsey never planned on acting. “I didn’t know I wanted to be an actor,” he reminisces; “I fell into it completely by accident. I grew up in a little town called Buckfield, Maine. It was like the hotbed for the new vaudevillian movement, and they recruited me, and that’s how I got the bug of performing.” I ask if he can pinpoint a “big break” moment, and he nods enthusiastically. “When Harvey Fierstein discovered me for the production of Torch Song Trilogy, that was my big break. That got me out of Maine and to San Francisco.” At 17, Dempsey hopped onto a plane to the other side of the country on the longest flight he had ever been on. “I was ready to take on the world,” he says, laughing. 

And take on the world he has, with an impressive career that has spanned more than three decades. “A lot of things have changed,” he explains. “Awareness, experience. I have a much greater appreciation to be in the business and to have survived over 30 years; I’m grateful for that. I wish I could go back knowing what I know now. I’d probably be a lot more patient,” he says, chuckling. “You want things to happen, but they have to happen in their own time, you know?” With his simple, grounded outlook, Dempsey’s genuine gratitude to the industry is refreshingly humble. 

I question Dempsey on how his career affects his home life and vice versa, and he thoughtfully responds, “I think right now it’s really about finding that balance between work life and family life, and being present for the kids and things like that. I think it’s really important, because that life experience helps inform what you bring into your next performance.” Happily married with three kids, Dempsey is a dedicated family man, and it shows. “I always tell my kids to listen to their heart. The best compliment is that they’re polite and they’re well mannered and they’re kind. I consider that a success,” he says, smiling with unmistakable pride.

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PHOTOGRAPHY BY ERIC MICHAEL ROY
WORDS BY EMMA UNGARO
STYLED BY WARREN ALFIE BAKER
GROOMING BY JILLIAN DEMPSEY
ART DIRECTION BY DOUG MCLAUGHLIN
LOCATION MALIBU, CA