Hollywood hits the Hamptons this weekend with the star-studded buzz surrounding the Hamptons International Film Festival. Undeniably, one of the most charming leading men on the big screen is Patrick Dempsey, who graces the new Manhattan magazine October issue, where he discusses his first audition for Grey’s Anatomy, his philanthropic efforts in honor of his late mother, Amanda, and his burgeoning car racing career. Donning a wardrobe by Sacoor on the cover and in the inside shots, Dempsey sports the ultimate look of men’s Hamptons style. MANHATTAN magazine shares their new cover feature, written by Ayesha Khan, with KDHamptons readers below:

Lewiston prides itself on being the second largest town in Maine, but it’s typical of New England—red-bricked and lined with church steeples. But as ordinary as the town may seem, famed native son Patrick Dempsey— who overcame dyslexia, excelled in juggling, then skiing (he boasts a state slalom championship) and finally in theater, all before leaving home to conquer Hollywood— is truly extraordinary.

As Grey’s Anatomy emerges from its summer hiatus, its leading man makes his way to the set, casually clad and with an ever-essential baseball hat. “It’s amazing people are still into [Grey’s Anatomy] after 11 seasons; it’s remarkable!” Dempsey says with an effervescent smile. After more than a decade of success and critical acclaim, Dempsey takes some time to reminisce about his first audition; in fact, it still elicits quite a hearty laugh from the actor. “I remember going into a room full of people, but I just remember how calm and stoic [Grey’s Anatomy creator Shonda Rhimes] was. At first I thought she hated me, but she was calculating in her head where to put me and what I’d be right for. We always laugh about that first encounter. They liked me, but they wanted me to do a chemistry read with [lead actress Ellen Pompeo]. I had an immediate connection with her because she has a Boston accent, and I’m from Maine, so that disarmed me.”

But as Dempsey—who had appeared in his share of unsuccessful pilots—recalls, being cast for the show was no guarantee that it would mean a steady gig. “The actor’s odyssey is: OK, I need to get the job; I got the job, but, oh, no, will the show get picked up? And when the show is picked up, will it stay on the air, and once it gets on the air, will it do well in the ratings?” Grey’s Anatomy’s performance in the ratings is the stuff of television legend, with the show garnering a host of accolades from Emmys to Golden Globes to Screen Actors Guild awards. It has been quite a journey for Dr. Derek “McDreamy” Shepherd, lined with a vindictive ex-wife, a doe-eyed intern girlfriend, competitive co- workers, several brushes with death (one at the hands of a mass shooter and one in a plane crash), a second marriage, kids and personal calls from the president. “Sometimes it’s hard for me to see the perspective—I can’t see the forest for the trees,” Dempsey says of his character’s progression over the seasons. “I think his priorities have become much more his family than his career objectives. I think he is really at a crossroads to determine what it is that he’s wanting to do.” When asked about the upcoming season, he is understandably tight-lipped, but does offer a few hints. “What happens with the opportunity of Derek going to D.C. or not and how that affects [his and Meredith’s] relationship, as well as Meredith’s past and her relationship with her family, lends itself to the dynamics of what’s happening this season.”

Dempsey can certainly relate to the character’s ever challenging work-life balance, with his wife, Jillian; three kids; and a shooting schedule that occupies him relentlessly from July to May. “My schedule is completely out of my control because that’s the nature of being on a network television show,” he explains of not knowing what to expect from week to week. When he’s not busy shooting, Dempsey feverishly reads books and sifts through scripts to find the next project for his production company, Shifting Gears Entertainment. The company has an overall development deal with ABC Studios and has also optioned a book called The Limit for a SundanceTV project. This venture is a drama series based on the real-life story of California mechanic Phil Hill, who went on to become the first American-born driver to win the 24 Hours of Le Mans and the only American-born driver to win the Formula One World Drivers’ Championship. “It’s sort of like Mad Men in the racing world of the 1960s,” describes Dempsey, his voice lighting up with the fervor of a child telling a fantastical tale.

The fervor is fitting, given that Dempsey is an avid racer himself, having competed at prestigious events such as the Rolex Sports Car Series and 24 Hours of Le Mans, where he has placed fourth and fifth but is still keen to capture the title. Still, for someone who once sped down slopes and has always loved racing and cars, it took a Skip Barber Racing School gift certificate from Jillian to procure his Sports Car Club of America license, the first step to becoming a qualified track racer, that stirred in Dempsey a deeper enthusiasm for the sport.

Ironically, “I think she kind of wishes she hadn’t allowed me to start racing because it’s become a full-time business and occupation outside of, and on top of, everything else I’m doing,” Dempsey admits, adding that Jillian, too, has recently been bitten by the racing bug. “She got the new Porsche 911 Targa as an anniversary present and now says, ‘I completely understand why you love cars and the rush of it!’ If you’re in a performance car there’s definitely a sensation that you get that is indescribable.” As for picking his own favorite sports car—from his own expansive vintage car collection, no less—Dempsey quickly reveals the Porsche 356 as his top choice, one his paycheck from the 1987 breakout film Can’t Buy Me Love made possible. “I will never let go of that car; it will always be symbolic to me. It’s reliable, it’s fun and it evokes a very strong emotional response from people.”

Having traveled the world to race, Dempsey strongly advocates stepping outside one’s own comfort zone to experience new cultures. “It allows us all to have more tolerance for people. I think right now that’s more important than ever,” says the jet-setter, who has been everywhere from Asia and Europe to Latin America, singling out both Brazil and India as particularly “eye- opening” experiences. And though he has an affinity for “boutique-y” hotels, such as New York’s The Greenwich Hotel and Georgia’s Barnsley Resort, Dempsey admits that the best way to immerse oneself in a destination is to rent a local home. As for travel tips from the seasoned frequent flier, he offers, “I try to pack everything that I need in one bag so that I don’t have to check it. That’s the key. I just hate standing in line waiting for my bag to come out!”

Soon after our chat, Dempsey travels back east, where his aforementioned hometown is coming together in all its festive finery to walk, run and cycle in the Dempsey Challenge, an event that supports the town’s favorite celebrity and his passion project—The Patrick Dempsey Center for Cancer Hope & Healing, which offers free therapeutic yoga and reiki sessions, support groups, events and activities for those stricken by cancer and their families. This year the Dempsey Challenge hits particularly close to home as the actor’s own mother, Amanda, passed away from ovarian cancer after a 17-year battle. “My experience with my own family, my mother with her diagnosis and her journey, and her finally succumbing to cancer this year, is that the doctors have such a huge workload; they’re trying to do everything that they can; the nurses are so vitally important as well—but then what happens to the caregivers and the family members?” Dempsey asks. “There is a real void, and that’s how the center came about, [with the] thinking: How do we help those people? The human touch is so healing, and when people come into the center, they’re greeted usually by cancer survivors themselves who already know what’s going on and are compassionate. I think that’s really important, and sometimes you don’t get that.” Ultimately Dempsey hopes to ally his center with others around the country. “What we’re trying to do now is really network with other like-minded wellness centers so that we can start to have a strong dialogue,” he explains.

Whether breaking hearts while saving lives on TV, roaring around a racetrack in France or offering a compassionate hand to those affected by illness, Dempsey takes on each of his roles with true dedication. And, with true sincerity. He ends our conversation with, “Thanks so much for taking the time to talk to me,” proving that, even in Hollywood, humility has its charms.

** Photos in this feature by John Russo

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