Patrick Dempsey Breaks The Spell

Patrick Dempsey seems frazzled. That is, Robert Philip, his character in Disenchanted, Disney’s follow-up to the 2007 fish-out-of-water fairy tale Enchanted, looks harried. He’s dressed impeccably for a day at the office — navy suit, crisp white shirt, and dark tie. But he’s running late for the commuter train and keeps checking his watch (is that a TAG Heuer?) as he’s being chased. His pursuer: Prince Edwards from Andalasia, the fairy-tale land his wife hails from, who is trying to bestow upon him a sword to “slay the demons.” Robert, a lawyer living in the suburbs of, let’s say, New Jersey, is just trying to get to Manhattan to meet a client.

Dempsey might as well be playing himself here, a handsome, kind, and charismatic man who has had grand expectations thrust upon him. This is after all McDreamy (11 seasons of Grey’s Anatomy); Prince Charming (Enchanted, now Disenchanted); Mr. Right (Can’t Buy Me Love, Made of Honor); a dad of three and husband for 23 years; a man who runs a cycling charity and seriously races sports cars; a guy who can play perfect pretty well on screen or in life.

But wait. Patrick Dempsey would like to go on the record that perfection is bullsh*t, struggle is part of life, and growth only comes when we all look behind the curtain. Like he is about to tell me: “No one is perfect, right? We’re human beings. People are going to make giant mistakes.” What Hollywood fairy tales don’t convey is that you have to learn these lessons over and over again. “I think whatever the karmic value of an action is, it’s going to take its time for it to be resolved if we can work through it. I think … the thing that we don’t teach our kids is you make a choice, you’re going to deal with those choices. We are here to fail. We are here to learn.”

“No one is perfect, right? We’re human beings. ... We are here to fail. We are here to learn.”

Dempsey is Zooming from his home in Maine, not far from the small town of Turner, where he grew up. His father, an insurance salesman by trade, was much older than his mom, a school administrator. “He had me later in life, in his 50s,” Dempsey says. “He was very much there. He was semi-retired, so he was always around. We did a lot together.” They connected through sports; Maine being Maine, skiing became Patrick’s obsession. School, however, didn’t appeal to Dempsey. He struggled terribly with reading. As Dempsey once told Barbara Walters, his struggles landed him in “special ed,” a social curse for kids in those days, one that lacked professional support. He has said he felt “stupid” and acted out to divert attention from academic struggles.

“I was diagnosed with dyslexia much later,” he says, “so anything to do with school was very painful, very hard to deal with. But you can get your identity and self-esteem through sport, and that’s how I thrived.”

Skiing ultimately led him to his calling. “I got into performing accidentally because I was watching Ingemar Stenmark on ABC Sports’ Up Close and Personal,” he says. On this Olympic special, Stenmark, one of the greatest slalom skiers of all time, was showing off his skills on a unicycle. “I ended up picking up the unicycle from the Sears and Roebuck catalog. I started learning how to ride the unicycle, and then this troupe of vaudevillians asked me to perform with them one night.”

He started juggling, discovered a natural attraction to the stage, dropped out of school, and chased a career in acting. “At 15, 16, I left home. I was in New York in 1983 on my own. I was functionally illiterate with no formal education. That’s around my kids’ age now, and I can’t even imagine that as a parent.”

Dempsey found success quickly, making the jump from theater to the screen. His dyslexia made auditioning particularly challenging, so he learned to memorize lines. He broke through in 1987 as Ronald Miller, a dweeb with some cash and a plan in the Brat Pack-style rom com Can’t Buy Me Love. After that Dempsey booked solid work in headlining roles — playing charming young casanovas and self-serious college kids. He spent the mid-’90s and early 2000s as a working actor, taking roles in TV movies and miniseries. Dempsey came into his own in the late ’90s with a series of recurring roles on shows like The Practice, Once and Again, and Will & Grace as closeted sportscaster who falls in love with Will. In 2002, Dempsey had a solid turn in Sweet Home Alabama as Reese Witherspoon’s city slicker fiancé.

In 2005, Dempsey landed the iconic role of Dr. Derek Shepherd aka McDreamy on ABC’s Grey’s Anatomy. The world fell in love with the vulnerable, charming neurosurgeon — and the man who played him. “You realize going into a situation like that, that that’s going to be with you for the rest of your career and … will allow you to transcend to bring in a new audience. It’s opened so many doors around the world. It gave me the opportunity to do things I wouldn’t have been able to do. You have to take the good with the bad.”

It just so happens that when you work in Hollywood, “the bad” hangs out at the end of your driveway with a camera strapped to its neck. “Well, you live in a gilded cage. You know you’re being photographed as soon as you step outside.” Over the years, 11 seasons, to be exact, from 2005 to 2015, Dempsey says the publicity and the show itself started to weigh on him. In his telling, “It’s 10 months, 15 hours a day. You never know your schedule, so your kid asks you, ‘What are you doing on Monday?’ And you go, ‘I don’t know,’ because I don’t know my schedule. Doing that for 11 years is challenging.” During our conversation, Dempsey reflected further on how the show wore on him. “If you’re a celebrity that has any kind of visibility, people are going to clock you and your behavior. How you deal with people is really critical. Then you have something like McDreamy, it’s like this is supposedly the perfect male. How do you hold that? I’m not that at all. I think that was a frustration towards the end of it. It’s like this is unsustainable.”

Dempsey left Grey’s in Season 11, killed off by a car accident. He returned in Season 17, reprising the McDreamy role in the COVID dreams of his former lover, Dr. Meredith Grey. But Dempsey says that his time on Grey’s Anatomy is over. “For me, there’s nothing left there to go back and do at this point. I think the show is trying to find its legs without many of the original characters remaining.”

“For me, there’s nothing left there to go back and do at this point.”

In 1997, Dempsey’s mother, Amanda, was diagnosed with ovarian cancer. Over the next 17 years, Amanda Dempsey went into remission 10 times. In 2008, he created the Dempsey Center, a cancer facility that offers families a menu of therapies and services including access to Reiki practitioners, head coverings and wigs, support dogs, and nutrition classes.

“Patrick’s the kind of person who sees past himself and realizes that there are others who might be impacted more than him,” says Cara Valentino, the CEO and president of the Dempsey Center. “His mother was a big presence in this community. She had a lot of people who wanted to help. But what if you’re alone? You can see it with the way he engages with people in the community. He listens deeply and intently. He is really present.”

In 2014, after suffering her 11th bout with the disease, Amanda Dempsey passed away at the age of 79. Dempsey has said that her illness and passing affected his family profoundly.

In January 2015, Dempsey’s marriage made headlines after his wife, Jillian Fink, a makeup artist and entrepreneur, filed for divorce after 15 years of marriage, citing irreconcilable differences. The couple got back together the next year, Dempsey told reporters, because they weren’t ready to give up on their marriage. Dempsey credits therapy as the key to their reconciliation: “Individual therapy and then I think couples therapy is important,” he says. “Why not utilize those tools? Have someone give you some perspective. What I have learned is that I will hear things differently in a therapist’s office just because we have a little bit of an emotional detachment. There’s room and space to come in and go, ‘Oh, OK. Now I understand where you’re coming from. OK, that’s what you’re feeling. I don’t want you to feel like that’ and then you try to work on it.”

After all marriage isn’t a fairy tale come to life — it’s work. “You’re going to have different wants and different desires as you get older, right? You’re changing, you’re evolving. Then you have to give each other space to be able to go off and do that, with the commitment to come back and continue to strive, and to become a better person as a man or as a woman, as a father, as a mother, as a son, as a daughter, all these things. We’re here to become a better person.”

As a dad, Dempsey recently had to face his own childhood struggles when specialists diagnosed one of his boys as dyslexic. “It was really hard not to shut down and become overwhelmed emotionally, because it just brought back everything that was so difficult from my childhood.” For Dempsey and his son, it meant getting him the guidance that Dempsey never did — that support group that didn’t exist in his childhood. The specialists, the paperwork, the game plan. His son, a twin, is 15, and as Dempsey knows well, has a lot of hard work ahead of him.

“When you have a child, you don’t think about how difficult it is to give them an education and get them through without heavily medicating them. And then you have to be on top of it.” With all of the tools and resources at Dempsey’s disposal, he credits the support and guidance provided by his mother-in-law, a retired educator. “It takes a whole team coming together to get us through this journey.”

Disenchanted opens with Robert, lost in the chaos of his life with a teenager and newborn. As Dempsey calls it, the character is “trying to be all things to all people — he’s got this teenage daughter, and he’s dealing with his wife, [Giselle], who is postpartum and depressed. He’s trying to do what’s right for the family. He’s trying to find meaning.”

This being a Disney movie, the search for meaning is made material when Giselle (Amy Adams) waves a wand while wishing for a more fairy-tale life. Shortly thereafter, Robert becomes a prince, aimlessly roaming the countryside looking for a quest to give him purpose. Disenchanted director Adam Shankman sees a lot of Dempsey in this character. “Robert and Patrick are in many ways aligned as human beings,” says Shankman. “Patrick cares very deeply about his family — it’s so undeniably true. He is also always searching. He’s a curious person. He’s adventurous. What I don’t see in Patrick that’s in Robert is a sense of dissatisfaction. Robert wonders, ‘What is the truth about this chapter in my life, and where does it go from here?’ Patrick has that life experience already.”

When talking about Robert, Dempsey offers what sounds like some very good life advice for the character: “Anything you can do to take yourself away and clear your mind and get some distance, the better off it’s going to be.” In real life, for Dempsey, this peace of mind is found behind the wheel of a car.

Dempsey is serious about racing. He debuted in 2007 in the North American Rolex GT Series; competed in 24 Hours Of Le Mans, the renowned endurance race in France two years later (to an impressive ninth place in the GT2 class); finished sixth in Rolex 24 at Dayton while filming for Transformers: Dark of the Moon in 2010; took to the track in the American Formula 1 debut in 2012; and took third place in the Circuit of Americas race in 2013. At that time, he made clear that motorsports were his priority. “If I could just walk away from acting,” he told a reporter in 2013, “I think I could do that very easily, and just focus on the driving. I would love that more than anything else.”

“You just feel alive, you feel present. You’re forced to be in the moment; you can’t be distracted.”

You can see the truth in the statement in the 2013 documentary Racing Le Mans. In it, Dempsey trains hard for the race both physically (with race-specific workouts that would put Chris Hemsworth to shame) and mentally, with hours on the track and hours in the back looking at the data, poring over weaknesses in his turning and braking. You see a lot of Dempsey’s furrowed brow. He’s hard on himself, learning and improving impressively according to his fellow drivers, but never satisfied with his effort.

This, from a laid-back leading man, a newly retired McDreamy whose fame and fortune have already been cemented. So why does racing call him? “I think it’s the mindfulness of it,” Dempsey says. “You just feel alive, you feel present. You’re forced to be in the moment; you can’t be distracted because you have to have total concentration. I think that’s it.”

These days, Dempsey is still taking acting gigs, but he’s picking and choosing the ones that work for him. Disenchanted, for example, was clearly a pretty sweet gig. The days were short, with a hard stop at 10 hours and strict European COVID protocols; the cast members are accomplished adults (all the leads are in their late 40s or 50s); and the Irish countryside offers a nice background. “Disenchanted was a very happily aligned set,” says Shankman. “Everybody got along. There was an enormous amount of familial camaraderie. Patrick and Amy have an incredible repartee — giving each other sh*t in a completely loving and respectful way.” Dempsey particularly enjoyed exploring Ireland. “I had never spent any time there,” he says. “The role I have is really a supporting role, so I had a lot of time off to explore. I brought my family with me, and we had an opportunity to immerse ourselves.”

Because when you’re 56, with a daughter in college and two teens eyeing the exit, a car racing team nabbing wins and an acting career that just won’t quit — you need to seize those perfect moments when they happen. There will be plenty of time to work through the rest.

Top Image Credits: Officine Générale coat, sweater, and pants, Buck Mason T-shirt, talent’s own ring, Bombas socks, Reebok sneakers.

Photographer: Eric Ray Davidson

Stylist: Warren Alfie Baker

Set Designer: Kelly Fondry

Grooming: Jillian Dempsey

Talent Bookings: Special Projects

Video: Sam Miron

Associate Creative Director, Video: Samuel Schultz

Photo Director: Alex Pollack

SVP Fashion: Tiffany Reid

SVP Creative: Karen Hibbert