Man at His Best

Patrick Dempsey Is Doing All He Can Before The Sun Sets On Him

How The TAG Heuer brand ambassador juggles between endurance racing, family, and acting.

BY Wayne Cheong | Dec 15, 2017 | Film & TV

Photographs by Mitchell Nguyen McCormack, Styling by Nina and Clare Hallworth, Grooming by Jillian Dempsey

Having arrived in Singapore mere hours before our interview, he reveals that the rest of his day is packed—he’s here as a TAG Heuer ambassador, and will glad-hand the press and the public before flying off at two in the morning to LA for a day, and then to Montreal for a shoot. “I’ve had shorter,” Dempsey says, brushing off how hectic his schedule is.

There’s a tired metaphor of how we are but mere passengers on the road that is life. One can also easily equate life to an ascending elevator or a butterfly’s chrysalis. I’m thinking of ways to begin a write-up of a personality who I’ll be interviewing while stuck in traffic that’s tyre-meltingly sluggish; all credit due to closed-off roads in preparation for the impending F1 weekend. The personality in question is one Patrick Dempsey, 51. He’s an actor, and while I’ve yet to watch an episode of Grey’s Anatomy, I’m aware of his days on the popular Shonda Rhimes drama, and how all-encompassing it was in his life. 

When we meet, Dempsey is a little “out of it”. Having arrived in Singapore mere hours before our interview, he reveals that the rest of his day is packed— he’s here as a TAG Heuer ambassador, and will glad-hand the press and the public before flying off at two in the morning to LA for a day, and then to Montreal for a shoot. “I’ve had shorter,” Dempsey says, brushing off worries of how hectic his schedule is. “I had to do a trip to Spain for dinner once, and then head off after that. You get used to it.” 

Still, he is chipper, all teeth set in the upturned crescent of a mouth. He doesn’t look tired though, older, yes; like all of us, no matter our status, we fall under the judgment of cruel time, but Dempsey does so with flourish— the salt in his hair, the five o’clock scruff, the diffused map contours on his face. He’s staggeringly down-to-earth. He confesses that he flew in alone; no manager, no entourage, just him. He prefers it that way, he adds.

Suit by Salvatore Ferragamo, pullover by Louis Vuitton and Autavia timepiece by TAG Heuer

Dempsey is currently involved in the production of The Truth About the Harry Quebert Affair. Adapted from the book of the same name by Joël Dicker, it’s an intricately plotted tale of a man’s accusation of murder. It made for such a potboiler that it sold over a million copies. Dempsey read the book before even being offered the script, but other than his role as Quebert (“It’s a real departure from what I’ve done in the past”), what really excited him was that fact Jean-Jacques Annaud is helming it. “I’m learning a lot from him. We shoot with three cameras,” Dempsey says. “So, there’s a wide shot, a close-up and another close-up all at once. We capture everything, and then move on to the next scene.” 

Produced by Epic and MDM Television, The Truth About the Harry Quebert Affair will be played out in a 10-episode series. Dempsey sees the adaptation to TV as fitting; instead of condensing the 670-page tome into the conventional 90-minute format, taking time to tell the story and develop characters is a more prudent option. He sees the signs, the shifting trends of television viewing. “I think people like to binge watch. It’s where we’re at right now with technology. Of course, that might change eventually.” 

Suit by Salvatore Ferragamo; shirt by Louis Vuitton; tie by Loro Piana; Monaco timepiece by TAG Heuer.

Back then, Dempsey was locked into his role on Grey’s Anatomy. His character, Dr Derek Shepherd, was a hit with viewers. But while it secured him a long career, playing “McDreamy” eventually boxed him in as a heartthrob. His presence in films became mostly romantic comedic leads (Enchanted, Made of Honour, Bridget Jones’ Baby) and he had limited opportunities to do anything dramatic. “Until people see it, they won’t believe you can do it.” 

Then, the light at the end of a long tunnel: Dempsey caught the racing bug. “I started doing the smaller racing series, and three years after that, I wondered, is it possible to do this?” 

His love for automobiles started at an early age. Dempsey remembers his father bringing home Matchbox cars for him to play with. He’d pore over car magazines; seeing the contours of the headlights dip towards the back of the Jaguar XK120, a young Dempsey couldn’t believe something like that could be possible or even existed. His family lived in an area where he’d watch cars pass by. “I would see some exotic cars, which was rare because I lived in a rural town in Maine,” Dempsey says. “It was only when I got to Los Angeles that I was just blown away by what was on the road. I couldn’t believe that people could afford these cars.” 

His father used to race, and perhaps that rubbed off on Dempsey. He can picture the throttle of the engine, the lingering scent of gasoline, the way adrenaline shoots through his body when he’s behind the wheel, all these things and more get to him. The element of danger is always there, like an afterthought, but Dempsey pushes it out of his mind because once you’re in the driver’s seat, you have to deal with the present; thoughts of mishaps on the road become a non-issue.

Dempsey was realistic about his chances as a pro-racer. Not only was it nigh impossible to be a professional at his age, he was carried along by the momentum of Grey’s Anatomy. “The notion of being a racing actor is conflictory by nature,” Matt Stone, an automotive writer, says. “Studios have to run on a schedule. Racing by nature burns downtime like crazy.” So, Dempsey burned his candles at both ends—balancing acting with his seasonal racing, but sometimes, the scales tipped; while his stardom helped him secure sponsorship (Dempsey professes a “fantastic relationship with TAG Heuer”), shooting ate into his training. “So, it was impossible to be a professional,” Dempsey says, “but I knew I could go far as a pro-am (professional-amateur) driver in endurance racing.” 

Suit by Salvatore Ferragamo; shirt by Louis Vuitton; tie by Loro Piana; Monaco timepiece by TAG Heuer.

Born and raised in Lewiston, Maine, Dempsey wasn’t meant to live out the rest of his life there as well. One of his first few brushes with entertainment was when his shop teacher taught him to juggle. Dempsey picked up the skill and performed for birthday parties on the weekend; he wanted to join the circus but was denied during the application process. 

At 12, he was diagnosed with dyslexia, which is of import especially for actors who need to read scripts. It was a bigger hurdle back then. There wasn’t much information on the condition and he was diagnosed late in life (things occurring late in his life seems to be a prevailing theme) so he developed other ways to read, to understand the words on a page. “I developed skills to fire up that part of the brain, to bridge that disconnect.” 

He left home at 17 for New York to pursue a career in acting. New York, at the time, as he recalls, was “unsafe”. He auditioned, acted, subsisted on “cold water hot dogs” but it was an experience that he took on before clinching his first film role, In the Mood, at 21. This career momentum would eventually lead him to Grey’s Anatomy. 

“I was locked into that show for 10 years,” Dempsey says, “so that eliminated a lot of opportunities because there was so little time for me [to pursue any film-related things]. With my racing schedule in the off-season, I had no desire to do any film work.” 

So, he continued with the show until he came to a point where there was little else left to be discovered with his character. He was spending too much time away from his family and the opportunity to race a full season in the WEC (World Endurance Championship) with Porsche came up. Dempsey didn’t want to miss that opportunity. 

Addressing concerns about his leaving the show, he says, “People didn’t want me to change, they didn’t want me to move on, certainly the fans didn’t, and that’s understandable. I get that. But there’s always the 250 episodes that I was in that they can revisit.” Stepping away from something that’s safe and comfortable is always difficult, but Dempsey has a more nuanced view: “It goes back to the idea of change: you’re not growing if you’re not changing. No change means stagnancy, it means there’s atrophy.” 

And in a literal move to avoid stagnancy, Dempsey committed himself to endurance racing. 

Suit and turtleneck pullover, both by Prada; Monaco timepiece by TAG Heuer.

It is the world’s oldest endurance car race. The 24 Hours of Le Mans is held annually in June at the Circuit de la Sarthe, a semi-permanent racecourse that has gone through several configurations in its 94 years of operation. The 13km strip of asphalt puts the drivers and their cars through the works. While speed is king here, technique is its de facto twin; even before they get into the car, they have already played outmanoeuvring the roads in their minds a thousand times. For Dempsey, the mental plain is key. “I think meditation is very important. [While] I don’t do TM [Transcendental Meditation]. I sit in the morning and breathe. I calm myself, have my thoughts come and go. I encourage that with my kids.” 

His relationship with racing has also helped with his acting. The level of preparation and the focus needed on the track translate to what is expected of him in front of the camera lens. 

The comparison with Steve McQueen often comes up. Both are working actors who are also racers. “You grow up with the images of McQueen and Le Mans,” Dempsey gushes. “[McQueen] never raced there but I raced there four times and eventually got onto the podium.” 

In 2015, Dempsey Racing came in second. There are videos of an elated Dempsey pumping his fists, eyes crinkling from beaming. When he is asked for his thoughts on the race, his voice cracks as he’s effusive with thanks and love. It looks like this is the most important moment of his life and nothing will stop him from taking it further. 

And then a few months later, Dempsey announces that he’s stepping back from racing. 

This comes after he wins the 2015 FIA World Endurance Championship in Fuji, Japan; after 68 races; after a promising career season. Dempsey puts it all aside and releases a statement to say that he’ll be focusing on “family and acting” from now on. He remains as team owner of DempseyProton Racing. 

“It was a very hard decision,” Dempsey says. “I love racing. I love the world. I love the competition. I love the spiritual and emotional experience it gives you.” There’s a slight halt as though he’s come to terms with the reality of his situation. “But I knew that if I were to get to that next level in racing, it’d need to be a full-time commitment. Even at an am-category, those drivers are focused 100 percent.” 

Suit by Salvatore Ferragamo; shirt by Louis Vuitton; tie by Loro Piana; Monaco timepiece by TAG Heuer.

If Dempsey were a younger man with fewer responsibilities, and no children, he’d go all out. But he is not any of that. He is a man who is sure-footed in the now. “I didn’t want to miss out on [racing]. I had to step back to re-evaluate. Also, had I not achieved my goals, it would have been a lot harder, but once I’d achieved them, I was okay,” he says. 

“Unfortunately, when you’re on a show, you’re racing for time because there’s no time. You gotta crank it out. So, I took a year off from everything to stay home with my family to reassess what it is that I want to do moving forward. So, I think Harry [Quebert Affair] is the right direction, and working with Jean-Jacques is definitely the direction that I want to go. The experience I’ve had with Porsche and the quality of preparation is really what I need to apply to my career as an actor. I’m starting to feel that type of focus and energy with the project I’m currently on.” 

Suit, pullover and shirt, all by Louis Vuitton; shoes by Martin Margiela.

Dempsey is doing so much now. Because of the diverse worlds that he occupies—racing, philanthropic work, acting—, there are aspects that he’s working on that he finds satisfying yet doesn’t take on more than he can handle. 

He thinks LA is a bubble, and so advocates the importance of travel. That’s the only way to get a better perspective of how the rest of the world lives, he adds. This worldview is already tempered by his racing episode that saw him travel extensively. “You can’t take yourself too seriously. I just have a job that’s highly visible, but I’m not any better or worse than anyone else.” 

Apart from California, he calls a small lakehouse in Jacksonville, Texas, home; the latter seems more suited to him. His Instagram is peppered with his excursions in Texas, sometimes to a local pie shop, another time out on a boat, fishing. There are no #ootd shots on his feed; just slices of his life, things that he’s into. “I don’t put any captions,” he points out. “That’s just to mess with people, get them to engage.” 

While he’s working on The Truth About the Harry Quebert Affair, Dempsey is producing a documentary on American race-car driver, Hurley Haywood. He has his fingers crossed that he’ll get it done by the end of 2017. 

There is another reason for his love of racing: it’s the relativity of time. “In racing, when you’re fast, that’s when everything slows down. I think it’s important to embrace change,” Dempsey says, his features softening as he articulates a realisation that appears to have dawned on him years ago. “And change is time. Things are always moving forward. It’s important to be present, which leads to mindfulness and being in the moment. That’s what racing really taught me. That’s my relationship to time, and that’s to be present. 

“I’m enjoying life right now, taking my time and moving on to the next thing. 

And this is rare for me.” And then it is time to go. Dempsey smiles warmly. He is keen to check off the rest of his list before hopping on to the next plane out to chase the sun again.

This feature was first published in the print edition of Esquire Singapore, December 2017.