The Untold Truth Of Patrick Dempsey

Patrick Dempsey's career has been fascinating, considering how long he worked in the industry before truly breaking out with his role as Dr. Derek "McDreamy" Shepherd in the juggernaut hit series "Grey's Anatomy." Perhaps even more interesting is how he got to Hollywood from a small rural town in the first place — a very unique journey that actually included juggling and a unicycle. Once he began acting, Dempsey was by no means hurting for work. He was a teen movie staple in the late 1980s, notably appearing in "Can't Buy Me Love" and "Some Girls," as well as "Fast Love," the short-lived TV adaptation of "Fast Times at Ridgemont High." Dempsey worked consistently in television and film in the 1990s, but it was "Grey's" that made him a household name in 2005.

After leaving "Grey's Anatomy," Dempsey has appeared in a number of projects, including the TV series "Devils," the much-anticipated "Enchanted" sequel ("Disenchanted"), and the film "Ferrari." The latter must have been a real treat for the actor, a race car driver whose love of cars is perhaps only paralleled by his love of watches (he's a Tag Heuer ambassador, after all) and home renovation. Add producer — and dad — to his list of jobs and the man clearly has his hands full. And as if all of that were not enough to warrant our attention, Dempsey's personal life has had a lot of unexpected turns as well. Heck, even his charity work has a riveting story behind it. Here is the untold truth of Patrick Dempsey.

School may not have been Patrick Dempsey's thing, but he certainly excelled in other areas, like juggling, for example. The star finished second in the International Jugglers Association Championship, and it is juggling that led to his career in show business. "I didn't know I wanted to be an actor," he said in an interview with Nobleman Magazine. "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." In addition to juggling, Dempsey also rode a unicycle, did magic, and even puppetry as a member of a Vaudeville act (which he has also referred to as a circus). Soon after joining the act, Dempsey dropped out and left for New York City.

Dempsey also won a New York City talent competition around this time, which helped him get an agent. Harvey Fierstein also played an integral role, discovering Dempsey in his act and inviting him to audition for a play he was casting. After his casting in the 1984 production of Fierstein's "Torch Song Trilogy," it was not long before Dempsey landed on screen. His first screen credit was in the 1985 film "Heaven Help Us," and things spiraled upward from there. As for his degree, Dempsey got that in 2013 when his high school awarded him an honorary degree — at the same time that Bowdoin College gave him an honorary doctorate.

Patrick Dempsey has utilized his love of cycling to do good in the world by way of his annual fundraiser, called the Dempsey Challenge. The event — which includes both cycling and running components — has been happening since 2009 and has raised over $18 million since its inception. But the fundraiser is just a part of Dempsey's larger commitment to cancer advocacy and care for those with cancer. All proceeds go to the Dempsey Center, an organization Dempsey founded to help people diagnosed with cancer and their caregivers. The Center is based in Lewiston, near where Dempsey was raised, and was founded in honor of Dempsey's mother, Amanda. Amanda was first diagnosed with ovarian cancer in 1997 — which prompted Dempsey to become a vocal advocate — and on her 11th recurrence, passed away in 2014.

Dempsey utilized his rising celebrity to found the Center in 2008, with the goal of providing personalized services for those in his local community to couple with their medical care. Amongst other things, the organization offers access to wigs and support dogs, cancer education classes and counseling, fitness workshops, support groups, Reiki, massage, and acupuncture — all for free. "We don't treat the disease; we treat the person," Dempsey explained in an interview for the watch brand Monochrome's website. "We spend a lot of money on research and development for drugs, and we need to continue to do that. But what we are really missing is the human side and caring side of cancer treatment, and that is what we provide."

There are many perks to being the leading man on a fantastically popular network TV show, but the schedule is not one of them. It means being on the job most months of the year, and when you are on set, you're there for two-thirds of your days. Dempsey was on "Grey's Anatomy" — which had a short first season, but often exceeds the standard 22 episodes a season and pumps out 24 or 25 — from 2005 to 2015, but the schedule eventually became too much for him to bear. "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," he told Fatherly. "Doing that for 11 years is challenging."

Part of Dempsey's issues with lacking power over his own time, aside from the family stuff, had to do with his passion for racing. "[The showrunners] were pissed because I was racing," he told British GQ. "With a show like that, you're at the mercy of what the show wants to do. I wanted to be more in control of things, and there's nothing like control behind the wheel." After leaving "Grey's Anatomy," Dempsey started saying yes only to acting opportunities that could accommodate his other passions and family life. He seemed like he was ready to put network TV behind him for good, but he almost returned in 2020 (the pilot for "Ways & Means" was not picked up).

As we noted previously, Patrick Dempsey first got married at age 21. That marriage ended in four years, although the divorce took another three to become official. He met his current wife, Jillian Dempsey, the same year as his divorce when he was a client at her salon. The pair married in 1999, and they are still together today. That does not mean there have not been hurdles, however, and things got so bad at one point that divorce was on the table. We mean that in the official sense, as Jillian — a celebrity makeup artist with a successful beauty line — filed for divorce in 2015. The divorce never happened, but the couple remained separated until the following year.

The Dempseys actively worked on their marriage during their time apart, no doubt motivated by the way that a reconciliation might benefit them and their three children. Patrick has credited the counseling they did with helping facilitate their reunion. "Individual therapy and then I think couples therapy is important," he told Fatherly. "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." With their oldest child Talula now an adult and their twins Sullivan and Darby approaching college age, the couple will be empty nesters before long — but they clearly know how to handle whatever issues change brings forth.

True Patrick Dempsey fans know that he's a passionate car lover who has had an entire second career in racing. Unlike acting, which Dempsey started doing as a teenager, racing cars was a passion that came about later in life, although the interest was always there. "I've always been a fan of racing, ever since I was a kid," he told Jetset Magazine. "My dad was a big fan, and we used to watch the Indy 500, Daytona, F1, all of that stuff. That was great, because [Speed Channel] used to show all of the old races, all of the live races." Though he followed the sport, Dempsey only started to explore driving himself after his wife sent him to Skip Barber Racing School for a three-day course.

Dempsey was 38 when his wife got him that gift, and he credits that course, along with meeting a race car constructor at an Atlanta charity event, with starting him on his path to becoming a semi-pro racer himself. He quickly made up for lost time, competing in the prestigious 24 Hours of Le Mans race four times, where he took second place in 2015. Dempsey has competed in plenty of other races — including the Rolex 24 at Daytona and the Mazda Raceway Laguna Seca — but stopped racing competitively after hitting the Le Mans podium. "I miss being competitive, and I miss racing," he told Haute Living in 2016. "But I really wanted to focus on developing the next step of my career."

Since Patrick Dempsey's racing team has a Porsche partnership, his relationship with the brand has been a long one. His work with Porsche Designer Eyewear is a natural extension of this pre-existing relationship with Porsche, a brand Dempsey has long admired. "It's the aspiration of what they are putting out there. I've always loved it since I was a little kid," he told The Hollywood Reporter. Porsche Design began with watches in 1972, and it branched out to sunglasses in 1978 when it developed the first-ever pair with interchangeable lenses. With that face and that hair, coupled with his connection to the car world, Dempsey was a natural choice for an ambassadorship — a job that is mainly about looking good in the product in both photos and in person.

Dempsey started with Porsche Design Eyewear as an ambassador in 2021, and it must have been a huge kick for the actor, who used the money from one of his first films to purchase his first Porsche (a 356 cabriolet) more than three decades earlier. Porsche Design Eyewear by Patrick Dempsey, released in 2023, was the star's first time on the creator side. Dempsey was very involved in the design of the limited edition collection, which consists of two sunglasses and two prescription frames, with different color combinations available. "It's exciting because you're learning something new. You're learning about a different craft, the technology and the history of Porsche — the design, their attitude and culture," he told People of the experience.

Certain celebrities have physical features so magnificent that they have become an integral part of their brand, as well as the cultural landscape. Think Brooke Shields' eyebrows, Tina Turner's legs, or Cindy Crawford's mole, for example. It is slightly less common with male celebrities, but it would be hard to disagree that Tom Cruise's middle tooth or Zachary Quinto's eyebrows weren't iconic as well. Patrick Dempsey is 100% on this list, because part of what made McDreamy so dreamy was Dempsey's thick, wavy hair. Its amazingness only became amplified when Dempsey started graying, and those salt-and-pepper strands became his physical trademark.

For a lot of people, it is hard to imagine Dempsey with different hair — but there is no need to envision it, because Dempsey got rid of his luscious silver mane in 2022 when he bleached his hair blond for his role in the film "Ferrari." The whole process took six hours, and Dempsey stated he freaked out during it. The end result was polarizing, and Dempsey has been clear about knowing the importance of his natural color in his screen persona. "It's fun to do something different. Unfortunately, or fortunately, I'm known for my hair. So, this has really jacked up a lot of people, they don't know how to embrace it. Either they love it or they hate it," he told Variety. When he was unable to get his salt-and-pepper back by dying his hair, Dempsey went ahead and shaved his head — which was even more jarring than the blond.