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.

Until age 12, Patrick Dempsey lived in Turner, Maine, a tiny town in the Lewiston-Auburn metro area, and after that, in the even smaller Buckfield. Dempsey has said he bicycled miles when he needed to get to the nearest resources, but even the area's biggest town, Lewiston, lacks train access — the existing station was built in 1874 and is a historical landmark, but has not been in use for a long time — so he rarely traveled far. School was always difficult for Dempsey, who was placed in special education courses because of an undiagnosed learning disorder. The star attended Leavitt Area High School, but struggled to the point where he dropped out before getting his degree. "I was diagnosed with dyslexia much later," he told Fatherly. "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."

As a youngster, Dempsey spent a lot of his time either skiing or exploring the woods, and that way of life is clearly still appealing to the actor, who maintains a home very close to where he was raised. "Now that I have a place in southern Maine, I get to go back and connect to the land. I have a place to center and reflect on where I've come from and where I'm going. It brings up a lot of emotion and memories," he explained to Maine Magazine. Unsurprisingly, Dempsey has said he hopes to retire somewhere in Maine or the English countryside.

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 is a big sports guy, and we will talk about some of his endeavors — like cycling and racing — later. But there is one particular sport he developed a love for early on, and it is very much a New England staple: skiing. Skiing was perhaps Dempsey's biggest childhood interest and he had hopes of one day making the Olympics as part of the United States Ski Team. At 15, he won the Maine High School State Slalom Championship and may have continued down that route had it not been for a bad accident. Though he physically recovered from the spine compression he suffered during a pre-race run at Sugarloaf Mountain, Dempsey's skiing had changed. "I lost something. I never skied with the same speed," he told Men's Journal.

Dempsey still skis regularly and is even on the U.S. Ski & Snowboard Foundation's Board of Trustees (as of 2020). His family has a home in Utah's Deer Valley, and they love to travel to places like Switzerland or Austria, where the mountains are remarkable. In 2018, he told The Telegraph that Lech, Austria — a teeny tiny mountain town in the state of Vorarlberg — was his best-ever holiday due to the food, architecture, and slopes. Even though skiing was supposed to be Dempsey's path to the Olympics, it is one of his other passions, cycling, that got him there. The actor was invited to be an honorary captain for the USA Olympic Cycling Team at the 2020 Olympics in Tokyo, Japan.

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."

Before he was McDreamy and had those glorious salt-and-pepper locks, Patrick Dempsey was still hunky in a more low-key way. We are sure he had no problem attracting ladies his own age, but young Dempsey instead fell into a relationship with a much older woman — and then he married her. The actor was only 18 upon meeting Rochelle "Rocky" Parker in 1984 when she played his aunt in the play Brighton Beach Memoirs. Parker was 44 and had three kids, including actor Corey Parker, who is Dempsey's best friend (they supposedly became friends after he married Rochelle). Dempsey was barely legal drinking age when the pair married in 1987, which was young even for the time. For comparison, their age gap of 26 years was larger than his age of 21!

Despite the age gap, Dempsey and Parker had a handful of happy years together before their 1991 split. Parker allegedly filed for divorce because Dempsey met someone else, and things got pretty nasty after that. In court papers, Parker alleged physical abuse and said that Dempsey broke her finger by slamming it in a car door during the making of "Can't Buy Me Love." When these allegations became public following Dempsey's "Grey's Anatomy" success, Parker sang a different tune — kind of. She first told the National Enquirer the violence was a one-time thing, but days later, released a statement confirming the allegations were false and that she only made them due to some poor advice. Parker died of cancer in 2014.

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).

"Grey's Anatomy" has been known to have a lot of behind-the-scenes drama, and Patrick Dempsey has been the source of some of that. He left the show amidst reports of tension on set, and subsequent interviews with cast and crew have painted Dempsey more than a bit difficult toward the end (this is an at-length topic in the 2021 book, "How to Save a Life: The Inside Story of Grey's Anatomy," an oral history that diehard fans should definitely seek out). In response to the diva title he received, Dempsey has been refreshingly honest. "I can understand why people would say that," he told ABC News in 2016. The bad blood was only temporary, it seems, as Dempsey has since returned for a guest arc.

The behind-the-scenes drama is perhaps why Dempsey did not cry upon filming his final scene in 2015. In his exit interview with Entertainment Weekly — with journalist Lynette Rice, who wrote the oral history book— Dempsey said his last day was just like any other. He may not have felt emotional then, but the actor certainly got the feels when he returned in Season 17 for four episodes, playing McDreamy in an ailing Meredith's dreams. "We all cried at the beginning, and we hugged each other," he told Variety of the COVID-19-themed episodes. "It was really for us to get the message out there to wear a mask, take care of yourself."

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.

Family is important for a lot of celebrities, but they do not all prioritize their family when it comes to making career decisions. For the ones who want to be with their kids as much as possible, a job's location, daily schedule, and the duration of the shoot are all prime factors that must be considered. Patrick Dempsey learned this during his time on "Grey's Anatomy," and he has since only chosen projects that work for his entire family. "For me, from now on, I don't want to be gone longer than a week because I think that's just too much. [I've become] careful with what [I] choose to do," he told Haute Living in 2016, a year after departing "Grey's." By his own account, Dempsey is a hands-on dad who gets a kick out of the simple things like coaching soccer and driving his kids to school.

Filming location is one of the things Dempsey paid attention to when his kids were younger. When his projects were being shot overseas, Dempsey made sure they aligned with his family members' schedules so that they could accompany him. For instance, the whole Dempsey clan set up shop in London when the actor was making "Bridget Jones's Baby," and they joined the patriarch in Rome while he was filming the television series "Devils." For "Disenchanted," Dempsey not only took his family with him to Ireland, but European protocols during COVID-19 ensured that he worked a maximum of 10 hours a day — which sounds exhausting but, for actors, is actually a breeze.

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."

Patrick Dempsey stopped racing competitively in 2015 in hopes of devoting more time to his family and acting career. He stopped racing the same year that he left "Grey's Anatomy," and soon after both his reconciliation with his wife and his second-place finish at Le Mans. "My motorsports journey has been a rewarding one and allowed me to meet so many interesting people. I have loved being part of different teams and sharing the experience with so many great friends," he said in a statement at the time (via Motorsport.com). "Life has taught me that it is impossible to predict the future. I am excited to see what kind of journey I can make and enjoy."

Dempsey has remained active in the racing world, most visibly as a team owner. He co-owns Dempsey-Proton Racing and travels with the team, both domestically and to European nations, but is not bound by the same time commitment as when he was racing himself. As a seasoned racer, Dempsey has said he appreciates the ability to mentor and support up-and-coming talent. "I try to support the drivers in any way I can, I understand what they're going through, I know where they're at..." he told Porsche Sport. "The young guys, I just want to give them confidence and make them feel and let them just remember the belief in themselves and forget about this or that. So that means a lot to me and I love it."

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.

We are not sure where he finds the time, but somewhere in between acting and racing and his non-profit (and, you know, life) Patrick Dempsey founded a production company. The company has a car-themed name, Shifting Gears Entertainment, and Dempsey has used it to focus largely on his vehicular interest. There has been some non-car content — such as the film "Flypaper" and the miniseries "The Truth About the Harry Quebert Affair," both starring Dempsey, or the cycling documentary, "The Peloton Project," which taps into another of Dempsey's big passions — but most of the work the company has produced has been related to racing. For example, the company produced the Milo Ventimiglia film "The Art of Racing in the Rain" in 2019. Also, it helped make "Hurley," a film about gay racing legend Hurley Haywood's experiences as a closeted racer in the 1970s.

One of Shifting Gears' other projects, "Patrick Dempsey: Racing Le Mans," was a four-part docuseries that followed Dempsey over the course of 15 months as he fundraised, prepared for, and competed in the 24 Hours of Le Mans in France. Dempsey was also said to be working on a Formula One-focused TV series called "The Limit" at one point — centered on racer Denise McCluggage — but that never materialized. The actor has plenty of other racing stories he wants to develop for the screen as well, including a project based upon Wolfgang von Trips, whose Ferrari accident killed him and 15 others at the 1961 Grand Prix in Monza, Italy.

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.

At one point in his life, when his career had slowed and he had not yet become "Grey's Anatomy"-level famous, Patrick Dempsey made money by flipping homes in the Los Angeles area. According to an article in Men's Journal, the interior design and architecture enthusiast would work on five homes at a time and then resell them once they were fixed up. He even did a lot of the work himself, such as tiling. "I've always had an eye for good bones," he said. "I like the idea of being a caretaker for a while, then moving on. I believe in leaving a place better than you found it." Though he no longer flips homes, this mentality is very much alive in how Dempsey approaches his living spaces today.

Dempsey currently has three homes, each in a very different part of the United States, and each decorated and designed per their location. His Malibu home is the family's main residence and as of March 2023, is under renovation. The clan also have a place in Utah and another in Maine, which is older and more traditional and the one that needed the most restoration. All three homes are quite different, for good reason. "I think a midcentury modern in California really works," Dempsey explained to Architectural Digest. "Maine is a stone home, which is very practical because of the environment. And then in the mountains, it's like a ski chalet, and it was fun to redo the interior on that."