Patrick Dempsey rose to fame for his iconic role as Derek "McDreamy" Shepherd, the charming neurosurgeon with flawless locks, on the hit TV show Grey's Anatomy. Despite this breakthrough, Dempsey's career had already commenced two decades prior to the debut of the medical drama. In fact, at a mere age of 21, he secured his first significant role in the 1987 movie In the Mood. In the film, Dempsey brilliantly portrayed the notorious Sonny Wisecarver, an American teenager who gained notoriety in the 1940s for his scandalous relationships with older women.
Throughout the years, the actor ventured into portraying various captivating and central male characters. However, despite Dempsey being regarded as one of Hollywood's most attractive personalities, he wasn't always perceived as "McDreamy" by his colleagues.
Opening up during a Nightline interview in 2016, Dempsey disclosed, "During my childhood, I was rather petite and consequently was labeled 'the amoeba.' This was the nickname I had. It wasn't your typical nickname. Nonetheless, I experienced a delayed growth spurt."
Keep scrolling for a look back at Dempsey’s life and career over the years:
Credit: Daniele Venturelli/WireImage
Patrick Dempsey Through the Years: ‘Grey’s Anatomy,’ Movies, Marriages and More
Patrick Dempsey gained fame for his notable performance as Derek "McDreamy" Shepherd, a neurosurgeon with impeccable hair, on the popular TV show Grey's Anatomy. Nevertheless, Dempsey's professional journey commenced twenty years prior to the release of this medical drama. At the age of 21, he landed a significant role in the film In the Mood (1987), portraying the true-life character of Sonny Wisecarver, a young American who gained notoriety in the 1940s for his romantic involvements with older women.
In his film career, the actor proceeded to portray a multitude of heartthrobs and leading men. Despite his esteemed image as one of Hollywood's most attractive celebrities, Dempsey wasn't always regarded as "McDreamy" by his fellow peers.
"During my upbringing, I was actually quite petite so I was affectionately called 'the amoeba.' That was the nickname I had," Dempsey revealed in a 2016 interview on Nightline. "It definitely wasn't your typical nickname, but I went through a growth spurt later on."
Keep scrolling for a look back at Dempsey’s life and career over the years:
Credit: Cover Images
1987
Dempsey paid tribute to his former costar, Amanda Peterson, on X (formerly Twitter), following her untimely death at age 43 in 2015. Expressing his condolences, Dempsey wrote, "She will always be remembered as vibrant and young. Gone too soon. My thoughts and prayers go out to Amanda's family."
Dempsey tied the knot with Rochelle “Rocky” Parker, his first wife, in 1987, at the age of 21, while Parker was 48. Prior to their romantic involvement, Parker served as Dempsey’s manager and acting coach.
Credit: Frank Trapper/Corbis via Getty Images
1994
Dempsey and Parker ended their marriage after being together for almost seven years. In a 2006 interview with Barbara Walters, Dempsey discussed the significant age difference between himself and Parker.
"I believe I was seeking a maternal figure," expressed the actor from Sweet Home Alabama. "There have been numerous negative aspects that I am still working through because of it."
Parker died at age 74 in 2014.
Credit: Steve Granitz/WireImage
1999
Dempsey married makeup artist Jillian Fink after two years of dating. They later became parents to daughter Talula in 2002 and twin sons Darby and Sullivan in 2007.
In a 2019 interview with Entertainment Tonight, Dempsey confessed that his children are not impressed by his heartthrob reputation. "They tease me," he revealed. "They remind me not to take myself too seriously."
Credit: Gregg DeGuire/WireImage
2001
The Made of Honor star received an Emmy nomination for Outstanding Guest Actor in a Drama Series for his role as Aaron Brooks in the ABC family drama series Once and Again.
Credit: Devan/INFGoff.com
2005
Viewers were first introduced to Dr. Derek Shepherd in March when Grey's Anatomy premiered. Over the course of the next 11 seasons, Dempsey's portrayal of the character and his onscreen romance with Ellen Pompeo as Meredith Grey captivated audiences.
Their onscreen chemistry was so intense that Pompeo's real-life husband, Chris Ivery, found it difficult to watch their intimate scenes.
“I recall how challenging it was for [Chris] initially,” Pompeo revealed on the “Ladies First With Laura Brown” podcast in 2020. “He expressed his discontent, stating that this was not what he had envisioned. You go to your workplace and engage in intimate scenes with him. I appreciate Patrick and think he's a great guy, but seriously?”
Credit: Cover Images
2007
Dempsey played divorce attorney Robert Philip in the musical movie Enchanted, which launched his costar Amy Adams to superstardom.
Credit: Charley Gallay/Getty Images for Porsche Design
2015
Fink initiated divorce proceedings in January after being married for 15 years, but they ultimately reconciled later that same year. Their divorce was called off in November 2016. In a November 2022 interview with Fatherly, Dempsey credited therapy for helping him and Fink find their way back together.
"It is crucial to engage in individual therapy, followed by couples therapy," he emphasized. "Through my experience, I have come to realize that being in a therapist's office allows me to perceive things differently as there is a level of emotional detachment. This setting provides the necessary room and space for me to sincerely comprehend your perspective and emotions. I genuinely do not want you to feel that way and I am committed to resolving and improving this issue together."
Credit: Karwai Tang/WireImage
2015
After 11 seasons, Dempsey made the decision to depart from Grey's Anatomy following his character's demise in an April episode. He expressed his thoughts on the matter, stating that Shepherd was a well-loved character and acknowledging the uncertainty surrounding the audience's reaction.
Credit: INFphoto.com/Instar Images
2021
After retiring from his medical career, Dempsey made a comeback to Grey's Anatomy in season 17 as a recurring character. Throughout the season, his character made multiple appearances to Meredith, who was in a coma as a result of COVID-19 complications.
Pompeo shared in an interview with Deadline in November 2020 that her connection with Patrick felt timeless, as if they had been longtime friends since their first meeting. Working together again felt natural and effortless, and their chemistry and camaraderie have always been beneficial to their performances. She also expressed a genuine fondness for him.
Dempsey, on the other hand, expressed in an interview with Variety in April 2021 that he viewed his return to the show as a beautiful ending to Derek and Meredith's love story.
"Their status as an iconic couple led us to aim for a message of hope, considering the numerous losses we have experienced this year. In a world as gloomy as the one we currently inhabit, the idea of celestial beings watching over and caring for us is a reassuring one," he expressed to the outlet. "Thus, for all of us, this conclusion to the story was truly beautiful. I am immensely grateful for participating in it and delighted by the overwhelming positive response from fans."
Credit: Moviestore Collection/Cover Images
2022
Dempsey and Adams both reprised their roles in the Enchanted sequel, Disenchanted, which premiered on Disney+ in December. In this follow-up film, Dempsey had the opportunity to showcase his singing skills, which he did not do in the original installment.
Reflecting on the experience, Dempsey expressed his joy during the process of discovering his singing voice, working with a vocal coach, and learning the lyrics and dance routines. He described it as an extraordinary and unfamiliar experience. Speaking to the website Ashley & Company in November 2022, he explained the captivating sensation of singing and the intoxicating effect it had on him. Being able to immerse himself in the fairy tale world for a period of time was also a delightful experience for him.
Credit: Elisabetta A. Villa/Getty Images
2023
Dempsey was named People’s 2023 Sexiest Man Alive in November after previously ranking second on the outlet’s “Sexiest Men Alive” list in both 2005 and 2006.