It's hard to fathom the transition of the young Patrick Dempsey we saw playing a nerd in Can t Buy Me Love to the adult we now see playing a doctor nicknamed McDreamy in Grey's Anatomy. Exactly how this transition took place is unclear; however, the road from one to the other was anything but smooth for Dempsey.Dempsey was born on January 13, 1966, in Lewiston, Maine , and was the youngest in the family. He was a talented juggler as a teen, and came in second place at the National Juggling Competition. Attending St. Dominic Regional High School where his mother worked as a secretary, he dropped out before graduation. He was quickly discovered by an agent, and performed on stage in Torch Song Trilogy, Brighton Beach Memoirs, On Golden Pond, and The Subject Was Roses.After a handful of small roles in films and the televised version of the movie Fast Times at Ridgemont High (also starring Sean Penn and Jennifer Jason Leigh), Dempsey finally got his big break, as he starred in Can t Buy Me Love. Also starring Amanda Peterson, the movie is about a nerdy high school boy who buys the affections of the most popular girl in school to boost his own popularity. He next starred in In the Mood, the true story of a teenage boy having affairs with two younger women. The theme continued as Dempsey had the title role in Loverboy, about a pizza delivery guy that has affairs with the women at the door when making deliveries. One of his older women co-stars is Kirstie Alley.Life imitated art as Dempsey was only twenty-one, but married Rocky Parker, who was fourty-eight and had a son only one year older than Dempsey. It seems all Hollywood knew to do with him were those same type of roles, and as he got older, they didn t work out too well. He continued to work steadily, but certainly wasn t in the forefront. Of the few hits he had during this time, Mobster was one, as he starred with Christian Slater and Richard Grieco. He also starred as the title character in J.F.K.: Reckless Youth, and in With Honors with Brendan Fraser and Joe Pesci. Another starring role was in a TV remake of 20,000 Leagues Under the Sea with Michael Caine.Divorced from Parker, but remaining best friends with her son, things started to pick up for Dempsey. After starring in Scream 3, he had a reoccurring role on Will and Grace as Will's boyfriend, a sportscaster who was still in the closet about his sexuality. He moved from TV comedy to TV drama, playing the psychologically unbalanced brother to Sela Ward in Once Again, and was nominated for an Emmy for the role. He followed this with a co-starring role in Sweet Home Alabama alongside Reese Witherspoon, and also appeared in the HBO drama Iron Jawed Angels with Hilary Swank and Angelica Huston.Dempsey married for the second time, to makeup artist Jill Fink, and together they have a daughter. It seems with his latest project, Hollywood has finally figured out what to do with him. Instead of being Loverboy, his character in Grey's Anatomy, Dr. Derek Shepherd, has been nicknamed McDreamy, as he romances the intern played by Ellen Pompeo on the show. A big fan of car racing, Dempsey co-owns an Indycar team, and in his spare time, has participated in a few races.

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