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He participated in this series as often as his schedule allowed, although insurance restrictions kept him from driving competitively while also filming a motion picture.

In 2009, he raced a Team Seattle Advanced Engineering Ferrari F430 GT in the 2009 24 Hours of Le Mans's GT2 class and finished ninth in class.

He followed this with another tour, Brighton Beach Memoirs, in the lead role, which was directed by Gene Saks.

Prior to landing the role, Dempsey auditioned for the role of Dr. He also appeared in two episodes of the Grey's spinoff Private Practice, playing the same character.

Dempsey was nominated for Best Performance by an Actor in a Television Series–Drama at the 2006 Golden Globes for the role.

"I have never given up." Dempsey was discovered by an invitation to audition for a role in the stage production of Torch Song Trilogy.

His audition was successful, and he spent the following four months touring with the company in Philadelphia.

Dempsey made a number of featured appearances in television in the 1990s; he was cast several times in pilots that were not picked up for a full season, including lead roles in the TV versions of the films The Player and About A Boy.

However, he received good reviews as he portrayed real-life mob boss, Meyer Lansky in 1991 when Mobsters was put on the screen.

Dempsey's first major feature film role was at age 21 with Beverly D'Angelo in the movie In The Mood, the true World War II story about Ellsworth Wisecarver whose relationships with older married women created a national uproar.

He then co-starred in the third installment of the comedy classic Meatballs III: Summer Job, alongside Sally Kellerman in 1987.

This was followed by the teen comedy Can't Buy Me Love in 1987 with actress Amanda Peterson and Some Girls with Jennifer Connelly in 1988.

In 1989, Dempsey had the lead role in the films Loverboy with actress Kirstie Alley and Happy Together with actress Helen Slater.

Dempsey received an Emmy nomination in 2001 as Outstanding Guest Actor in a Drama Series for the role of Aaron. Kennedy in the two-part TV mini-series JFK: Reckless Youth. Dempsey had a high-profile role as the fiancé of Reese Witherspoon's character in Sweet Home Alabama (2002).

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