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He followed this with another tour, Brighton Beach Memoirs, in the lead role, which was directed by Gene Saks.
Dempsey has also made notable appearances in the stage productions of On Golden Pond, with the Maine Acting Company, and as Timmy (the Martin Sheen role) in a 1990 Off-Broadway revival of The Subject Was Roses co-starring with John Mahoney and Dana Ivey at the Roundabout Theatre in New York.
In the 1990s, he mostly appeared in smaller roles in film, such as Outbreak (1995), and television, before landing a lead role in Sweet Home Alabama (2002), a surprise box office hit.
He has since then starred in a number of other films, including Enchanted (2007), Made of Honor (2008), Valentine's Day (2010), Flypaper (2011), Freedom Writers (2007), Transformers: Dark of the Moon (2011) and Bridget Jones's Baby (2016).
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.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.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.