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In 1981 he achieved the second place at the International Jugglers' Association Championship in the Juniors category, just behind Anthony Gatto, who is considered to be the best technical juggler of all time. He told Barbara Walters on her 2008 Oscar special that he thinks dyslexia made him what he is today.
"It's given me a perspective of—you have to keep working," Dempsey told Walters.
Prior to landing the role of Derek Shepherd, Dempsey auditioned for the role of Dr. Initially, a midseason replacement, Grey's Anatomy was well received and has become a highly rated program.
He then co-starred in the third installment of the comedy classic Meatballs III: Summer Job, alongside Sally Kellerman in 1987.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).