He did his schooling from the Baltimore School for the Arts but did not receive his diploma.He debuted in the fields of acting on-screen with John Waters’ film Hairspray on 1988.
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They both graduated from Lakeside High School in Evans, Georgia.
Kelley attended the University of Georgia in Athens, Georgia, where he was a member of the Nu Zeta chapter of the Lambda Chi Alpha fraternity.
Following his role of Dan Rydell which won him a Screen Actors Guild Nomination, he appeared as Jake in a project called In Treatment of HBO.
The CBS drama The Good Wife, which portrayed him as Will Gardner, won him a nomination for the Primetime Emmy Award for Outstanding Supporting Actor in a Drama Series twice.