Dick was born in Charleston, South Carolina. He was adopted at birth by Allen and Sue Dick. His surname at birth was Thomlinson.

Dick graduated from Joliet West High School (Joliet, Illinois) in 1984. He was in numerous productions during high school, was well known as the class clown, and was elected homecoming king his senior year in the fall of 1983. Even in high school, Dick tended to use his name as a joke. One day while dressed in the Joliet West gold athletic sweats he pulled on a pair of red shorts over his sweats and used a red towel as a cape matching his shorts. He presented himself at school as "Super Dick." He's good friends with theatre personality Anthony Rapp, who has known him since they were children.