He performed at age nine in local events, and by age 13, had traveled the tri-state area as a clown in a regional circus. He continued to hone his craft by acting, directing and writing plays and performing a magic act at local area clubs that evolved into a stand-up comedy routine. Making the move to Los Angeles at age 21, Roebuck won stage roles in such presentations as the U.S. premiere of Sarcophagus at L.A.T.C., No Time for Sergeants and the world premiere stagings of Holy Toledo and Who Killed Orson Welles. He won praise for one of his first movie roles, the haunting, stoned-out teenage murderer, in Tim Hunter's searing drama, River's Edge. A familiar face to fans of the hit TV series Matlock, in which he played legal assistant Clifford Lewis for three seasons, Roebuck has logged roles in such telefilms as Caught in the Crossfire, Runaway Father, the small screen remake of The Dirty Dozen and The Killing Mind on Lifetime. . He also shared a small piece of television history with a role in the episode of Star Trek: The Next Generation which resurrected Leonard Nimoy's Mr. Spock and introduced the new TV series