From 1992 to 1993 he starred as Russell on the television series Shaky Ground. Sylvester starred as Col. John Henchy in the TV series The Army Show in 1998 and as Wendell Loman in the series City of Angels in 2000. He has starred in several films including An Officer and a Gentleman, Uncommon Valor, Vision Quest, and Corrina, Corrina. In 2001 he won a Sports Emmy Award for Outstanding Sports Documentary for On Hallowed Ground: Streetball Champions of Rucker Park.
