Cheadle became eligible for his Screen Actors Guild (SAG) card when he appeared as a burger joint employee in the 1985 comedy "Moving Violations". In 1987 he received a small role in episode 19, season 7 of "Hill Street Blues" where he played a teenager with learning difficulties. Followed by an appearance in "Hamburger Hill" the same year; Cheadle secured the role of Jack in the April 1, 1988, "Jung and the Restless" episode of "Night Court". Although his character was 16 years old, Cheadle was 23 at the time.