Stevie Wonder on 'The Cosby Show' (1986)
Producers typically have to invent some kind of reason for a musician to wind up in a sitcom setting — if they have to stretch the limits of plausibility to make a cameo work, so be it. This is one of those cases: Theo (Malcolm-Jamal Warner) and Denise (Lisa Bonet) get into a minor car accident with Stevie Wonder, who offers the Cosby family a chance to visit his studio as appeasement. (Ahmir "Questlove" Thompson has gone on record saying this episode was a pivotal moment for the evolution of hip-hop, due to the fact that Wonder demonstrates how to use this new techno-gizmo called a "sampler.") The visit culminates in a group sing-along of Wonder's hit single "I Just Called To Say I Love You."