Show: The Simpsons
Year: 1992 (Episode 17, season 3)
Cameo role: Himself

This episode (“Homer at Bat”) boasts a series of athlete guest stars, including Darryl Strawberry, Roger Clemens, and Mike Scioscia, but Don Mattingly takes the cake for the most memorable participation. A haircut ridiculous enough that results in Mattingly getting cut from Mr. Burns’s softball team? Only on The Simpsons.