4. Michael Jackson As Leon Kompowsky In "Stark Raving Dad"
When Homer is committed to a mental institution (for wearing a pink shirt to work), he meets "Michael Jackson" -- or a 300-pound, bald, white patient who thinks he is (and sounds just like) the King of Pop. Homer, having never heard of Jackson, takes the man at his word, but when he brings his new friend home, Bart -- who promised friends Jackson would be appearing at his house -- is a laughingstock. Luckily, "Michael" manages to help Bart compose a birthday song for Lisa, winning their affection in the process. The appearance of Jackson -- who was credited as "John Jay Smith" -- may have ranked higher, but the actual King of Pop only voiced his character during spoken lines -- he used an impersonator for the songs. Still, it was a feel-good episode from an era where The Simpsons mastered the art. Reportedly a sequel was planned in which Kompowsky returns, this time impersonating Prince, but scriptwriters and Prince couldn't come to terms.
Best line: "Bubbles, it's going to be a long night."