First appearance: “Homer’s Phobia” (Season 8, Episode 15)
Voiced by: John Waters 

Leave it to The Simpsons to be one of the first American TV shows to tackle the topic of homosexuality head-on by introducing the character of John, aptly voiced by John Waters, in the episode “Homer’s Phobia.” Much of the characters strength comes from Waters, who obviously had a vested interest in turning John into one of the great Simpsons one-off characters ever. 

Waters manages to bring his singular personality to the voice acting in this role; the animators and writers simply had to keep up with his performance and ad-libs. Best of all, Waters and the show’s crew managed to make John fit seamlessly into the Springfield universe without his character ever getting too preachy about the serious, real world themes.