6. Hans Moleman
First appearance: “Principal Charming” (Season 2, Episode 14)
Notable appearance: “A Star Is Burns” (Season 6, Episode 18)
Voiced by: Dan Castellaneta
It’s not easy being Hans Moleman. Over the the course of the series, he's been killed multiple times (only to return in a later episode), pelted in the groin with a football all for the sake of cinema, and kissed repeatedly by Homer, who claims he tastes like a peanut. He may have started out as a forgettable background character, but we've grown to love watching his misfortunes unfold in front of us like a grisly car wreck. Though he has the body of an 80 year old, Hans is actually 31, but a lifetime of severe alcoholism has transformed him into a shriveled mess of sadness.