12. Hans Moleman
Probably the most tragic figure in all of Springfield, aside from Grandpa Simpson, who seems to be presented as justifiably neglected by the show, and Gil Gunderson (more on whom later,) Hans Moleman seems to be rather unjustly abused by the writers, but with incredibly funny results. We've never really seen much of a backstory for the unfortunate old man - whose real age is revealed as 31, with his shocking appearance being down to the ravages of alcoholism - though a deleted scene did show him living in a house under the dam, and early episodes actually billed him as Hans Melish. Based on Droopy, and included as a supporting character to defy the inexplicable complaints that his appearance garnered from clearly-too-sensitive souls, the cruel, but hilarious reality for Moleman is that he is no more than a diverting running gag. The humour of his situation is that he frequently finds himself staring Death in the face, usually without a set-up to add to the impact of his ridiculous bad fortune, and though his fate always looks grimly sealed, he survives, again without so much as a thin explanation.
Select Quote: "Help me! Some bullies threw my shoes over a telephone wire... With me in them!"