9. Gil Gunderson
Springfield is known for being home to some deadbeats, but Gil Gunderson is without a shadow of a doubt the most tragic, beaten down and unfortunate character in the entire show.
He first appears as a co-worker of Marge Simpson, and even finds himself living in the Simpsons' household for an inappropriately long time before being kicked to the curb.
Seemingly upbeat and surprisingly optimistic given the state of his life, Gil has served as the show's recurring man of tragedy. Seen floating from job to job since his debut, Gil has worked, it seems, in every job the city has to offer, and along the way has been shot, fired repeatedly, ridiculed, crippled and even killed.
No matter what happens to him, though, he always reappears, once more optimistic and ready to face life, only for life to continue to torture him simply for existing.
Ol' Gil might be unlucky, but in his torment he's also hysterical.