First appearance: “Realty Bites” (Season 9, Episode 9)
Notable appearance: “Natural Born Kissers” (Season 9, Episode 12)
Voiced by: Dan Castellaneta

In a town full of drunks, losers, criminals and deadbeats, Gil Gunderson outshines them all as the lowliest citizen Springfield has to offer. First appearing as a co-worker at the real estate agency where Marge worked at in “Realty Bites,” Gil now slinks from job to job across various episodes, including a used car dealer, mall Santa, and farmer.

Frequently referring to himself in the third person as "Ol’ Gil," Gil is usually shown right before some unspeakable horror is about to befall him. We's seen him shot, forced to dance for nickels, and seemingly killed in a car accident. However, fate has a way of sparing his life just so he can live to see the humiliation of another day.