5. Gil Gunderson
Like Hans Moleman, Gil Gunsderson, who has probably had every single job in Springfield, and flourished at precisely none of them, is one of the show's great losers, inspiring affection thanks to his ludicrously tragic condition and the circumstances he invariably finds himself in. Presumably, Gil is remarkably cool at the interview stage, since he has been able to convince employers to give him high-pressure jobs in real estate and car sales, among his many occupational ventures, despite his obvious unsuitability and lack of any luck. He is the archetypal hang-dog, a loser pitied by the most tragic losers, but still cheerfully grasping at the slightest of straws that make his life more tolerable. Though he seems aware of his desperate situation, it never gets the better of him until a festive episode that sees a suicide attempt (though even then he fails, and is later seen cheerfully ice-skating with his Christmas lights noose still around his neck.) Part of his appeal, of course comes from the fact that your life will never be as sad or as close to ruin as his.
Selected Quote: "Now, let's talk rust-proofing. These Colecos'll rust up on ya' like that, er ... shut up, Gil. Close the dea... close the deal!"