Ol' Gil, or just Gil (maybe his full name is Gil Chesterton), voiced by Dan Castellaneta, is loosely based on Jack Lemmon's portrayal of Shelley Levene in the film version of Glengarry Glen Ross: a nervous, middle-aged man with the inability to hold a steady job due to strings of misfortunes that tend to hit him at the worst times. He has been seen holding any number of jobs, first as a real estate agent in the episode "Realty Bites", but also as a used car salesman, doorbell salesman, Coleco computer salesman, bank teller, newspaper subscription salesman, corn farmer, Kwik-E-Mart clerk, and a door-to-door salesman, selling suckless vacuum cleaners and Rick James Bibles. Since the departure of Lionel Hutz from the series, Gil has filled the role of cheap lawyer. Gil frequently refers to himself in the third person ("C'mon, help ol' Gil out here!").

At one point, at least, Gil has been married; in the episode "Marge Simpson in: "Screaming Yellow Honkers"", he mentions that his wife will leave him if he doesn't start "bringing in the green." Later in the same episode, he telephones his wife and overhears her carousing with his friend Fred. She then asks Gil if he would like to speak to Fred.

Later, in "Old Yeller Belly", Gil apparently lived at the Springfield Men's Mission (a hostel for down-and-outs), although he was forceably ejected from the premises because he had overstayed the "6 month occupancy limit." A defiant Gil walked straight into a shady organ donation clinic to sell his eyes for cash. In another episode, it is implied that Gil lives in a hot-air balloon, which is stolen by Homer and Marge Simpson. Gil's lone possession in the balloon is a hot plate.

Gil has not always been entirely unsuccessful in life. He found some brief success as a lawyer, assisting Marge with her anti-sugar campaign in Sweets and Sour Marge. He returned to the legal profession in The Frying Game, but he was less successful, as Homer and Marge went to prison.

The episode "'Tis The Fifteenth Season" includes a brief scene showing Gil attempting suicide by hanging himself with Christmas lights. He appears later in the same episode ice skating at Homer's house with the Christmas lights around his neck, suggesting that he failed yet again.

In another dead-end job, Gil works as a basketball mascot. The costume he wears is that of a basketball with very shapely, feminine legs and high heels. He dances around, Moe then proposes to him. When his costume falls off, Moe then requests he put the costume back on and be a girl for "a little longer." When Gil asks for how much longer, Moe replies "For the rest of our lives."

In Treehouse of Horror XIII, Gil seems to own a successful farm containing a large field of corn, but the many clones of Homer eat all of the corn. The clones then proceed to eat all of the flesh off of Gil's body, obviously killing him, but this obviously doesn't affect the normal storyline of the show.

He can be compared to Kirk Van Houten due to his bad luck, bad love life and frequent unemployment. He probably will have a large role in the episodes Kill Gil, parts 1 and 2. Most of his misfortunes are caused by Homer, so Homer might kill Gil.

In The Simpsons Hit & Run he sells 2 cars in one stage.

Category:Simpsons characters
Category:Fictional American television characters