Gil Gunderson, a.k.a. Ol’ Gil, is a character on ‘The Simpsons’ voiced by Dan Castellaneta that first appeared in the ninth season episode ‘Realty Bites’ as a real estate agent with Lionel Hutz’s Red Blazer Realty. He is a spoof of actor Jack Lemmon’s portrayal of Shelley Levene in the 1992 film adaptation of the play ‘Glengarry Glen Ross.’ (Lemmon himself voiced a character similar to Levene in the eighth season episode ‘The Twisted World of Marge Simpson’). Show runner Mike Scully said that the writers thought that Gil would be ‘a one-shot thing’ ‘Dan Castellaneta was so funny at the table read doing the character,’ Scully elaborated, ‘we kept making up excuses in subsequent episodes to put him in.’
Writer Dan Greaney said that it was a great take-off on Levene to make Gil more desperate than he was. Even so, the writers like to write Gil with ‘a little bit of the old sparkle’ left in him. With the retirement of the character Lionel Hutz (after voice actor Phil Hartman’s death), Gil has been working as the Simpsons’ lawyer in later episodes. He had several jobs but inevitably fails at any endeavour, often tragically. For example, he was shot on his first day as a security guard in the bank. As revealed in ‘Natural Born Kissers,’ he lives in a balloon..
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