Number 27: Gil Gunderson
47 Points
(4 of 10 lists. Highest ranking #8 by Relaxing Dragon) Biography:Gil Gunderson is an unsuccessful and unlucky businessman in Springfield (and Scottsdale, AZ.)
At the age of six, Gil was hired by his eight-year-old brother to run his sidewalk lemonade stand for the afternoon. By the end of the day, he had bankrupted his brother's business and drank up all the remaining inventory. Since then, Gil has not managed to hold down one job for longer than a few days. He kept his job at Red Blazer Realty for over twenty years by selling his own house to himself several thousand times. Eventually, the house was destroyed in the Great Springfield Flood of '99, and with no other sales prospects, he was fired
Over the years, Gil has been a car salesman, real estate agent, a lawyer, an ad buyer for the local newspaper, an Amway distributor, a music manager, a bag clerk for the local supermarket, Apu's assistant at the Kwik-E-Mart, a mall Santa, a bank security guard, and handing out flyers for a strip club.
Voiced By: Dan Castellaneta
First Appearance: “Realty Bites” - Season 9, Episode 9
Notes: Gil is loosely based on Jack Lemmon's character in “Glengarry, Glen Ross.”
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