The Simpsons' Dan Castellaneta Drew Major Inspiration From Jack Lemmon's Shelley Levene For Gil

Actor Dan Castellaneta has won several Emmy awards for voicing numerous characters on "The Simpsons," and one of those well-crafted personalities is Gil Gunderson. While many have most assuredly enjoyed watching him fail humorously almost every time the unsuccessful businessman enters the frame, many may not realize that the recurring side character is based on Jack Lemmon's character from "Glengarry Glen Ross."

For those that don't know, Gil Gunderson first arrived in Season 9, Episode 9 ("Realty Bites"), where he played a struggling realtor working alongside Marge Simpson (Julie Kavner) when she decided to get into the real estate game. Poor Gil was desperate for leads, terrified of his coworker Cookie Kwan (Tress MacNeille), and his poor performance resulted in the confiscation of the cubicle wall he brought from home. After that, things continue to go bad for the character, who always seems to have the "wolves" at his door. Whether he is living in a hot air balloon, using a rotary cellphone, making payments on a broken hot plate, or just plain failing, it's pretty clear the character's entire existence is pretty messed up.

Out of all the long-running gags on "The Simpsons," one that many people would arguably agree would make a fine addition to the list would be the constant glimpses into the trials and tribulations of poor old Gil Gunderson. The character's turmoil starts to make a lot more sense when one takes into account which movie persona Castellaneta utilized to help cultivate the ill-fated character.

Dan Castellaneta has played several troubled characters on "The Simpsons" like Groundskeeper Willie and Hans Moleman, but the top candidate for most hopeless could certainly go to Gil Gunderson, who, according to the talented voice actor, was influenced by actor Jack Lemmon's character Shelly "The Machine" Levene in the 1992 motion picture "Glengarry Glen Ross." 

"There is guy Gil who is a salesman, which is just based on Jack Lemmon who is one of my favorite actors, an actor I aspire to be like," Castellaneta said during the Archive of American Television interview (via FoundationINTERVIEWS on YouTube). He went on to say that they did an entry "about real estate. It was sort of a Glengarry Glen Ross where Marge was working for real estate. And there was a guy named Gil, a very desperate, sweaty guy, so I just based him on the Shelly 'The Machine' character that Jack Lemmon played."

And while Gil may not be the most noteworthy character on "The Simpsons," Castellaneta's approach to the persona has resonated well with fans. When the question was brought up on Reddit if Mr. Gunderson was anyone's favorite, a few followers made their voices heard in support of the failure-prone personality. One user affectionately posted, "Gil is always great," and u/Plow_King also praised Gil's glory, writing, "I always wanna see ol' Gil close the deal or get a break. Love him."

Gil may not be a successful individual on "The Simpsons," but some fans agree that the Castellaneta-voiced character inspired by Shelley "The Machine" is a winner in their eyes for a variety of hilarious reasons.