Character: Gil Gunderson, voiced by Dan Castellaneta
First Episode: Realty Bites (S09, E09-187)
Occupation: It varies from episode to episode, suffice it to say whatever job he has in an episode, he doesn't hold it for long.
General Demeanor
Sometimes referred to as "Ol' Gil", often by himself, Gil is an aging, overbearing man whose desperation to succeed does not match his actual capability to do so. Now, there are instances where he does succeed, but regardless he's in a different job in each episode he appears in. In most of these episodes, Gil attempts his hardest to perform his job, but often does so incompetently. That said, Gil does have a good work ethic and he does try his hardest at whatever he tries to do; but it hardly ever works out for him.
Unintentionally, Gil's debut episode, Realty Bites, was also the final episode to feature the incompetent lawyer-turned real estate agent Lionel Hutz before Phil Hartman passed away and the character was subsequently retired. As a result, some fans have considered Gil a sort of spiritual successor to Hutz, especially since there has been a couple of episodes where the Simpson family hired Gil to defend them in court. Of course, Gil and Hutz aren't really the same character at all; while Hutz was brash and reckless in his incompetence, Gil is far more meek and bumbling in his.
Key Character Moments
As a Season 9 debut character, Gil of course has no moments in the more memorable seasons of the show. Given that newer seasons have been so awful at creating new, lasting characters, Gil remains one of the "newer" recurring characters in the series despite debuting 17 seasons ago now.
The Fall of the Simpsons
In Realty Bites, Gil is a real estate agent who is likely nearing his end with the company. Lionel Hutz constantly threatens Gil to turn it around or lose even more walls to his cubicle. If it wasn't for Marge's major screw up late in the episode, he probably would've been next on the chopping block. He probably got it, anyway.
Gil pops up again in the Season 9 finale Natural Born Kissers as a used car salesman, whose hot-air balloon home is stolen by a naked Homer and Marge, tossing out a hot plate he had nearly paid in full. Gil is again selling cars in Season 10's Marge Simpson in: "Screaming Yellow Honkers", but has a sale usurped from him with him putting up little resistance. In between, he successfully sells Coleco computers to the Springfield school district in Lisa Gets an "A".
Zombie Simpsons
In two Season 13 episodes, Gil acts as the Simpson family lawyer. The first, Sweets and Sour Marge, he successfully helps Marge ban sugar in Springfield, for a time anyway. Later, in The Frying Game, Gil in unsuccessful in defending Homer and Marge from murder charges, though it was later revealed to be a setup for a reality show. I doubt Gil was aware.
To date, there remains one single episode to focus entirely on Gil Gunderson: Season 18's Kill Gil, Volumes I & II. In it, Gil is once again fired, this time as a mall Santa. Marge feels sorry for him as it was because he was caught giving a toy reserved for his boss to Lisa, and lets him stay with the Simpsons until he got back on his feet. Almost a year passes, however, and Gil still hasn't left. Marge finally builds up the anger to yell at Gil, but then she learns Gil actually found a job and left Springfield. Unwilling to let that pent up rage subside, Marge finds Gil in Arizona and finally lets him have it, but the scene causes Gil to be fired again. To make up for it, the family buys a house in Arizona and spends Christmas with Gil once more.
Season 20's Homer and Lisa Exchange Cross Words has Lisa competing in a crossword puzzle tournament. Lisa makes it to the finals against Gil, and Gil ends up winning after Lisa chokes it near the end.
Zombie Simpsons HD
Gil's appearances since has been mostly cameos or gags. He makes one notable appearance in Season 26's Super Franchise Me, hired by Marge to help run her new sandwich shop, but is fired for incompetence.
Gil is the least popular, least fleshed out character I've done a spotlight on thus far, so the opportunities to really see Gil "shine" are limited.
(Not really) Must Watch Episodes that Focus on Gil Gunderson
Realty Bites
Kill Gil, Volumes I & II
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