Matt Groening’s crowning achievement, The Simpsons, began its life as a series of animated shorts on The Tracey Ullman Show that focused only on the titular family. When these shorts proved to be popular enough to make the leap to a half-hour primetime timeslot, Groening expanded the world that the characters inhabit.
Inspired by the sketch comedy series Second City Television, Groening decided to populate Springfield with a huge cast of supporting characters. From the religious zealot next door to the evil billionaire who owns the nuclear plant, there are a ton of hilarious secondary characters in the Simpsons universe.
Mayor Quimby
Conceived as a satirical caricature of John F. Kennedy, “Diamond” Joe Quimby is the unscrupulous politician who has managed to be the Mayor of Springfield throughout the series’ entire three-decade run.
Despite the many bribes that he accepts, the many extramarital affairs that have been exposed, and the many public blunders he’s made while in office, the guy keeps getting re-elected. He doesn’t even bother to hide his immoral practices anymore.
Troy McClure
You may remember Troy McClure from such films as Dial M for Murderousness, The Erotic Adventures of Hercules, and The Wackiest Covered Wagon in the West. He appears on the show in PSAs he’s done as well as in his personal life as a washed-up actor.
When voice actor Phil Hartman died, it was a tragedy for many reasons, one of which being that the show had to retire his hysterical characters.
Dr. Hibbert
There are two doctors in the Simpsons universe: Dr. Hibbert, who's a reputable professional and charges accordingly, and Dr. Riviera, who doesn’t fully understand the human anatomy but works on the cheap.
The latter’s malpractice has been used for comedy gold, but it’s the former who’s been responsible for the most laughs, from his iconic chuckle to his groundbreaking “jiggle test.”
Lionel Hutz
Another role played by the great Phil Hartman, Lionel Hutz is a hilariously unqualified attorney. He is to the law what Dr. Nick Riviera is to the medical profession. He prepares for each trial by watching episodes of Matlock in a bar.
His business card says, “Works on contingency, no money down,” but he corrects it with a little punctuation: “Works on contingency? No, money down!”
Ralph Wiggum
Whether he’s having his heart broken by Lisa or running for the office of President of the United States, Chief Wiggum’s eccentric son Ralph is a lovable icon.
Ralph has uttered a ton of hilarious lines over the course of the show’s run: “Me fail English? That’s unpossible,” “I bent my Wookiee,” “Hi, Super Nintendo Chalmers,” and “My grandma had hair like that when she went to sleep in her forever box.”
Krusty The Clown
Krusty the Clown was originally conceived to be the double life of Homer Simpson. The joke would be that Bart’s hero turned out to be his father, whom he didn’t respect.
This twist was scrapped when Krusty developed into a character of his own, a satirical jab at washed-up comics who steal jokes and sold out a long time ago.
Moe
In the early seasons of The Simpsons, Moe was just the target of Bart’s prank calls, but as the series has gone on, the local bartender has developed into a more rounded, relatable character. He suffers from terrible depression, which has allowed for dramatic moments as well as comedic ones.
The shady activities he gets up to in the back room of his bar (involving everything from pandas to killer whales), not to mention his complicated, vaguely defined past, have led to many terrific gags.
Ned Flanders
The annoying neighbor is one of the most overused tropes in TV comedy, but Ned Flanders is hilarious and unique. What makes him “annoying” is that he’s annoyingly nice as a result of his unwavering religious faith.
Although Flanders’ beliefs are the source of plenty of great gags, he shines the best when he’s forced to team up with Homer. They’re one of the show’s most lovable double acts.
Principal Skinner
From his Oedipal relationship with his mother to his desperate attempts to please Superintendent Chalmers to his rivalry with Bart to his flashbacks to his time in ‘Nam, Principal Skinner is always a delight.
The only downside to the character is that the show intentionally sabotaged him. In the controversial episode “The Principal and the Pauper,” which Harry Shearer himself objected to, Skinner is revealed to be an impostor. It was a slap in the face to all the Simpsons fans who’d come to adore the character over the years.
Milhouse
Bart’s dorky best friend is sort of the Sancho Panza to his Don Quixote. Milhouse would follow Bart to the ends of the earth. In addition to being Bart’s pal (even when Bart rejects him), Milhouse has a futile crush on Lisa, so he’s pretty embedded in the Simpson clan.
His most memorable moments include: being turned down as an heir by Mr. Burns (“But my mom says I’m cool!”), trying out his flood pants (“Everything’s coming up Milhouse!”), and petting a terrifying sea creature after losing his glasses (“Nice doggy!”).