Since The Simpsons has been on TV for, like, a million years, and has created some legendary characters outside of the five nuclear family members of the Simpsons, it makes sense that there would be a lot of great episodes that feature these “side” characters. It’s a little weird to call them side characters, as in many ways some of these are as important as the family members. Still, these are episodes allowing other characters to shine like Marge, Homer, Lisa, Bart, or Maggie.
The Last Temptation of Krust
Krusty the Clown is one of the OG side characters. He’s been the focus of a lot of shows, but maybe the best “The Last Temptation of Krust” from Season 9. Krusty bombs on stage with his stand up act that includes jokes that were offensive in the 1940s. Krusty re-invents himself as a George Carlin-like comedian and once again reaches the pinnacle of his profession, only to sell out once again.
Who Shot Mr. Burns?
One of the greatest TV cliffhangers of all time came at the end of Season 6 with “Who Shot Mr. Burns.” Seemingly everyone in town has reason to murder the owner of the Nuclear Power Plant, and most of the episode follows Mr. Burns and his various run ins. The first episode of Seven 7, when it’s reveals who actually shot him, is mostly about him too
Flaming Moe’s
“Let’s all go to Flaming Moe’s” is the catchy jingle that every Simpsons fan is humming to themselves right now. As implied, the episode from Season 3 is all about everyone’s favorite surly bartender, Moe. Moe is forced to re-invent his bar with a drink he invents that includes being lit on fire, to the detriment of Lenny and Carl, among others. It also featured the first appearance by a band on the show when Aerosmith guest stars.
Selma’s Choice
Patty and Selma are technically family members, but they aren’t always welcome by everyone, especially Homer. “Selma’s Choice from Season 4 is about Selma deciding she doesn’t want to die alone and desires having a child. The episode also has some classic moments, like Lisa returning from Duff Gardens while “coming down” and Homer eating a giant Hoagie for days.
The Principal And The Pauper
For many, “The Principal And The Pauper” in Season 9 is the moment the show jumped the shark. There is a solid argument for it, but not because it’s about a supporting character, Principal Skinner. It’s because the episode re-writes his backstory, which is silly.
Radioactive Man
Despite the episode’s name, “Radioactive Man,” the one from Season 7 is mostly about Milhouse. Milhouse wins a role in the latest Rainier Wolfcastle’s action movie, filming in Springfield. Bart takes it hard and eventually Milhouse loses his zest for movie-making as well.
Two Dozen and One Greyhounds
“Two Dozen and One Greyhounds” is, as the name hints at, a parody of 101 Dalmatians. In the Season 6 episode, Mr. Burns decides he needs a coat made of greyhound puppies, including 25 sired by the Simpson family dog, Santa’s Little Helper.
Lady Bouvier’s Lover
Grampa Simpson is one of the most often seen supporting characters, but Marge’s mother, Jacqueline Bouvier, isn’t nearly as common. However, in a Season 5 episode called “Lady Bouvier’s Lover,” she plays a big part when she and Grampa start dating.
22 Short Films About Springfield
“22 Short Films About Springfield” is about a lot of different characters on The Simpsons who aren’t family members. It was a completely new approach to an episode when it debuted in the shows seventh season, telling, well, 22 different stories about various characters both familiar and new.
Much Apu About Nothing
Hank Azaria has been voicing Simpsons characters since the very beginning of the show. One voice he no longer voices, however, is Apu. The character was retired after it was (rightly) decided that a white guy should be the voice of an Indian character. That said, there are still some classic episodes focused on the Kwik E Mart owner, like “Much Apu About Nothing.”
Sideshow Bob Roberts
Kelsey Grammer is one of the most famous guest voices in the show’s history for his legendary character, Sideshow Bob. The murderous former sidekick to Krusty has been the focus of multiple episodes over the years, like “Sideshow Bob Roberts” when Bob runs for office (and almost wins).
Krusty Gets Kancelled
“Krusty Gets Kancelled” is the finale of Season 4 and it is, by most accounts, a true classic episode. The episode focuses on Krusty the Clown, obviously, who loses his show after his ratings tank due to a rival called “Gabbo.” Bart and Lisa team up to get Krusty’s show back on the air.
When Flanders Failed
Poor Ned Flanders. Not only does he have to live next door to the Simpsons, he often faces a lot of bad luck. In “When Flanders Failed,” Ned’s store, The Leftorium, is forced to close and the “Flanderses” fall on hard times. It ends with one of the sweetest moments between Homer and Ned, though.
Burns, Baby Burns
In Season 8, audiences learn that Monty Burns fathered a child when we meet his son Larry, voiced by the great Rodney Dangerfield. In a nod to a movie where Dangerfield had some of his most ridiculous lines, Caddyshack, when “Anyway you Want It” by Journey plays over the credits.
A Milhouse Divided
As the episode title reveals, “A Milhouse Divided” is all about Bart’s best friend and his parents. After a disastrous dinner party at the Simpson’s house, Kirk and Luanne, Milhouse’s parents, decide they are divorcing. It’s hard to believe this was in the eighth season, as it seems like they’ve always been divorced.
Homer and Apu
The 13th Episode of Season 5 is all about Apu when Homer helps to get him fired from the Kwik E Mart. It’s one of the episodes that likely led to the decision to retire the character, but it was a classic at the time.
The Otto Show
“The Otto Show” from Season 3 is…well… all about everyone’s favorite palindrome, Otto the bus driver. Otto loses his driver’s license and at first Patty and Selma aren’t interested in helping him, until it’s revealed Otto only wants to get his license back to make Homer mad.
Rosebud
“Rosebud” from Season 5 opens with a bang, when The Ramones appear to sing happy birthday to Mr. Burns. The episode focuses on Burns, even managing to, at least temporarily, make him a sympathetic character when we learn he longs for his long lost teddy bear, an analog, of course, for one of the greatest MacGuffins in film history, the sled in Citizen Kane.
Like Father, Like Clown
Krusty is Jewish, and it turns out his father is a Rabbi. And he’s a Rabbi that disowned his son many years ago. This hurts Bart and Lisa when they learn about it in the Season 3 episode “Like Father, Like Clown,” so they team up to get the two to reconcile.
Raging Abe Simpson and His Grumbling Grandson in ‘The Curse of the Flying Hellfish’
There are countless backstories about Abe Simpson and one of the wildest is told in “Raging Abe Simpson and His Grumbling Grandson in ‘The Curse of the Flying Hellfish.'” It turns out Grampa was once part of an elite fighting squad during World War II and he enlists Bart to help him recover a lost treasure in this episode from Season 7.
Hurricane Neddy
Ned Flanders is one of the chillest residents of Springfield, but he has his limits, as we see in “Hurricane Neddy” when he loses after a series of bad luck befalls the hapless neighbor of the Simpsons. His explosion at the whole town is one of the funniest moments in the show’s history in this Season 8 episode.
A Fish Called Selma
You might remember Troy McClure from his hit movies from the ’70s like ‘P is for Psycho’ and ‘The President’s Neck is Missing!’ You also might remember him as the love interest to Selma in one episode of The Simpsons from Season 7. It’s episodes like this that make us really miss Phil Hartman, who voiced the washed up star.
Two Cars in Every Garage and Three Eyes on Every Fish
Local politics has long been part of The Simpsons. Very early on, in Season 2, Mr. Burns runs for governor in “Two Cars in Every Garage and Three Eyes on Every Fish,” after Bart catches a three-eyed fish near the power plant. It all goes very wrong for the old man.
Dumbbell Indemnity
Moe has always been unlucky in love, as highlighted in Season 9 when he and Homer team up to get him a girlfriend in “Dumbbell Indemnity.” Oscar winner Helen Hunt guest stars as Moe’s girlfriend, Renee. Sadly, the relationship doesn’t last.
Brother from Another Series
While Kelsey Grammer has long guest-starred on The Simpsons, in Season 16 Grammer is joined by David Hyde Pierce who plays Bob’s brother, Cecil Terwilliger. Pierce, of course, also plays Nils Crane on Frasier, hence the title of the episode, Brother from Another Series.
Burns Verkaufen der Kraftwerk
Mr. Burns’ whole identity is wrapped up in being the owner of the power plant and therefore the most powerful man in Springfield. When he sells the plant in Season 3, it doesn’t take long for him to realize that he can’t live without the power and the fear it instills in everyone, so he has to buy it back.
The Simpsons Spin-Off Showcase
There really isn’t a more obvious example of episodes on The Simpsons about supporting characters than “The Simpsons Spin-Off Showcase.” As the name explains, it’s all about possible spin offs, including the best idea, Principal Skinner and Chief Wiggum teaming up as PIs in New Orleans. Just remember, New Orleans isn’t really a party town.
The Two Mrs. Nahasapeemapetilons
“The Two Mrs. Nahasapeemapetilons” from Season 9th Season is a wild one. There are some somewhat offensive moments with Apu and his wife Manjula, especially from Homer, but it’s a good example of the redemption of the characters at times, too.
Grade School Confidential
A truly classic episode, “Grade School Confidential” is all about Skinner and Bart’s teacher Edna Krabappel. The two end up in a relationship after they fall for each other at a party at the Simpson’s house. Even Ralph Wiggum sees them making out in a closet.
Sideshow Bob’s Last Gleaming
The PTA Disbands
Before they briefly dated in Season 8, Ms. Krabappel and Principal Skinner were furious with each other in Season 6, in the episode “The PTA Disbands.” A lot of other characters take place in this ensemble episode of the show.
Dog of Death
You never know which character is going to take center stage and it could even be the family dog, Santa’s Little Helper. In the Season 3 episode “Dog of Death,” vet bills overwhelm the family and they start to resent their lovable mutt. He ends up running away and into Mr. Burns’ arms. The evil power plant owner trains the dog to be a vicious guard dog, at least for a while, until Bart reconnects with his beloved pet.