In the early seasons of The Simpsons, Principal Skinner’s storylines always revolved around his ongoing battle with his arch-nemesis, Bart. But, from his harrowing backstory in the Vietnam War to his unhealthily close relationship with his mother Agnes, the writers have since expanded Skinner’s characterization beyond his rivalry and focused entire episodes on the uptight educator.
Skinner may be at the center of one of The Simpsons’ worst episodes – season 9’s “The Principal and the Pauper,” which bafflingly revealed him to be an impostor – but he’s also been at the forefront of some of the show’s best installments.
Pranks And Greens (Season 21, Episode 6)
Principal Skinner’s backstory was detailed in the season 21 episode “Pranks and Greens,” which guest-starred Jonah Hill as Andy Hamilton, the prankster who ruled Springfield Elementary before Bart.
Groundskeeper Willie explains that Skinner used to be a fun-loving, happy-go-lucky guy until Andy trapped him in a swimming pool full of worms for an entire weekend and turned him into the stern-faced bureaucrat he is today. It’s always fun when the writers reveal new details of a well-worn character’s origin story to explain how they became the person that fans know and love.
The Otto Show (Season 3, Episode 22)
As the pun-tastic title would suggest, season 3’s “The Otto Show” primarily revolves around Otto. He crashes the school bus, loses his driving license, and gets fired from his job. But, while Otto is staying with the Simpsons and trying to figure out his future, Principal Skinner takes over as the bus driver. However, his driving takes forever because he’s nowhere near as willing to take risks as Otto.
As Skinner gets increasingly frustrated with his new job, it becomes apparent that, despite Otto’s slacker attitude, being a bus driver is no easy feat. Otto, though reckless, does have the required skillset (and Skinner clearly doesn’t).
Any Given Sundance (Season 19, Episode 18)
Principal Skinner and Superintendent Chalmers’ ambitions to make it as indie filmmakers are explored in season 19’s “Any Given Sundance,” as Lisa produces a documentary about her family that paints them in a negative light and gets invited to the titular festival for the premiere.
Together, Skinner and Chalmers found the production company Chalmskinn Productions and head to Sundance to sell their next movie, Ghost Willie. The show usually gets comedic mileage out of Chalmers hating Skinner, but it can be great when they get along and share a common goal, too.
The Boy Who Knew Too Much (Season 5, Episode 20)
Principal Skinner mercilessly hunts Bart down like a Terminator – or a “non-giving-up school guy” – when he skips class in the season 5 episode “The Boy Who Knew Too Much.” Bart manages to escape from Skinner’s wrath by hiding in the back of Mayor Quimby’s nephew’s car. However, Skinner is determined to prove he skipped school. Skinner’s relentless pursuit of Bart early in the episode is filled with hysterical sight gags.
When Bart is the only witness who can save Freddy Quimby from a false murder accusation, he wants to help out, but he also doesn’t want to give Skinner proof that he skipped school. It was quite an intriguing episode.
22 Short Films About Springfield (Season 7, Episode 21)
Technically, season 7’s “22 Short Films About Springfield” isn’t just an episode about Principal Skinner – it’s an anthology-style episode revolving around everybody in Springfield – but Skinner’s segment is one of the funniest. He invites Superintendent Chalmers over for a lunch of “steamed clams.” Then, when he burns the clams, he goes to Krusty Burger and claims that he calls hamburgers “steamed hams,” despite the obvious grill marks.
“Steamed hams” has since become one of the most beloved memes that originated on The Simpsons. There are 20 other segments in this episode, but the Skinner-centric one is easily the most memorable.
Bart’s Comet (Season 6, Episode 14)
When Bart tampers with the school’s weather balloon to look like a mooning Principal Skinner, his punishment is to accompany Skinner to his astrological surveys at the crack of dawn. While Skinner is chasing down the balloon, Bart looks through his telescope and spots a comet hurtling toward Springfield. He calls the observatory and gets it named after himself – but the townspeople soon realize they’re doomed.
The second half of the episode is all about the town coming to terms with its seemingly inevitable fate, but the first half gives Skinner the unfortunate double whammy of failing to put an end to Bart’s elaborate prank and having Bart swipe his lifelong dream right out from under him at the same time.
Skinner’s Sense Of Snow (Season 12, Episode 8)
In season 12’s “Skinner’s Sense of Snow,” while all the other schools are closed to accommodate Springfield’s heavy snowfall, Principal Skinner keeps Springfield Elementary open – much to the chagrin of the students.
When they’re snowed in, the kids revolt against Skinner, tying him to a chair so they’re free to forge a path of destruction through the school’s hallways. Skinner usually has the upper hand in his interactions with students, so it was hilarious to see the dynamic shift in the kids’ favor.
Bart The Murderer (Season 3, Episode 4)
Bart gets a part-time job working for Fat Tony’s crime syndicate in season 3’s “Bart the Murderer.” Complete with spoofs of scenes from Goodfellas and The Godfather, this episode is a hysterical lampoon of the mob movie genre.
It becomes a Skinner-centric storyline when Principal Skinner mysteriously disappears after being intimidated by Fat Tony and his goons. Naturally, Bart is the number one suspect. Skinner is usually contrasted with El Barto, so it was hilarious to see him in conflict with a much more dangerous foe: the mob.
Grade School Confidential (Season 8, Episode 19)
Principal Skinner and Mrs. Krabappel’s on-and-off romance began in the season 8 episode “Grade School Confidential” after hitting it off at Martin’s birthday party. Bart catches them in the act and they assign his permanent record to Milhouse to keep his mouth shut.
Skinner and Krabappel use Bart to pass love notes to one another and go on dates disguised as field trips. When he’s had enough, Bart exposes them and they lock themselves in the school as the townspeople protest outside. Skinner and Krabappel’s romantic storyline has been a mixed bag over the years, but it got off to a great start in the emotionally charged “Grade School Confidential.”
Sweet Seymour Skinner’s Baadasssss Song (Season 5, Episode 19)
Superintendent Chalmers fires Principal Skinner and replaces him with Ned Flanders after Bart lets his dog run amok in the school in season 5’s “Sweet Seymour Skinner’s Baadasssss Song.” Bart feels bad about getting his old nemesis fired and eventually befriends Skinner outside school. After years of rivalry between Bart and Skinner, it was a fun change of pace – and surprisingly emotional – to see them getting along for once.
When Flanders runs the school into the ground, Bart helps the author of Billy and the Cloneasaurus get his job back. Upon hearing that Bart is planning to get Flanders fired, Homer insists on helping.