Top 10 Principal Skinner Pranks on the Simpsons
#10: A Pool Full of Earthworms
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“Pranks and Greens” Long before Bart Simpson became Springfield Elementary’s resident prankster, a student named Andy Hamilton terrorized a younger Principal Skinner. This scene works on two levels. As a gross-out gag, Skinner diving into a pool full of worms is hard to beat. But it’s the fresh glimpse into Skinner’s backstory that makes this prank so good. The scene shows how a practical joke turned Skinner from a young, laid-back educator into the neurotic tightwad we know today. Seymour Skinner never recovered from the incident, and cartoon comedy is all the better for it.
#9: Cherry Bomb
“The Crepes of Wrath” Principal Skinner is among the most notorious momma’s boys in TV history. This makes it all the more hilarious when Bart flushes a cherry bomb while Skinner’s mom is on the the toilet. Skinner is so panicked for his mother’s sake that you almost have to feel bad for the guy. Fans of the series know he’ll be getting an earful about it from mom when they get home. In one of the funniest scenes from season one, this practical joke helped establish a now-30-year-old relationship between Principal Skinner and his most mischievous student.
#8: Caught Making Out with Mrs. Krabappel
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“Grade School Confidential” This one has got to be the most cringe moment in any Skinner prank. Intent on exposing their secret romance, Bart gathers a crowd to reveal Principal Skinner and Mrs. Krabappel making out in the broom closet. This prank is more embarrassing for everyone involved than it is laugh-out-loud funny. It’s every kid’s worst nightmare to see their teacher and principal playing tonsil hockey. For a prude like Skinner, this must have been a whole new level of humiliation. It’s a rare scene in which Principal Skinner is brunt of the joke for breaking the rules rather than enforcing them.
#7: Water Balloons
“Fears of a Clown” This makes our list for being one of the most satisfying revenge-gags in the “Simpsons” canon. Bart is determined to have the last laugh after Skinner lands him in prankster’s rehab. In a characteristic bait-and-switch, Bart lures Skinner (and plenty of other Springfield onlookers) with a phony apology only to unleash an armageddon of water balloons. The whole episode leads up to this moment, and it really pays off when Bart finally gets his revenge on Principal Skinner. It might not be the funniest prank ever pulled on him, but it’s definitely one of the most cathartic.
#6: Threatened with Peanuts
"Please Homer, Don’t Hammer ‘Em" This might be the most dangerous prank ever pulled on poor old Seymour Skinner. After learning about his deadly allergy, Bart uses peanuts as a weapon to force Skinner into all sorts of embarrassing and downright painful situations. It’s a pretty sadistic practical joke, but the montage shots and upbeat music keep the tone light and on-brand for “The Simpsons.” Fun fact: The Ramones, a seminal New York punk band who lent their song “Beat on the Brat” to this scene, were huge Simpsons fans. They made an infamous cameo to sing “happy birthday” to Mr. Burns in the show’s fifth season.
#5: A Giant Tomato
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“Duffless” In a simple but sweet slapstick gag, Bart just can’t help himself when Lisa hands him her giant, hormone-infused tomato. It’s the comedic sense of anticipation that makes this scene work. From its vantage point atop the school steps, the camera shows an ever prim and proper Principal Skinner bending down to tie his shoes. We see this moment through Bart’s eyes when Skinner wiggles his exaggeratedly large behind and slowly, methodically ties his shoes. We’re practically begging for it by the time Bart throws the tomato. The slow-mo impact shot makes this one of the most visually-satisfying pranks in “Simpsons” history.
#4: Trampled
“Team Homer” This one’s another practical joke that makes great use of comedic anticipation. We see Skinner beaming with delight as Superintendent Chalmers praises him for a flawless yearly review. Unbeknownst to them, Bart Simpson has just unleashed anarchy among the students of Springfield Elementary with his ‘Down With Homework’ T-shirt. They trample Chalmers just as he’s about to finish writing Skinner a perfect review. It’s a masterful example of situational irony: a discrepancy between what the audience and the characters know. To top it all off, seeing Skinner and Chalmers trampled by a bunch of children makes for fantastic physical comedy.
#3: White Suit Ruined
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“Little Girl in the Big Ten” Practical jokes are all about the timing, and this scene is no exception; what better moment to humiliate Skinner than when he's full of pride? Skinner is practically begging to be pranked when he stands right next to a giant cake while wearing a white suit. In a stunt to win back her popularity, a bubble-protected Lisa dives from the roof and covers Skinner in chocolate. Not only is this a delicious payoff, it's an interesting moment in Lisa's arc as a character. Even Springfield Elementary's best student is capable of pulling one over on Principal Skinner.
#2: Magnetic Shoes
“The Debarted” It’s the perfect setting of this prank that lands it so high up on this list. What better place to humiliate a proud principal than his own auditorium? Just as Skinner is about to take the stage for a routinely-boring school assembly, Bart uses magnets under the stage to force him to dance. It might not have the cerebral qualities of other “Simpsons” jokes, but Principal Skinner breakdancing to an auditorium of cackling children more than makes up for it. Bart’s stage dive makes for a perfect ending.
#1: Big Butt Weather Balloon
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“Bart’s Comet” Bart takes his pranking to cosmic proportions in season six when he turns a weather balloon into a caricature of Principal Skinner. In one of the most iconic jokes in Simpsons history, the inflatable principal moons onlookers while holding a sign that reads “I’m Big Butt Skinner.” The transition from pride to humiliation in Skinner’s demeanor just seals the deal. It’s a punchy joke that encapsulates the best elements of a Skinner prank: embarrassment and juvenile humor, all at the expense of Springfield’s most high-strung administrator.
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