If you’re even remotely familiar with The Simpsons, you’ll know two things about the show’s characters: Homer is one of the most absurd, over the top, hilarious dads in sitcom history, and his son Bart is a relentless troublemaker. Their combined antics are key to the show’s success.
Bart’s reign of terror over his family, his classmates and his whole town (his graffiti tag, El Barto, is plastered absolutely everywhere in Springfield) is well-known, but if he has just one favorite victim, it’s the long-suffering Principal Skinner. Over the show’s long run, Bart has pulled all kinds of pranks on Skinner, some that put the Principal’s very life in danger. Let’s take a look at some of the worst ever.
The Magnets-In-The-Shoes Prank
This was quite an elaborate one, granted, but it still lacks a little of the artistry that marks some of Bart’s very best pranks.
In the episode “The Debarted,” Bart finds he has a rival in the shape of Springfield Elementary newbie, Donny. To out-do Donny, he sneaks metal soles into Skinner’s shoes while the Principal is out of the office, later using magnets from beneath the stage to make Skinner dance involuntarily as he gives an assembly. The ending flourish (in which he’s flung outside into a pile of discarded retainers) was a nice touch, but Bart has definitely still done much better.
Lisa’s Prank
Suffering from “Panda virus” after being bitten by a mosquito that was in a toy of his, Bart is quarantined in a plastic bubble by Doctor Hibbert. His sibling is having problems too, losing (even more) popularity at school after her friends found her attending college behind their backs.
To win Lisa her friends back, Bart suggests a prank: Chalmers is dedicating the Seymour Skinner parking annex to the Principal, who will pose beside an elaborate chocolate cake in his finest suit. He pushes Lisa, who is inside the bubble, into the cake from the roof above, covering the Principal’s suit in gooey, chocolatey mess. Yes, it was technically Lisa who perpetrated this dastardly deed, but who was the mastermind behind the prank? Bart, of course. Again, Skinner was humiliated in front of the Superintendent and students, but this is still a little minor league.
“Down With Homework”
If Principal Skinner has a mortal enemy besides Bart, it’s Superintendent Chalmers. The man seems determined to condemn Springfield Elementary and fire Skinner. What happened the one time Chalmer’s was incredibly impressed with the school and was about to give Skinner’s leadership a perfect ‘10’? Well, naturally, Bart happened.
During Chalmer’s visit, Bart decided to reveal the t-shirt he was wearing, which read “Down with homework.” His classmates, inspired by this slogan, soon went on a rampage through the corridors. Of course, Chalmers and Skinner had a front row seat.
Working Together With Donny To Turn The Tables On Skinner
As we’ve seen, then, Bart felt very threatened by Donny, the capable prankster who stole a lot of his thunder. As it turned out, he had good reason to be wary of the new kid: he was an informant of Skinner’s, who was seeking a new way (along with Chalmers) to have Bart suspended.
Bart felt all kinds of betrayed, having allowed Donny into his inner circle. At the end of “The Debarted,” though, Donny has a change of heart, turning on Skinner, Chalmers and Willie and catching them in the gang’s trap (the classic coke-and-mentos). Having the tables turned on him in this moment of triumph must have pained Skinner to no end. It was an indirect deed on Bart’s part, though, so we can’t rate it any higher.
The Cherry Bomb ‘Attack’ On Agnes Skinner
As all fans of The Simpsons will know, if there’s one person Seymour Skinner dotes on, it’s his mother. For her part, Agnes Skinner doesn’t exactly show a lot of affection for her son, but the two are very close regardless.
In “The Crepes Of Wrath,” Bart goes much too far when he finds an old cherry bomb in his bedroom, takes it to the school and flushes it down the toilet. Poor Agnes (of course she was visiting the school bathroom at this exact moment), is blasted right out of the stall by the explosion. Searching for a punishment tough enough for the heinous crime, Bart is deported to France as part of the school’s exchange program. While this wasn’t Bart’s most artful prank, the severity of the punishment warrants the middle spot on this list.
The “Buttzilla” Weather Balloon
Now we’re getting to some of Bart’s more ingenious and devious pranks. The pride of Springfield Elementary’s Science Week was a weather balloon, to which Bart secretly added a modification or two prior to its launch: at the pull of a rope, the balloon unfolded to reveal a likeness of the Principal and his butt, along with a sign that read “Hi! I’m big butt Skinner.”
The Principal, aghast, asked the students to throw rocks to bring the balloon down, but many of them hit Skinner’s car instead. Needless to say, he was furious about the whole incident.
Stealing Skinner’s Thunder
That wasn’t the only terrible crime against the Principal that Bart committed in “Bart’s Comet.” For the trick, he was forced to help Skinner in his amateur astronomy. Naturally, he messes with the carefully-calculated positioning of the telescope the moment Skinner briefly leaves (to apprehend the balloon when he spotted it).
Taking a casual look through it, he notices a comet, a deed for which he immediately becomes famous. Skinner is incredibly resentful, as it had been a long-held ambition of his to discover something in the skies himself.
His Response To Skinner’s False Retirement
Now, if you’d been tormented by Bart as often and creatively as Skinner has, you wouldn’t blame the Principal for devising a range of crafty revenge schemes of his own. In “Fears Of A Clown,” he arranges his own retirement as a ruse to get Bart to try and pull a prank on him and catch him in the act.
The Principal is successful, and Bart plots his own way to get even in turn: supergluing Krusty masks on Skinner and others’ faces. This trick has ramifications beyond anything Bart anticipated, seeing his mother insist that he go to rehab for a month. At the end of his treatment, he goes on to stage a mock apology, having rigged up a huge quantity of water balloons above the crowd. This wasn’t quite Bart at his worst, though: just wait for the final two entries!
Taking Advantage Of Skinner’s Peanut Allergy
Now, there are some things that you just shouldn’t mess with. Allergies, which are potentially life-threatening, are one of them. Still, when Bart discovers that it’s Skinner who has the mysterious peanut allergy in “Please Homer, Don’t Hammer ‘Em,” he’s determined to use this fact to further torment his principal.
Threatened by Bart’s peanut on a stick, Skinner publicly embarrasses himself at Bart’s whim. It’s all played for laughs, of course, but there’s something sadistic about this. The fact that Skinner discovers Bart’s shrimp allergy and duels him with a shrimp on a stick makes things much easier to swallow, though, and this wasn’t quite the worst thing Bart ever did to his Principal.
Actually “Killing” Him
For some dedicated pranksters, it can be hard to tell where to draw the line. Here’s a good rule of thumb: if your victim actually dies, it’s safe to say that you’ve gone just a shade too far.
In “Bart The Murderer,” Bart strikes up an association with Fat Tony and his men when he happens upon their bar. They employ him when they discover he makes a fantastic Manhattan, only for him to be late to a vital ‘business engagement’ after being punished by Skinner at school. The mobsters confront the Principal, after which Skinner goes missing. It’s initially believed that he was killed by the mob (for which Bart blamed himself and had nightmares about being executed for the crime), before it’s revealed that Skinner had simply been trapped in his own home by falling newspapers. Still, this was looking super bad for a while.