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10 best Bart Simpson-Principal Skinner rivalry moments

10 best moments in the Bart Simpson-Principal Skinner rivalry
Principal Skinner has had his share of victories, as well as failures and moments of peace with Bart Simpson. Their relationship would not be a great feud otherwise. (Photo by FOX via Getty Images)

Starting at the end of next month, Bart Simpson will round out his third decade in fourth grade.

For viewers who have kept The Simpsons running this long, this partially means anticipating new Bart-versus-Skinner storylines. Past its peak or not, the show will surely keep revisiting that dynamic.

During its golden years, relying on the classic kid-antagonizes-authority-figure motif was a sensible decision. With the advantage of being a TV saga, Bart and Skinner have superseded the legacy of any student-principal spars from John Hughes movies.

And you can see where Bart’s mischievous streak, let alone his propensity to dispense it in school comes from. In “Homer Goes to College,” Bart’s father holds an adamant grudge against Springfield University’s easygoing dean. Homer was also a ring-leading thorn for his high-school principal, as “The Way We Was” established.

In its stagnating present, The Simpsons has served up a balanced bounty of victories for Bart and Skinner alike. There have even been some memorable moments of peace, such as the better part of “Sweet Seymour Skinner’s Baadassss Song.” A rivalry cannot be top-notch without each of those.

Among the times when the feud is hot, though, these are the top 10 plots and scenes in Simpson-Skinner history.

10. “The DeBarted”
The Simpsons as a whole has looked like a subpar reboot of itself throughout this century. With that said, it can still produce humorous slivers worth archiving on YouTube.

To wit: Bart makes Skinner’s loafers magnetic and sneaks under the auditorium stage prior to an assembly. When he gets to work, a full minute of juvenile hilarity ensues.

Skinner will reemerge and add his own humor to the sequence by whipping out his guide to Catholic school punishment. But not before falling into a disposal of retainers, a la the “clumsy Clouseau-esque waiter” who plummets into a truck of rat traps. (More on that episode later.)

9. “Whacking Day”
Whether it is superior cunning, daring or both, only Bart busts out of Skinner’s confinement for the school’s topmost troublemakers. As the visiting Superintendent Chalmers soon reveals, the timing could not be worse for Skinner’s career.

When Bart strikes Chalmers with a tractor, the superintendent tells Skinner that a potential promotion is off the table. In turn, Skinner expels Bart, who turns and watches the tractor have the last laugh.

8. “Bart After Dark”
In an unexpected, unintended table-turn, Bart lands Skinner in a little hot water. The principal is somehow oblivious to the kid’s presence at the burlesque house as he details his apparent interest in one of the dancers.

Skinner pathetically tries to backtrack once reality hits. He then reports Bart to the Flanders and Lovejoys, who in turn visit Homer. Had he kept mum, neither he nor anyone else would have been exposed in the subsequent town-hall slideshow.

7. “Homer vs. Patty and Selma”
This is not the last time a pop-culture protagonist skips school when it would have been better if they went. The title character on Hey Arnold! and his friend Gerald missing a surprise daylong carnival comes to mind.

But nothing tops the instant karma Bart brooks for missing too much of athletic sign-ups. Skinner swiftly rubs the consequences in his foe’s face by dramatically revealing ballet as the only option with open spots.

6. “Brother’s Little Helper
This episode premiered in the fall of 1999, when the show was convincingly (but barely) clinging to its overall entertainment value. Fittingly, this is when Skinner displays his most visible ire with Bart’s antics.

Throughout the school’s outdoor fire-safety assembly, Bart tests Skinner’s patience. His onslaught of childish jokes and daring stunts essentially represent all he has dished out through the program’s decade-long canon.

Everything culminates in a destructive firehose-in-the-gum surfing prank, which Lisa and Bart both admit tops his previous troublemaking. Afterwards, Skinner vents by punching an inflatable clown in front of Bart’s parents.

5. “Lisa’s Sax”
Two years before Skinner’s hot blood reaches a fever pitch, we look back on the birth of this rivalry. Near the dusk of the show’s quality, this flashback-heavy episode details the origin of Bart’s class-clown persona.

For a moment, the drama holds up when Bart gulps at Skinner’s stern response to his insubordinate taunting. Naturally, though, the kid decides the majority overrules the principal’s towering presence.

Skinner proves right after humorously mispronounces his name to the new kindergartners and lamenting, “I’ve lost them forever.”

4-3. “The Boy Who Knew Too Much”
“You’re mine, Simpson,” evokes memories of Edward Rooney in Ferris Bueller’s Day Off. Moments later, Skinner’s determined descent into the river reminds many, including showrunner David Mirkin, of Westworld.

Everyone knows that Skinner knows Bart is truant. The catch is, well, he cannot catch him, thus cannot produce concrete proof.

The ensuing suspense survives through the trial of Freddie Quimby. As such, this episode yields a two-in-one package of Bart-Skinner moments.

The boy’s mind-reading ability is hardly a blessing when the principal-turned-juror leaves him sweating in the courtroom. For the audience, though, it yields a humorous twist when Skinner admits, “I think words I would never say.”

2. “Bart’s Girlfriend”
Stepping out of school and scouting the town would not be the greatest lengths Skinner goes to. Although at least in that case, the student had already broken a rule of his own accord. This time he falls into a trap off school property and outside school hours.

It is unclear whether Bart owed substantial time in back detention service or if Skinner had another motive. The immense resources he puts into his Scotchtoberfest sting stand out all the same. So does his smug pleasure in quickly quelling Bart’s glee and doling out the sentence.

The bigger question in this sequence is how the Scottish-American Groundskeeper Willie never knew the festival was a scam. His outrage is understandable, as both the student and principal exploited him.

1. “Bart’s Comet”
Skinner builds everything up, only to have it break down for him in this episode’s tone-setting segment.

As punishment for tastelessly putting his likeness on a balloon, the principal forces Bart to rise at 4:30 a.m. and join him in an ostensibly boring astronomy project. Amidst their shift, he darkly recalls his closest shave with success in this field.

“By the time I got to a phone, my discovery had already been reported by Principal Kahoutek. I got back at him, though. Him and that little boy of his.”

Just his luck, or his ill-advised decision, Skinner then steps away for one moment. That is when Bart disobeys his orders by looking through the telescope and noticing the title comet.

Skinner’s latest failure is compounded by the second escape of Bart’s balloon and an unflattering newspaper headline. If only Springfield Elementary had a poster with the proverb about chasing two rabbits. The principal would have had a much better early morning if he paid heed to that.

Al Daniel

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