Pop culture obsessives writing for the pop culture obsessed.
Pop culture obsessives writing for the pop culture obsessed.

The Simpsons (Classic): “The Boy Who Knew Too Much”

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“The Boy Who Knew Too Much” (season five, episode 20; originally aired 05/05/1994)

In last week’s entry, I wrote about “Sweet Seymour Skinner’s Baadasssss Song” as an atypically small, intimate episode of The Simpsons, especially for a landmark 101th episode. In its halcyon prime, however, The Simpsons was never afraid to go big, and the show’s 101st episode, “The Boy Who Knew Too Much” is an illustration of The Simpsons at its most epic and ambitious. It’s also an episode steeped in Americana, in the rich folklore and tradition of our country. It touches upon the boys’ own adventures of Tom Sawyer and Huckleberry Finn, the complicated cultural legacy of The Kennedy family, the legal system, and even Abraham Lincoln, who shows up in one of Bart’s daydreams about Huckleberry Finn, possibly because he’s the only historical figure Bart would know from around the same time period.

“The Boy Who Knew Too Much” has trenchant philosophical questions at its core. Should a man go free if he’s innocent of the specific crime he’s accused of but guilty of making the world a worse place and being a deplorable human being? Or does it serve the greater public good for people like that to be locked away? Should a man testify on behalf of another man in order to save him even if it means condemning himself in the process?

Considering how prominently guilt figures in the narrative, it’s only fitting that the episode begins with Otto picking up students in a prison bus. At school, Bart forges a note for a dentist’s appointment that fools Mrs. Krabappel but not Principal Skinner, leading to an intense game of cat and mouse between the student and his principal. Skiner uses his own personal preferences as a guide to where Bart might be found, flummoxed to find him neither at the 4-H Club nor at the Springfield Natural History Museum.

In his bid to escape Skinner’s prying eyes and relentless pursuit, Bart ends up slipping inside a car driven by Freddy Quimby, the asshole nephew of Mayor Joe Quimby. Mayor Quimby is famously portrayed as an amalgalm of the Kennedys minus their redeeming facets and tony charm. He embodies their arrogance, lust, greed, inexorable will to power, and incredible sense of entitlement without the charisma and personal magnetism that renders the family and its members (theoretically) bearable.

In The Simpsons universe, powerful political dynasties barely bother to hide their misdeeds. In one of the most quotable lines from the episode, Mayor Quimby offers his nephew the benediction, “May all your disgraces be private!” This coming from a character who’s never been shy about broadcasting his wanton misdeeds.


Freddy comes off like a mutant version of Mayor Quimby with five times the mindlessly destructive speed and 10 times the incoherent, meaningless rage. He’s the raging id of “Diamond Joe,” who is pretty much all raging id himself in the first place. The younger Quimby crashes his sports car into his own birthday party, hurls a football into the punch bowl, then brays that the punch has been spiked. He generally behaves as if the world exists for his own sneering, debauched amusement. When a French waiter pronounces “chowder” at the soiree in a manner Freddy finds amusing, he angrily demands that the French waiter repeat it, only to have the waiter refuse. Nobody says “no” to Freddy Quimby, so when the French waiter is found covered in bruises, Freddy is understandably the main suspect.

While lurking about the party, Bart oversees the waiter take a series of Peter Sellers-style pratfalls after his verbal altercation with Freddy that mirrors the injuries one might sustain while being throttled mercilessly by the petulant scion of a prominent political family. He’s reluctant to step forward, however, because doing so would involve outing himself as a truant.


Freddy certainly seems like the sort of person who would viciously beat someone for their pronunciation of “chowder,” a word I suspect was chosen because it never stops being funny. The evidence would seem to indict Freddy. Freddie's personality would seem to indict Freddy. There’s only one problem: Freddy’s innocent.


Sure enough, Freddy is put on trial, and the fix is in from the very beginning. Moe accepts a giant bag of money (the dollar sign on the bag is a bit of a giveaway) for providing a false alibi involving having been with Freddie doing charity work for people in one of those “loser countries” at the time he was supposed to be attacking the waiter.


Homer, meanwhile, is called for jury duty and makes an auspicious discovery: As long as the jury is deadlocked, he can continue to enjoy the free room-service indefinitely. (This is also the premise of the Pauly Shore vehicle Jury Duty, as I’m sure I do not need to remind you). Homer succeeds in delaying the trial long enough until Bart’s conscience begins to really gnaw away at him and he decides to do the right thing—even if it means freeing a bad man and dooming himself to Principal Skinner’s punishment.

The expansive plot offers the show an opportunity to comment on our complicated, love-hate relationship with people in power—political dynasties in particular. Marge echoes the thoughts of plenty of people who despise the Kennedys individually and as a group and take pleasure in their considerable misfortune when she says, “Those Quimby children are so wild and rich. I hope he finally get what’s coming to him!” In Marge’s mind, and in the public imagination to a certain extent, the wealth of the idle rich is inextricably linked to their wildness. There’s the sense that something should be done about them, that their wealth and status and power free them from having to conform to the same rules and laws and regulations that the rest of us follow. So when they’re accused of a crime, they’re generally considered guilty until proven innocent. Accordingly, pummeling that French waiter is probably the only terrible thing Freddie isn’t guilty of.


“The Boy Who Knew Too Much” is The Simpsons at its biggest and its best. It’s a rollicking exploration of guilt and shame, class and perception that tackles the big issues without sacrificing the belly laughs and smooth, swift plotting fans angrily demanded and almost invariably received back when The Simpsons could do just about no wrong.

Stray observations

  • “The bus and I have kind of a Shining thing going on”—Otto on the bad vibes that make the bus go round and round
  • I’m kind of tempted to use Bart-Bart as an alter ego.
  • I love how moderately more profane Skinner is in his thoughts.
  • I also enjoy that Skinner thinks of Free Willy as being a film about a disobedient whale.
  • Do Uncle Arthur and his unusual theories of justice ever come up again?
  • “He’s like some sort of non-giving-up School Guy”—Bart’s ineloquent tribute to Skinner’s unstoppable persistence.
  • Next up is “Lady Bouvier’s Lover.” If memory serves, that’s a good one.