The Best Bart Simpson Moments On The Simpsons

Despite a large universe of Springfieldians from which to draw, most installments of The Simpsons tend to be "Homer episodes" or "Bart episodes." It's no secret as to why: Those two characters are uniquely strong, developed, and memorable. When the series made its sensational launch in 1989, Bart Simpson received a  particularly huge degree of attention — TV had rarely championed a character so unabashedly proud of his misbehavior. The years since have not dimmed the character's appeal. If anything, they've only drawn it into sharper focus.

Bart Simpson is the very definition of a punk kid, devoted to being an irksome menace to his principal, teacher, parents, sister, and his long-suffering best friend, Milhouse. Over time, Bart has become a very realistic character, his mischief shaded in with real emotion. Bart is a lens through which Simpsons writers examine (and mock) every aspect of American life, particularly what it's like to be a kid in the midst of it. As a result, Bart has enjoyed a lot of wild adventures and learned many life lessons over the years. These are the most memorable and entertaining of those moments.

One of Bart Simpson's greatest moments is also one of Principal Seymour Skinner's worst. In 1995's "Bart's Comet," Skinner launches a weather balloon as an educational treat for his students at Springfield Elementary. But when it's unfurled, he's embarrassed to see that someone — Bart, obviously — has altered it. It bears the principal's likeness, his rear end exposed, holding a sign that reads, "Hi, I'm big butt Skinner." Skinner discovers Bart's balloon-changing blueprints and, as a creative punishment, sentences the boy to assisting him on his 4 AM astronomy projects. During an ensuing stargazing session, Skinner takes a brief break from reciting coordinates to a bored Bart. Bart wildly spins around the principal's carefully calibrated telescope, and winds up discovering a comet, a goal Skinner has passionately pursued. Bart is always good at bugging Skinner, but he irritates the man on a deep psychological level here. Bart steals Skinner's lifelong ambition out from under him, just by being his reckless self. That act, combined with the petty, puerile, and very funny balloon prank from before, makes this an all-time great Bart-centric episode.

For a show that brutally satirizes most aspects of modern life, The Simpsons is surprisingly restrained when it comes to matters of faith. Consider the 1995 episode "Bart Sells His Soul." At the beginning of the episode, Bart pranks his entire church by passing out sheet music for what seems to be a hymn, but is actually Iron Butterfly's psychedelic rock masterpiece, "In-A-Gadda-Da-Vida." Punished by Reverend Lovejoy (along with Milhouse, for snitching), Bart calls the entirety of organized religion and the idea of spirituality itself into question, proving his lack of belief by selling his soul, symbolized by a piece of church stationery with "Bart Simpson's soul" written on it, to his friend for five bucks. All goes well, until the act begins to haunt Bart — Marge thinks there's something off about him, and he has a memorably disturbing dream in which all of his friends sail to heaven while he's left to languish, alone and soulless. Bart ends up riding his bike across town to find Milhouse and get his soul back. He can't — Milhouse sold it for Alf Pogs. Bart does finally get his soul back, but his long, dark night of the scribbled-down soul isn't easily forgotten.

Bart Simpson does a lot of bad stuff, but he's not evil. His stunts aren't usually premeditated — he merely sees an opportunity for fun and goes for it without considering the consequences. The 1996 Simpsons episode "Bart on the Road" begins with one such last-minute act. When Principal Skinner realizes his vacation flight to Hong Kong leaves on the last day of school before spring break, he cancels classes and declares it "Take Your Kids to Work Day." While Lisa gets to go with Homer to the nuclear power plant, Bart gets sent off to the DMV with his aunts Patty and Selma.

It's a famously boring place, but the easily entertained Bart makes his own fun. With his aunts occupied, Bart gets hold of the driver's license-making machine and makes one for himself. Technically, it's a fake ID ... but also technically it's a real, government-issued ID with his real 10-year-old face on it, albeit accompanied by a fake birth date. And so Bart embarks on a road trip, picking up Milhouse, Nelson, and Martin for a journey to Knoxville, Tennessee. Bart explains his absence with the dumbest, most unbelievable excuse possible: He claims he's going to the National Grammar Rodeo in Canada. All in all, it's one of Bart's greatest schemes, even if Knoxville turns out to be less fun than he'd hoped.

Bart Simpson is a legendary agent of chaos. But he's also still a kid, and often finds himself acting according to the whims of his parents. In 1997, The Simpsons used Bart as a vehicle through which Homer Simpson reckons with his attitudes toward gay people in the episode "Homer's Phobia." The family enjoys a kitschy memorabilia store in the Springfield Mall and makes fast friends with proprietor John, played by the one and only John Waters. Homer loves John ... up until he realizes that John is gay.

Soon after his discovery, Homer falls into a spiral of paranoia, becoming convinced that Bart might be gay as well. His rationale? Well, Bart puts on a wig and dances to Cher while wearing a Hawaiian shirt (Bart says it "came out of the closet") and emphatically shouts "zap!" while playing with a toy laser gun. Bart then endures Homer's attempts to shore up his heterosexuality, which consist of sitting him down in front of a cigarette billboard and taking him to a steel mill. Unfortunately, that steel mill is staffed by gay men, who turn it into a nightclub during breaks. Bart only realizes why his dad is putting him through all of this at the very last second of the episode. He might not be directing the action of this episode, but he's a great catalyst for it.

The Simpsons is probably the only show on TV that can start an episode — 1993's "Boy-Scoutz 'n the Hood" – with a show-stopping musical number, then end on a fast food outpost on an offshore oil rig. After finding 20 bucks on the ground, Bart and Milhouse hit up the Kwik-E-Mart for a Squishee made entirely of syrup. This concoction is so sugary that it basically gets them drunk, inducing a "Broadway style" sequence in which the duo have a crazy night on the town.

When Bart wakes up the next morning with a wicked Squishee hangover, he's shocked to discover that in his inebriated state, he enlisted ... in the Junior Campers scouting organization. He desperately tries to worm his way out of his commitment, until he realizes the gig allows him to play with knives. However, he nearly dies on a father-son canoeing trip when Homer's bad decisions leave them (and the Flanders family) adrift at sea. Their lives are saved when they stumble upon a very remote Krusty Burger. It's a hallucinatory whirlwind of an episode, and all the better for it.

It seems like at one point or another, every long-running sitcom attempts the episode-length parody of Alfred Hitchcock's Rear Window. The Simpsons' 1994 send-up, "Bart of Darkness," is among the best of its ilk, succeeding by placing Bart entirely out of his element. Early in the episode, the Simpsons get a pool, and, of course, Bart breaks his leg almost immediately. He is forced to watch his friends have fun all summer long from the confinement of his bedroom. At first, he hilariously tries to pass the time by writing a stage play that reads like a century-old British farce. Then he gets a telescope ... and thinks he sees Ned Flanders murder Maude, then cover it up. Bart slowly goes mad, his paranoia building with every second he remains trapped indoors. As it turns out, however, Ned only murdered Maude's favorite plant while she was away. Those girlish, high-pitched screams? Ned himself. Case closed.

By 1994, when "Bart Gets Famous" first aired, The Simpsons had reached near-universal popularity. You couldn't walk into a high school in the US without seeing at least a couple of Simpsons t-shirts. Many of them bore the image of Bart Simpson uttering one of his mischievous catchphrases, like "Eat my shorts," "Underachiever and proud," or "I didn't do it, nobody saw me do it, you can't prove anything." Art imitates life in "Bart Gets Famous," as one of Bart's quips, "I didn't do it," becomes a pop culture sensation.

Bart's in-world fame allows the show to make fun of itself and the arbitrary, fleeting, and ultimately hollow nature of the zeitgeist. It all begins when Bart sneaks away from a boring class trip to a box factory (leaving behind his red hat, making Homer think his boy has been transformed into a box) and heads to the Channel 6 studio, where Krusty hires him as his personal assistant. One day, he gets to say a line in a sketch, but he accidentally destroys the set and claims he "didn't do it." Thus he's launched into the unsatisfying world of fame, which includes a spot on Late Night with Conan O'Brien, where the former Simpsons writer-turned-host voices himself.

In the 1992 Simpsons episode "Bart the Lover", viewers see that while Bart loves to play a prank, even he has his limits. Shortly after receiving a month of after school detention, Bart discovers a personal ad written by his teacher, Ms. Krabappel. He decides to toy with the lonely woman's emotions, answering the ad as a guy named Woodrow (pulled off of a classroom presidential portrait) and sending her a picture of hockey great Gordie Howe cut out of a book. A correspondence develops, and Bart ends up composing love letters by piecing together lines from old movies and Homer's notes to Marge. "Woodrow" proposes a meet-up at The Gilded Truffle. But when Bart looks in the window at the appointed time and sees Krabappel stood up and alone, it breaks his heart. He lets her down gently with one final letter. Bart is a real softy ... when he wants to be.

Rarely does Bart Simpson get away scot-free with a prank or scheme, but in the 1992 Simpsons episode "Radio Bart," the ramifications for what he does are particularly swift and intense. His birthday present from Homer is a Superstar Celebrity Microphone, a toy that amplifies a voice over radio waves. Bart doesn't care much for it, until he realizes he can use it to mess with people. He speaks as the voice of God over Rod and Todd Flanders' radio, and broadcasts over a radio he lowers into a well, pretending to be Timmy O'Toole, an unfortunate little boy who fell in.

This episode aired just a few years after baby Jessica McClure's rescue from a backyard well became a media sensation. The town of Springfield rallies similarly around poor Timmy. When he realizes he's gone too far, Bart climbs into the well to get the radio out, but gets trapped when his foot is caught under a rock — the same fate he'd made up for Timmy. Bart calls for help and explains that there is no Timmy. The town is so miffed that they leave him there. Bart feels pretty bad about what he did, but fortunately, he's rescued by celebrity guest star Sting, who's a very good digger.

For both a 10-year-old and a fictional character, Bart Simpsons has a tremendously well-developed sense of self. He knows who he is, and he's comfortable with it. His position as the town's biggest menace (and thus his sense of self) is threatened, however, in the 1994 Simpsons episode "Bart's Girlfriend." For one thing, he allows himself to be vulnerable enough to develop an intense crush on a girl. For another, she turns out to be far more callously evil and destructive than Bart himself.

At  first, Bart's infatuation with Jessica Lovejoy makes him try to change his wicked ways. She's the daughter of Reverend Lovejoy, and presumably a good and upright young lady. But she only reciprocates his interest after he tells an off-color story in front of her parents. The two set off on a whirlwind romance of vandalism and petty theft. It's a rare treat to see the usually confident and independent Bart so conflicted and under someone else's thumb ... until things get out of hand, of course.

The 2020 episode "Bart the Bad Guy" finds young manipulator Bart Simpson benefiting from the worldwide obsession with avoiding "spoilers" for highly-anticipated films. After sending Milhouse to the hospital by making him imitate a dangerous stunt from a viral video, Bart pretends to be Milhouse when superhero movie actor Glen Tangier comes to visit. The star arrives with a laptop bearing a cut of the Avengers-esque Vindicators: Crystal War 2: Resurgence. After Tangier drinks himself to sleep (to cope with having to visit so many sick and dying children), Bart watches the movie and declares himself Spoiler Boy. He convinces Comic Book Guy to give him most of his store so he won't reveal spoilers, talks Principal Skinner into handing over his toupee, and holds most of the town hostage by threatening to blurt out spoilers should anyone cross him. It's a brutal look at the modern mania over spoilers, and, depending on your stance, possibly one of Bart's worst acts.