Bart (Nancy Cartwright) is widely known as the ultimate prankster of Springfield. Without this ne’er-do-well’s ability to tap into the spirit of youth, Bartmania (and, by extension, The Simpsons‘ explosion in popularity) in the early ’90s probably would not have been nearly as significant. Bart was the poster boy of the family for a while (hence the Butterfinger commercials), and it was his unstoppable drive to keep getting into trouble that defined his appeal more than anything else. He spearheaded so many pranks, big and small, that he goes down as one of the most troublesome personalities in Springfield.
The boy has replaced his teacher’s birth control pills with Tic-Tacs, nearly killed his mother with a log when she briefly became his teacher, used Homer’s (Dan Castellaneta) credit card without him knowing, and so many more pranks that it’s futile to even try and count them all out. For that reason, it’s a challenge to decide what his greatest acts of mischief have been. There are so many different kinds that were done for so many different reasons and for so many different characters. Almost none of them are nice or done for selfless reasons, so singling out the noblest ones doesn’t work; and a prank’s level of evil doesn’t necessarily make it memorable or funny, either. Ranked below based on how funny they are, how successful they are (how well they work and if Bart gets caught), the complexity of their execution, their scale, and how much they affect the plot of their respective episodes, Bart’s greatest pranks demonstrate why Bart was (and still is) such a big deal.
10
The Cherry Bomb
Season 1, Episode 11 “The Crepes of Wrath”
In Season 1’s “The Crepes of Wrath,” Bart feels like messing with the bathrooms. Or, put it another way, making a ridiculous mess in the bathrooms. Don’t worry; it’s not that kind of mess—at least not for the most part. He tosses a lit cherry bomb into one of the toilets in the boy’s bathroom, which makes every single toilet erupt like volcanoes. Most (if not all) of the toilets in the boy’s bathroom seem empty (thank goodness), which means that water is all that emerges.
Unfortunately, there is at least one victim here. The cherry bomb didn’t just affect the boys’ bathroom; it made the girls’ toilets explode as well. This would be bad enough if any poor soul were sitting on them, but it’s much bigger of a crime when we see that Principal Skinner’s mother (Tress MacNeille) endures the power of the bomb. Skinner (Harry Shearer) gets so mad that he sends Bart to France, which launches the episode’s main plot. Skinner’s mother was actually friendly in this episode too, which raises the question: Did Bart’s prank sour her mood for the rest of the series? Either way, it’s legendary.
9
The Principal Skinner Balloon
Season 6, Episode 14 “Bart’s Comet”
Season 6’s “Bart’s Comet” begins with an epic prank. Principal Skinner planned for a weather balloon to launch into the sky in front of a large crowd, and that did happen. The problem is that Bart made a few modifications to it: the balloon looks like the principal with his pants down, holding a large sign that reads, “Hi! I’m Big Butt Skinner.” And when the prank is unveiled for all to see, it’s too late to stop it.
This is quite humiliating for Skinner, who runs after it as if he’ll be able to jump high enough to catch it. Even better, he tells the kids to throw rocks at it yet just winds up with a heavily damaged car. The man even has Willy shoot a gun at it, which leads to an explosive misunderstanding between two fighter planes. Along with Skinner racing after it later in the episode while Bart discovers a comet, this balloon causes a hilarious domino effect on Skinner that is truly one for the books. It’s still sailing the skies, too.
8
The Megaphones
Season 8, Episode 25 “The Secret War of Lisa Simpson”
A wall of megaphones plus Bart Simpson equals hearing loss. In “The Secret War of Lisa Simpson,” he puts one behind the other until there’s a bunch of them right in front of each other, the final one pointing out a window. We get a taste of how loud it’s going to be as the conga line of megaphones trembles when a mere fly buzzes past them. Bart himself is blown back from the energy, but everyone else has to face the sonic boom that travels outward.
It seems to reach every corner of Springfield. Windows break, a freed octopus attacks Dr. Frink (Hank Azaria). Even Homer’s beer bottles are shattered by the blast. There is also a ringing noise that lingers for a while afterward, which is pretty obnoxious. Bart gets into so much trouble that he’s sent to a military school as a result, making this a hilarious and ambitious prank that launches the premise for one of Lisa’s (Yeardley Smith) best episodes in the series.
7
The Octopus on the Roof
Season 8, Episode 19 “Grade School Confidential”
In Season 8’s “Grade School Confidential,” Bart is on the roof of his school with Principal Skinner and Mrs. Krabappel (Marcia Wallace). The adults’ secret romance has been found out, and it seems that they’ve lost their jobs. But now’s not the time to quit; they want to stage a protest. The principal isn’t great at causing a scene, so Bart uses an emergency phone on the roof to call none other than Kent Brockman (Shearer) of Springfield News.
Cut to Mr. Brockman in the newsroom, who tells everyone there’s an escaped octopus on the roof of Springfield Elementary. This lie is so random and ridiculous that it’s terrific in and of itself. We quickly cut to the school, where there’s clearly no octopus. Mr. Brockman is live, at which point he begins his story in his typical professional voice: “So, once again, I’ve been had.” Aside from the stellar delivery, this is also probably Bart’s most benevolent prank. This wholesome (yet no less chaotic) display of helping love win out makes sure this is one of Bart’s best episodes.
Season 3, Episode 13 “Radio Bart”
When Bart gets a toy radio for his birthday, he uses it to mess with the entire town. He throws the sound box down a well, leaves the microphone in his room, and convinces the entire town that a child named Timmy O’Toole is trapped at the bottom of this well. The first person who falls for the trick is Groundskeeper Willie (Castellaneta), but soon everyone in Springfield is up in arms to save this boy who’s so far down the dark well that they can’t even see him.
This prank is much more cruel and insensitive than funny, but everyone’s responses to it are quite funny. Soon Timmy becomes such a sensation that Krusty (Castellaneta) even has his buddy Sting record a performative song with him in the boy’s honor, making for one of the best musical guest appearances on the show. Bart does get caught, but the repercussions are so bad that he repents. This prank sketches out a great character arc for a great episode.
5
The Prank Phone Calls to Moe’s
Throughout the Series
Of course, no call or fake name can top the series of phony phone calls that Bart makes to Moe’s Tavern. Moe (Azaria) is extremely susceptible to Bart’s clever inventions, and it’s funny every time. Bart has asked the bartender for an “I.P. Freely,” an “Al Coholic,” a “B.O. Problem,” and a few names that are so outlandish that the joke is simply that Moe should really be able to figure out they’re fake.
While these phone calls are almost never anywhere near significant to the plot, there is at least one notable exception. In Season 4’s “New Kid on the Block,” Bart calls Moe’s using Jimbo Jones’ name to get some revenge. There are other interesting contexts as well, such as when Moe is supposed to be the substitute teacher but calls out names for attendance that make the students crack up. This versatile back-and-forth shows up so frequently in the show that it’s widely known as one of The Simpsons‘ all-time greatest running gags, and he never seems to get found out.
4
Bart Shakes the Beer
Season 4, Episode 18 “So It’s Come to This: A Simpsons Clip Show”
The Simpsons‘ first clip show is surprisingly solid. A major reason for that is because it’s in Season 4, at which point they pretty much only had good moments to show. The other reason would be the story that ties all the clips together: After Homer pulls a prank on Bart for April Fools’ Day, the boy tries to come up with a way to prank him back. He takes one of Homer’s beers to Springfield Hardware and puts it on some kind of automatic shake-machine.
The prank gets even funnier when Bart raises the temperature in the house to make his father thirsty enough to get off the couch. Of course, the best part is when Homer opens the beer. Bart can’t even finish saying “April Fools,” as the explosion knocks him off his feet. It also blows the roof off the house, smashes the windows, and causes a mushroom cloud the police can see a mile away. Homer winds up in the hospital, at which point the clip show begins. This hilarious inciting incident is pure Bart.
3
Bart Gives Grampa Credit for Writing the Script
Season 4, Episode 19 “The Front”
Season 4 has lots of winners, and “The Front” is definitely among them. Bart and Lisa write an Itchy and Scratchy cartoon for the animators to consider, and it’s worthy of airtime. When it gets rejected, they assume it was because they’re just kids. So they pretend it was written by Grampa (Castellaneta) instead. Sure enough, it’s accepted. Technically, this is more of a scheme than a prank, but it involves fooling a whole bunch of people, it’s very funny, and it drives the main plot.
The complexity of this trickery is another factor to consider. The kids need Abraham Simpson to go along with all this, despite the fact that he doesn’t even know what this cartoon is. They also need him to be convincing enough to the people in the Itchy and Scratchy company to not get suspicious when they meet him. Miraculously, all of this works—at least until Grampa receives an award for the script. The ceremony shows him the cartoon for the first time, and his response makes this an Itchy and Scratchy episode for the ages.
2
The National Grammar Rodeo
Season 7, Episode 20 “Bart on the Road”
Ah yes, who doesn’t know about the National Grammar Rodeo? It’s held at the Sheridan Hotel in Canada, which makes no sense at all and sounds fishy to Lisa immediately. Bart, Milhouse (Pamela Hayden), Martin (Russi Taylor), and Nelson (Taylor) scheme to go on a road trip, and this is their brilliant alibi. It’s astounding that Bart of all people would be part of any event that has to do with grammar. It’s also very amusing how the boy’s fake Latin is what makes his sister realize it’s definitely fake.
But there’s got to be some road in Season 7’s “Bart on the Road,” so all the adults fall for it. What follows is an impressively entertaining odyssey as Bart drives his three buddies down the road during Spring Break. Not to give too much away, but so many things go wrong that he has to take on a flight-attendant job and fess up to his sister. It’s still impressive that Marge (Julie Kavner) never finds out, though, which makes the ending truly one for the books.
1
Woodrow’s Letters to Mrs. Krabappel
Season 3, Episode 16 “Bart the Lover”
Bart’s most successful prank is probably also his cruelest. Learning that Mrs. Krabappel put out an ad in the paper for a man, Bart pretends to be the perfect prospect: Woodrow, a guy who writes romantic letters and has a very deep, sexy voice in Mrs. Krabappel’s mind. He wins Edna’s heart with these letters alone. When they finally set up a date in person, Bart obviously can’t go; so he has Woodrow stand her up.
When he sees that Mrs. Krabappel is heartbroken, he actually feels “partly responsible.” The guilt is so bad that he seeks help from the rest of his family. Knowing that Edna can absolutely never know she was duped by her own student, they write a break-up letter that ends things without the teacher feeling unloved or tricked. In short, this prank is a sad yet hilarious emotional rollercoaster that teaches Bart a lesson he doesn’t need anyone else to explain for once. Furthermore, he needs to drag every Simpson in the household (except Maggie) into his deceit to make sure it ends without disaster. The complexity and nuance here makes “Bart the Lover” one of the greatest episodes of all time.
The Simpsons
- Release Date
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December 17, 1989
- Network
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FOX
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Homer Simpson / Abe Simpson / Barney Gumble / Krusty (voice)
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Julie Kavner
Marge Simpson / Patty Bouvier / Selma Bouvier (voice)
