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The worst things Bart Simpson has ever done

The TV landscape has changed dramatically since The Simpsons premiered in 1989. The envelope has been pushed so far, it's practically nonexistent — if you can imagine a dark jokes about a sensitive topic, chances are a post-Simpsons animated comedy like South Park or Rick and Morty has already made it.

But back in the not-so-long-ago days of The Simpsons' early years, there was just one animated bad boy, and he wore shorts, carried a slingshot in his back pocket, and terrorized his small town. Bart Simpson has perpetrated many mischievous schemes over the years, from pranking the school principal to inciting a flat-out international incident. Whether his crimes are big or small, Bart isn't afraid to dive headfirst into recklessness each chance he gets — which means there's no shortage of examples in which he's been a terror to everyone around him. 

Over the years, a handful of his pranks and antics have crossed a serious line. To help separate the fun kind of bad from the, well, bad kind of bad, we've compiled a rundown of the worst things Bart Simpson has ever done. Eat his shorts indeed.

Stirring up an angry mob

The people of Springfield will form an angry mob at the drop of a hat. "The Telltale Head" marks one of the first times fans encountered this tendency — and one of the first episodes of major trouble Bart gets himself into.

It all begins when Bart befriends a trio of bullies. During a hang-out session, they joke about cutting the head off the statue of Jebediah Springfield that sits in the town's center. Bart, eager to impress his new friends and emboldened by a speech from Homer about the importance of popularity, decides to actually do it.

Clad in his best ninja attire, Bart snatches the head — only to wake the next morning to find that the act of vandalism has had a profound impact on the town.The denizens of Springfield descend into a frenzy, demanding justice for their beloved town founder. Bart really starts to feel the pressure of what he's done when he overhears his antagonistic new friends saying they'd like to pound whoever actually went through with the decapitation.

When Bart is finally overwhelmed and confesses, it forces him and Homer (who takes partial responsibility, thanks to his pep talk) to outrun an angry, torch-bearing mob in order to return the head of the statue.

Causing an international incident with Australia

Bart's ways catch up to him on a global scale in "Bart vs. Australia." When he doesn't believe Lisa's explanation of the Coriolis effect, Bart calls up Australia to check which way their toilets flush. When he subsequently leaves the line open for several hours, a justifiably furious Australian man demands Bart pay the $900 bill.

Instead, Bart does what he does best and mocks the man before hanging up. Unfortunately for him, the man happens to be connected to a member of Parliament, who is close to the country's Prime Minister. When Bart tosses all of the collection notices he receives in the trash, the country's State Department indicts him, telling him that he'll have to come to Australia to personally apologize, revealing at the last minute that he'll also be booted on the backside as punishment.

Homer becomes enraged at the idea of Bart being booted, and the two escape custody and run back to the US embassy, where Bart further taunts the angry Australian people by mooning them. This forces the US Marine Corps to evacuate them by helicopter.

As they leave, it's revealed he also brought a bullfrog with him on the plane, which he let loose in the airport when it became clear he couldn't get it through customs. The frog multiplies and overwhelms the unprepared country, leaving plague-like devastation in the fourth-grader's wake.

Shoplifting a video game

Admittedly, this doesn't sound that bad, compared to other entries on this list. However, the emotional fallout of this crime, as depicted in "Marge Be Not Proud," makes it a contender.

As Christmas approaches, Bart becomes frustrated with his mother's smothering ways. When he is told he can't have an expensive and violent video game called Bonestorm, Bart goes ahead and shoplifts it. Unfortunately, he's not particularly smooth about it, and he is banned from the store. Bart manages to avoid having Marge and Homer find out about his crime ... for a while.

Everything unravels when Marge forces him back to the store he is banned from, to take the family Christmas photo in their studio. Initially, she defends her son's reputation — until she's confronted with video evidence that Bart did indeed shoplift.

After that, Marge simply can't look at Bart the same way again. Gone are her mothering ways, replaced by a cold and distant affect. She leaves Bart out of family activities like building snowmen, drinking hot chocolate, and decorating the Christmas tree.

In the end, Bart manages to win his mother's love back. However, seeing it go away completely thanks to one of his many, many crimes is perhaps the most chilling punishment Bart ever received.

Deafening the entire town

"The Secret War of Lisa Simpson" chronicles the aftermath of one of Bart's most damaging pranks. On a field trip to the police station, he gets his hands on 15 megaphones, which, naturally, he lines up and attempts to test. The sound that emerges from the final megaphone in the line is so amplified that it breaks every window in town and leaves a ringing in everyone's ears.

This prank is so destructive, it convinces Bart's desperate family to take Chief Wiggum's advice and enroll Bart in a strict military school. While that obviously doesn't work out, his initial prank with the megaphones marks his most expensive and harmful antic to date. 

Sadly for those wondering if they can teach their own town a thing or two by lining up several megaphones, YouTuber TheBackyardScientist put this to the test in 2017. To mass disappointment, he found that lining up several megaphones does indeed increase the volume, but nowhere near the catastrophic levels that Bart achieves.

Convincing the town a boy is trapped down a well

When Bart receives a microphone that lets him broadcast his voice over the radio, he immediately figures out how he can use it for mischief. "Radio Bart" doesn't just follow the destruction that ensues — it sees him grievously punished for it.

Bart starts by tricking his neighbors Rod and Todd into thinking that God is speaking to them. Then, he ups his game by sending a radio down a local well and convincing the entire town that a young boy named Timmy O'Toole is trapped at the bottom and pinned by a rock.

It doesn't take long before the people of Springfield get whipped up into a frenzy, with musician Sting even joining Krusty the Clown in singing a benefit song entitled "We're Sending Our Love Down the Well." As people start to genuinely worry for Timmy's life, Lisa figures out her brother's ruse and reminds him that the radio has a label with his name on it. 

In a failed effort to retrieve the damning evidence, Bart ends up trapped at the bottom of the well himself. However, now that it's been revealed that he was tricking everyone, it's hard for anyone to see this as anything but justice. It isn't until they're inspired by Homer's desperate effort to dig Bart out that people agree to not let a 10-year-old starve to death.

Putting Homer in a coma

"So It's Come to This: A Simpsons Clip Show" is an episode driven by Bart's desire for revenge. In an effort to get back at his dad after a battery of April Fool's Day pranks, Bart takes one of his beers and uses an industrial-strength paint shaker on it. When Homer cracks it open, it explodes with massive force and seriously injures him. Things take such a turn that Homer is placed in a coma, and the family is told that he may never walk again.

The family, stuck in the hospital, reminisces about old times in what became the series' first clip show. In the end, Bart tearfully confesses to Homer that he's responsible for the beer prank and his subsequent injuries. The ensuing rage, fortunately, wakes Homer up from his coma so that he can strangle Bart. 

The end of the episode reveals that Homer had been in a coma for well over a month, resulting in a loss of brain function. While that might not be noticeable in someone like Homer, it still marks a truly rotten consequence of Bart's tomfoolery.

Ruining Lisa's babysitting career

In "My Sister, My Sitter," Lisa decides to embark upon a career in babysitting. After she successfully watches multiple kids for various Springield families, she is put in charge of Bart and Maggie while her parents enjoy a night together. Bart is, of course, enraged at being babysat by his little sister. He sets out to cause as much mayhem as he can, in an effort to teach Lisa a lesson. After caffeinating Maggie, ordering massive quantities of food by phone, and deliberately misinterpreting Lisa's orders, he and Lisa get in a fight and he is accidentally knocked down the stairs. Though he dislocates his arm and gets a nasty bump on the head, he refuses to go to the hospital — he wants to preserve his injuries to incriminate Lisa.

In the end, Lisa forced to take an unconscious Bart to the hospital. Though she attempts to do this without anyone knowing, she is ultimately found out. Her reputation as a babysitter is ruined, which Bart, after being treated for his injuries, apologizes for. Though the people of Springfield, having the memories of goldfish, end up employing her again, viewers aren't likely to forget the turmoil Bart caused by being a petulant brother.

Almost killing Martin

In "Dial "N" for Nerder," Bart and Lisa are on a hike when they discover Martin excavating arrowheads near a cliff. While Lisa is content to join in on the fun, Bart finds it boring. He steals Sideshow Mel's hair bone and plants it as a prop for Martin to discover. When he does, Bart reveals that he's tied it to a stick, which he raises up, hitting Martin in the head.

While the prank might have seemed harmless, albeit mean, the blow from the bone sends Martin tumbling off the cliff onto a ledge below. Lisa, attempting to rouse him by poking him with a stick, ends up pushing the boy off the cliff entirely, to his apparent doom.

Bart has to be convinced by Lisa not to tell anyone, but is all too eager to agree to just let the presumed murder of their classmate remain a secret. Martin is actually presumed dead for several days, with the school even having a memorial service in his honor. Although it turns out that Martin survived his fall thanks to a special wedgie-proof lining on his pants, the fact remains that another one of Bart's pranks led to serious harm to another person. In addition, it forced Lisa to grapple with the fact that she has a dark and twisted side of her own to contend with.

Destroying Lisa's craft and ruining Thanksgiving

"Bart vs. Thanksgiving" finds Lisa slaving away on a table centerpiece for Thanksgiving, which she proudly presents to her family before dinner. However, they're only able to admire it for a moment before Bart comes in and complains that the large display is taking up too much room and preventing him from putting down the turkey.

The two siblings squabble, and eventually, Lisa's creation is knocked into the fireplace and burnt to a crisp. The family is furious, with Marge even going so far as to declare that Bart has ruined the holiday. Bart is given a second chance to celebrate Thanksgiving with his family, provided he apologizes to his sister. But Bart believes he didn't do anything wrong, and stubbornly chooses to run away from home instead. He hopes, like any child, that his family will realize how wrong they were in the wake of his absence.

This doesn't work on most of the family, and he returns home to ridicule. However, it does appear to work on Lisa, who manages to convince Bart of his wrongdoing. He apologizes, and the siblings make up. 

Blaming someone else for burning their Christmas tree

When Marge orders Bart not to open his Christmas presents until 7 AM, he scoffs — and ends up accidentally setting fire to the entire tree display. Fortunately, he's able to put it out and bury the evidence under snow before the rest of the family wakes up. When they do, he spins a story about a burglar coming into the house and taking all of their stuff.

Not only does this set the town on the hunt for a villainous, non-existent burglar, it prompts the public to donate $15,000 to the Simpson family. While Marge, Homer and Lisa are thrilled with the way the situation turned out, the guilt finally becomes too much for Bart to bear, and he confesses to the family. However, he's too late. As Kent Brockman arrives to do a human interest story on the generosity the family has received, the burnt carcass of the Christmas tree is discovered. Immediately, the Simpsons are painted as a pack of liars.

When the Simpsons are unable to pay the money back or win it on Jeopardy!, the town takes matters into their own hands. They ransack the family home to get their money back in the form of the Simpsons' possessions. Thanks to Bart's behavior, the family is left with just one tattered washcloth.