The Simpsons 10 Most Shameless Things Bart Ever Did

The Simpsons: 10 Most Shameless Things Bart Ever Did

Bart Simpson is a ten-year-old mischief-maker who’s pulled some crazy stunts. Here are his wildest antics on the longest-running animated series ever.

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The Simpsons 10 Most Shameless Things Bart Ever Did

Bart Simpson isn’t exactly known for his mild-mannered politeness and well-intentioned charm. In fact, back in the early ’90s, he was the poster boy for the misled, mischievous youth. Armed with a slingshot and an attitude, Bart was as full with more misdemeanors than quippy one-liners.

While we often see Bart facing up to his actions (sometimes with genuine regret), we’ve also seen the spiky-headed kid really make some bold, questionable decisions. Here is The Simpsons: 10 Most Shameless Things Bart Ever Did.

10 Connected All Of The Police Station Megaphones

The Simpsons 10 Most Shameless Things Bart Ever Did

Bart might have calmed things down a little now, but back in Season 8, he was as bold as ever. On a school trip to the Springfield Police Department, Bart thought it wise to connect a string of megaphones (on full blast) together and mutter “testing.”

As you might expect, things didn’t go well, and a sonic shockwave shattered Springfield and every pane of glass within it. Sending Bart straight to military school was the only option left for Homer and Marge, but his intensive regime didn’t really do a lot to interfere with his behavior for the next 22 seasons — and counting.

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9 Bought A Massive Factory For A Dollar

The Simpsons 10 Most Shameless Things Bart Ever Did

Still firmly housed within Season 8, Bart used his unparalleled confidence to bid a singular dollar in an auction for a factory — and won it. His dilapidated green acquisition was as run-down as you can imagine, but it didn’t stop him and Milhouse from wreaking havoc within until it collapsed into rubble on Milhouse’s watch. You’d think that having your name on the documents of a huge, collapsed factory would have some legal repercussions, but apparently not, as Bart never mentioned his purchase again.

8 Made The “Angry Dad” Cartoon

The Simpsons 10 Most Shameless Things Bart Ever Did

Considering he has spent an eternal youth being strangled by his father, it’s a surprise that it took 13 seasons for Bart to finally draw him as a rampaging Hulk-like character.

When he finally did, it spawned the iconic “Angry Dad” cartoon, much to the dismay of Homer, who proceeded to strangle Bart once more. Despite the ballsy move of making a website centered on his abusive father into the “most popular non-pornographic website of all-time,” Bart manages to get away with this one by actually helping Homer get the anger management help he needs. While it’s a very shameless move, things end up okay for the pair.

7 Tried To Become “President In Charge Of Keeping It Real”

The Simpsons 10 Most Shameless Things Bart Ever Did

Noticing that Lisa may not be the coolest President around (this episode is set 30 years in the future, with Lisa as the U.S/ President, and Bart a 40-year old slacker), Bart suggests he be made “President In Charge Of Keeping It Real.”

The shameless Bart would not only be happy to be known to the world under this bizarre guise, he even thinks he got the job. That is, until Billy Carter’s ghost appears to him to explain otherwise. It seems to work and Bart ends up realizing Lisa is just trying to keep him out of her presidential hair.

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6 Shot A Mother Bird

The Simpsons 10 Most Shameless Things Bart Ever Did

One of the more genuinely heart-wrenchingly shameless Bart Simpson moments comes from “Bart The Mother,” the final episode writing by David Cohen before he left for Futurama. While hanging out with the part-bully, part-friend (we never really know where these two stand, to be honest) Nelson Muntz, Bart shoots and kills a bird. Sure, he didn’t mean to, but simply pulling the trigger was a pretty impudent move. With the bird actually sitting on a nest of lizards, Bart somehow ends up twisting the scenario on its head once more by introducing pigeon-killing lizards to Springfield and receiving a loganberry-scented candle as a reward from Mayor Quimby.

5 Became Krabappel’s Fake Woodrow

The Simpsons 10 Most Shameless Things Bart Ever Did

Managing to convince your teacher that you, a ten-year-old boy she sees every day, are in fact a middle-aged love interest is an impressive feat. But laughing while watching her excitedly wait for a date he knows doesn’t exist is genuinely hard to watch.

Of course, as ever, Bart realizes his mistake and sends her a poetic breakup letter to ease the pain. It’s a nice touch, but continuing the charade is arguably even more brazen than before, and this time he gets Lisa involved. It’s also pretty likely this entire harebrained scheme has impacted the lovelorn Principal Skinner in the process.

4 Pretended To Be Stuck Down A Well

The Simpsons 10 Most Shameless Things Bart Ever Did

“Radio Bart” gave us one of the greatest songs in The Simpsons history, “We’re Sending Our Love Down The Well,” with Sting singing alongside Krusty The Clown and a whole host of celebrities.

The complex series of events that led to this track, however, all start with some more exceptionally shameless moves from Bart. He lowers a radio down a well, invents an alter ego called Timmy O’Toole, and pretends to be him via a microphone he got for his birthday. This is a rare scenario in which Bart actually does get his comeuppance, and he’s left in the well until Homer digs him out.

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3 Once Stole A Copy Of Bonestorm

The Simpsons 10 Most Shameless Things Bart Ever Did

After being rejected by Milhouse (who is playing under the name “Thrillhouse” in this episode) Bart decides he needs to work out a way to get his hands on the Bonestorm video game.

Despite being just ten years old, Bart manages to work up the confidence to shoplift the game from the huge Try-N-Save store in Springfield. It doesn’t quite go according to plan, and when the Simpson family returns to the store, Bart is quickly ejected, losing the love of Marge soon after. Of course, he wins it back eventually, but he forced himself into a tough few days following this bold move.

2 Sold His Soul To Milhouse

The Simpsons 10 Most Shameless Things Bart Ever Did

As audacious as he is, you’d expect Bart to have a certain regard for his soul. Though it seems not, as he sells it (scribbled on a piece of paper) to Milhouse during this Season 7 episode. Bart regrets his decision pretty quickly and returns to Milhouse to desperately bargain with him. Despite eventually getting his soul back through Lisa, Bart hasn’t learned a lot, and simply eats the piece of paper while she lectures him.

1 Accidentally Became Famous

Bart kicks off “Bart Gets Famous” by sneaking away from a school trip into the Channel 6 TV studio, where he somehow lands himself a job as Krusty’s assistant. This jettisons Bart to an appearance in a sketch, where he utters the immortal line “I didn’t do it” and becomes a world-famous megastar. This all comes from the one bold move of everyone’s favorite yellow ten-year-old. It also has quite a poignant meaning, allowing Bart to represent the concept of catchphrases and their relevance to The Simpsons.

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