Although the whole family is beloved by the fanbase now, when The Simpsons first premiered, the breakout character that scored landmark ratings for the series was Bart. The term “Bartmania” was coined to describe the eldest Simpson child’s widespread popularity. Entertainment Weekly called Bart the “entertainer of the year” in 1990, while Time magazine named him as one of the 100 most significant people of the 20th century.
From a job with the mafia to a run-in with a murderer to a prank gone wrong involving a walkie-talkie in a well, Bart has been at the center of some of The Simpsons’ best episodes.
10 Radio Bart (Season 3, Episode 13)
Bart is initially disappointed when Homer gives him a karaoke microphone for his birthday in season 3’s “Radio Bart,” but changes his mind when he realizes he can use the microphone for pranks.
He lowers the speaker down a well and pretends to be a little boy trapped down there, galvanizing the whole town to lift the spirits of an imaginary kid. When Bart himself gets stuck down there and reveals the trick, the rescue team isn’t so eager to help him out.
9 Bart The Murderer (Season 3, Episode 4)
Fat Tony hires Bart to work as a bartender for the mob in season 3’s “Bart the Murderer,” and it doesn’t take long for the mischievous prankster to fit right into the mafia lifestyle.
This episode marked the first of many appearances by Fat Tony and his goons. There are plenty of references to gangster movies like Goodfellas, The Godfather, and A Bronx Tale.
8 Itchy & Scratchy: The Movie (Season 4, Episode 6)
A movie adaptation of Itchy & Scratchy hits theaters around the same time that Marge is pressuring Homer to give Bart punishments that actually stick. In a moment of rage, Homer forbids Bart from ever seeing Itchy & Scratchy: The Movie.
Bart does everything he can to see the movie, which breaks all kinds of records and is described by Lisa as the greatest movie ever made, and Homer finally lets him see it in a heartfelt flash-forward sequence set in the future.
7 Boy Scoutz N The Hood (Season 5, Episode 8)
Bart joins a Boy Scout troop by accident in season 5’s “Boy Scoutz N the Hood,” but warms to the troop when he finds out he can get out of school to go to meetings with his scout leader, Ned Flanders.
When he goes on a father-son camping trip, Homer gets them all stranded at sea, gorges all their food rations, and bursts the raft — only to discover a Krusty Burger on an oil rig at the last second.
6 Brother From The Same Planet (Season 4, Episode 14)
After Homer forgets to pick up Bart from his soccer practice in the pouring rain, Bart disavows his father and calls up a “big brother” program to get another male role model sent in his place.
In response, Homer applies to the program and gets his own “little brother.” It all culminates in an epic fight between Homer and Bart’s big brother.
5 Bart’s Girlfriend (Season 6, Episode 7)
Meryl Streep guest-starred as Reverend Lovejoy’s daughter Jessica in season 6’s “Bart’s Girlfriend.” Bart quickly falls for her and tries unsuccessfully to shed his “bad boy” image to impress her. However, she turns out to be even worse-behaved than him, so they hit it off.
As the relationship progresses, it becomes clear that Jessica is just using the spell she has over Bart to manipulate him and Lisa tries to free him from the trance.
4 Cape Feare (Season 5, Episode 2)
Sideshow Bob has been in a bunch of great Bart-centric Simpsons episodes (and a couple of not-so-great ones), but easily the best is season 5’s “Cape Feare,” which spoofs Martin Scorsese’s remake of Cape Fear with Bob taking the place of Robert De Niro’s Max Cady.
From Bob’s endless rake-stepping nightmare to Homer terrifying Bart by showing him his new chainsaw and hockey mask in the middle of the night, “Cape Feare” is filled with classic moments.
3 Bart Gets Famous (Season 5, Episode 12)
When he gets a job as an intern on Krusty’s show, Bart is given one line to say because they’re about to go live and the actor hasn’t shown up. He accidentally destroys the whole set on live TV and says, “I didn’t do it.”
The catchphrase makes him an overnight sensation and Bart has to contend with the foibles of fame and only being popular for repeated use of a single phrase.
2 Bart Sells His Soul (Season 7, Episode 4)
Bart and Milhouse are tasked with cleaning the church organ after the latter folds and snitches on the former for a prank. They debate the existence of the soul, which is preached by every single religion, and to prove that there’s no such thing as a soul, Bart sells his to Milhouse for a couple of bucks.
Then, strange things start happening and Bart becomes desperate to get his soul back. The episode also has a hilarious B-plot as Moe tries to retool his bar as a family restaurant.
1 Bart’s Comet (Season 6, Episode 14)
Principal Skinner punishes Bart for a prank by forcing him to come along to his early-morning astronomy. Skinner is desperate to make a discovery but hasn’t had any luck. Then, when he’s distracted, Bart discovers a comet, reports it, and gets it named after himself.
However, the comet turns out to be hurtling toward Springfield, ready to wipe out the entire town, so the townspeople get into panic mode as they try to figure out a solution.
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