Bart cuts off the statue head of Jebediah Springfield to be cool at some bullies, but the city gets outraged and starts looking for the vandal.
The episode depicts flashback scenes where it begins with Homer and Bart walking on a sidewalk in downtown Springfield at nighttime. Bart has the head of a statue in his arms. As the pair turn the corner a furious mob advances on them. Homer and Bart are forced to turn and flee. Then the mob corners Homer and Bart in the town square next to the headless Jebediah Springfield statue. As the mob slowly advances, Bart climbs onto the statue and begs everyone to listen to his story.
While the rest of the family prepare to go to church, Homer is preoccupied with a football game. On the way into church, Marge confiscates Bart's portable radio with earphones and gives them to Homer. During Sunday school, the teacher and students discuss the topic of who is allowed in Heaven. Back in the church, the sermon is about sports gambling; Homer is oblivious because he is using Bart's headphones to listen to the game. On the way home from church Marge expresses her disapproval of Homer's headphones and Bart sees that the movie theater is playing “Space Mutants 4”. As Bart wants to see it, Homer doesn't care but Marge refuses. Homer gives Bart $5 and he heads to the theater on his skateboard. Upon arrival, he encounters Jimbo, Dolph, and Kearney (although Dolph will not be named until Season 4). When Bart makes a good impression on Jimbo, the trio invite him to sneak into Space Mutants 4 with them.
After the manager kicks the boys out of the movie theater for not paying, they go to Kwik-E-Mart, where Jimbo, Dolph, and Kearney shoplift several goods even as Bart buys Squishees. Bart meets with them in the parking lot and realizes he was used as a distraction to help them steal from the store, and in an effort to stay cool with the group he doesn't say anything. They wander over to the town square to throw rocks at the statue of the town's founder, Jebediah Springfield, once again Bart goes along with the group so they will like him. After throwing the rock, Mr. Dandy tells them off and the four are scared away. Later while the group lays at the Grassy Hilled Area, while watching clouds one of the kids says it would be cool if somebody cut the head off of the statue. When Bart hears this he defends Jebediah, and then the other three ridicule and tease him for it. Bart walks away embarrassed. When Bart walks home by himself he passes by the statue again, and after thinking about what the kids said earlier he gets an idea. Bart arrives home and talks to Homer in the kitchen about the importance of being popular. Homer tells Bart that no matter what it takes popularity is the most important thing in life. While The Simpsons are asleep, Bart, disguised in a ninja outfit, heads to the town square and climbs to the top of the statue decapitates Jebediah using a hack saw.
The next morning Bart wakes up in bed next to the head of Jebediah (an homage to “The Godfather”). Bart heads downstairs to the kitchen with the head in his backpack where everyone is eating breakfast when a report comes over the radio announcing the decapitation of the town statue. Bart starts get nervous when he sees how everyone in the family becomes angry after hearing the report. Scenes from Moe's bar and the Springfield retirement home reveal that everyone else is upset about the statue as well. In town Bart meets up with Jimbo, Dolph and Kearney and is about to show them the head when he hears them say they were just kidding about decapitating the statue and would like to pound whoever stole Jebediah's head. Bart quickly picks up his backpack and hurries away toward home, passing through a growing angry crowd downtown. On the way, Bart's guilty conscience talks to him in the form of Jebediah's voice. Back at home Bart quickly goes to the back yard and tries to bury the head, but his guilty conscience, acting as Jebediah, talks him out of it. Bart walks in with the head and confesses, much to the shock of the family. When Bart tells Homer he stole the head to become popular, Homer realizes he is at fault as well. Homer and Bart head back into town with the head.
The story ends where the episode began, with Homer and Bart trying to return the head and being chased by the mob. Bart is ready to face whatever punishment that citizens have in store for him, but points out that it wasn't until the head was gone that everyone realized that they had taken the town's heritage for granted and also tells everyone that his guilt outweighs any punishment they might have in store for him. Moved by his words, the townspeople chose to allow Homer and Bart to return the head. As he does, Bart asks the head for forgiveness, and he hears Jebidiah's voice granting it.