In a reimagining of Stephen King's novel IT, Bart goes to prankster rehab after a clown-mask prank terrifies the town and destroys Krusty's career. A tortured Krusty then tries his hand at serious drama with a regional theater company. Meanwhile, at Springfield Elementary School, Principal Skinner retires.
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The episode opens with Principal Skinner telling Groundskeeper Willie that he plans to retire, with Martin discovering the secret and blabbing it to the entire school. During the final send off Skinner chose Bart for his final farewell, who attempted to shoot him in the head with a rock. However, it was revealed that the retirement was just a ruse so Skinner would finally blow the whistle on Bart after years of the school getting pranked.
Feeling embarrassed, Bart chose to pull off the ultimate prank to the entire staff by super gluing the faces of Skinner and the staff with plastic Krusty masks. Unfortunately this caused people around Springfield to become terrifed of clowns and also caused Krusty to lose his comedic edge.
Because of the hijinx Krusty is no longer taking as a comedic character, and even lost his clown appearance and look normal (with Homer saying that Krusty looks just like him, and making other "Breaking the fourth wall" reference) Lisa then convince Krusty to turn into a serious actor, and took part are a parody play version of death by a Salesman, written by Llewellyn Sinclair (with his second appearance from A Streetcar Named Marge) who at first couldn't do, until Lieweyin motivate him, causing Krusty to become a serious actor until his clown self appeared telling him that he is still a clown and nothing else.
On the night of the play, Krusty is still being hunted by his former clown self. During the play as Krusty tried to quiet the crowd inside his mind, he cause the audience to laugh realizing that he is not a serious actor but a clown and started to make comedic antics.
Meanwhile, as Bart went to juvie Court and was about to be free with a "boys will be boys" saying, Marge loudly said no as she told the judge that what Bart did was terrible and had a real problem with pranking and suggest the judge to punish Bart, resulting in him going to a rehab center for almost a month. Although Marge think she did a good thing she doesn't know if it really a good thing.
During a session as Bart place tacks on the doctor sit, the doctor convinced Marge to come in and sit on his chair, causing Bart to stop the prank and one step of his treatment.
After being released, Bart went to apologize to the people get pranked on, such as Reverend Lovejoy and Willie. However after revealing a prank that even Willie like, Bart planned to pull the ultimate prank, staging a fake apology announcement at the gymnasium where above the crowd is a net full of water balloons. But when he saw Marge in the crowd, he tries to tell people to run away but the weight of the water balloons broke the net, causing the crowd to get splashed with the water, with Marge finally realizing "that boys will be boys" saying is real and that motherhood stinks, followed by Homer saying the same saying and Marge walking into the boys restroom to get even with Homer.
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