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 sendoff, Skinner chooses 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 being pranked by him.
Feeling embarrassed and outraged, Bart chooses to pull off the ultimate prank to the entire staff by super gluing the faces of Skinner and staff with plastic Krusty masks. Unfortunately, this causes people around Springfield to become terrified of clowns, and also causes Krusty to lose his comedic edge.
Because of this, Krusty is no longer a comedic character, and even loses his clown appearance and make-up, with Homer saying that Krusty looks just like him. Lisa then convinces Krusty to turn into a serious actor, and takes part in a parody play version of Death by a Salesman, called The Salesman's Bad Day, written by Llewellyn Sinclair (with his second appearance from A Streetcar Named Marge) who at first couldn't do, until Llewellyn Sinclair motivates him, causing Krusty to become a serious actor until his clown self appears in his mind, telling him that he is still a clown and nothing else.
On the night of the play, Krusty is still being haunted by his former clown self. During the play, as Krusty tried to quiet the voice inside his mind, he causes the audience to laugh. He realizes that he is not a serious actor, but a clown, and starts to do comedic antics.
Meanwhile, Bart is in court and was about to be free with the "boys will be boys" saying, until Marge objects and tells the judge that what Bart did was terrible and he has a real problem with pranking and suggests the judge punishes Bart, resulting in him going to a rehab center for almost a month. Although Marge thinks she did a good thing, she doesn't know if it really a good thing herself.
During a session, as Bart places tacks on the doctor's chair, the doctor convinces Marge to come in and sit on his chair, causing Bart to stop the prank and completing one step of his treatment.
After getting released, Bart goes to make apologies to the people whom he pranked on. However, with the encouragement of Willie, Bart plans 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 observes Marge in the crowd, he tries to tell everyone to run away but the weight of the water balloons breaks 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 her husband.
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