In a reimagining of Stephen King's novel IT, the entire faculty at Springfield Elementary School pranks Bart, forcing him to seek revenge by making them wear clown masks, only to cause the entire town to start fearing clowns, destroying Krusty's career. While a tortured Krusty tries his hand at serious drama with a regional theater company, Marge convinces a judge to send Bart to a rehabilitation camp in order to try to cure him of pulling pranks.
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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 last farewell, who attempted to shoot him in the head with a rock. However, it was revealed that the retirement was just a trick so that Skinner would finally blow the whistle on Bart after years of being pranked by him.
Feeling humiliated and offended, Bart chooses 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, the trick causes people around Springfield to become terrified of clowns, and also causes Krusty to lose his comedic edge.
Because of this activity, Krusty is no longer a comedic character, and even loses his clown appearance and makeup, 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 Krusty 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 silent the voice inside his mind, he causes the audience to laugh and 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 grows a conscience and doesn't understand if it really is 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 tricked 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 sucks, followed by Homer saying the same saying and Marge walking into the boys restroom to get even with Homer.
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