Bart goes to prankster rehab after a clown-mask prank terrifies the town and destroys Krusty the Clown's career. A tortured Krusty then tries his hand at serious drama with a regional theater company.
- Defensive Feint Trap: Skinner only pretended to retire to lure Bart out in the open so he could pull a prank on him. Bart is only pretending to repent so he can pull a prank on those he "apologizes" to.
- Even Bad Men Love Their Mamas: Bart has second thoughts about his pranks whenever his mother risks being hurt by them.
- Falsely Reformed Villain: Bart is only pretending to regret being a prankster to reunite people where he can drop water balloons on them.
- Kick the Son of a Bitch: Skinner deflects Bart's shot with a lid, which then bounces off and knocks out his abusive mother Agnes.
- The Man in the Mirror Talks Back: Krusty starts seeing his old self telling him that he's going to fail as a serious actor. He also sees his father Herschel.
- Monster Clown: Bart's prank is to glue clown masks on the teachers' faces, causing everyone who sees them to be scared. There is also a guest appearance by Pennywise.
- Parody: "The Salesman's Bad Day" is a parody of Death of a Salesman.
- Self-Deprecation: Upon seeing Krusty without a clown face, Homer realizes Krusty looks like him. He also notices that "Maggie looks like Lisa" and Milhouse's parents look like each other.Homer: Why is this universe so lazy?
- Shout-Out: The subsequent strings of encounters resulting from Bart's pranks references the real life plague of clowns appearing throughout 2016. The 2017 incarnation of Pennywise also appears, referencing the belief the stunts were part of a promotional tactic for the film.
- Tar and Feathers: Skinner's prank on Bart is to cover him in honey and birdseed, then get attacked by crows.
- Thumbtack on the Chair: Bart tries to pull this on the psychologist, but he turns the tables on him by asking Marge to take his seat instead.