Following a string of advertising-based hallucinations, Homer impulsively decides to go to clown college and become a Krusty impersonator. Meanwhile, the real Krusty is trying to dodge the Mafia after making some bad bets.
- Affably Evil: Don Vittorio DiMaggio apologizes as he is about to shoot Homer (believing him to be Krusty) and decides he won't do it on the condition of having the "Spin-Cycle Fantastic" trick performed for him (which Homer fails); then apologizes again when the real Krusty shows up at the last second, and ultimately lets them both live when they successfully pull off the trick together.
- Arson, Murder, and Jaywalking: Homer's reasons why it sucks being a clown: "You get kicked by kids, bit by dogs, and admired by the elderly."note
- Chekhov's Skill: Inverted; it's Homer's inability to ride a mini bicycle through a loop that resurfaces -and almost gets him killed- by the end of the episode.
- Comically Missing the Point:
- While all the other clown college students inform Krusty where they're from, Homer just says his name.
- After Krusty reads the joke names of certain towns, Homer inexplicably finds the most normal one, Seattle, to be hilarious.
- Homer beats up an actor, portraying a burglar to amuse the children in the audience, not understanding that it's obviously an act.
- After Krusty obviously runs out on them, Legs says he needs to use the bathroom next. This causes Fat Tony to roll his eyes.
- Department of Redundancy: Homer: "Who am I clowning? I have no business being a clown! I'm leaving the clowning business to all the other clowns in the clowning business."
- Digging Yourself Deeper: As Homer tries to tell Fat Tony he isn't Krusty, everybody he tries to say he is, including himself, has upset Tony one way or another.
- Even Evil Has Standards: After nearly being killed for not paying his debts Krusty pays the money anyway, which turns out to be the ridiculously low sum of $48. The boss is happy and even gives him back his change.
- Family-Unfriendly Violence: The scene where the Krusty Burglar is beaten up.
- Idle Rich: Krusty lights a cigarette with a one dollar bill (later also with an original Superman comicnote and a pearl necklace), then orders his assistants to "Put five thousand bucks on the Lakers. Hire Kenny G to play for me in the elevator. My house is dirty; buy me a clean one."
- Imagine Spot: Homer's obsession over joining Clown College.
- Is It Something You Eat?: When Homer goes by the new billboards, the first few ones are of food, so when he comes to the one for Clown College, he complains "Clown college? You can't eat that!"
- Kill the Cutie: An Estonian little person (not the one who played Lisa in the fake video of The Simpsons talking about how they don't miss Bart, though he does have the same voice as him), dressed up as a thief character to amuse the young audience is brutally beaten to pulp by Homer, who doesn't get that it's supposed to be an act.Kid: (crying) Stop! Stop! He's already dead!
- Let Me Get This Straight: One from Krusty's accountant.Accountant: Let me get this straight; you took all the money you made franchising your name and bet it against the Harlem Globetrotters?!Krusty: Oh, I thought the Generals were due!
- Made of Iron: Homer comes out of the botched parachute landing and falling very fast through the giant prop hamburgers with nothing worse than a slightly drunk-sounding Krusty laugh.
- The Magazine Rule: Krusty apparently enjoys reading "Gigantic Asses" magazine and his love of porno magazines helped Apu keep the Kwik-E-Mart in business during its first year.
- National Stereotypes: Don Vittorio acknowledges himself to be one.Don Vittorio DiMaggio: Grazie. Grazie. You have brought great joy to this old Italian stereotype.Legs: No, no, Don Vittorio. You're not -Don Vittorio DiMaggio: Yes, I am. I know it. I am.
- Noodle Incident: When did Homer crash his car into the wall of the Springfield Mafia's club? And, for that matter, when did Barney Gumble take pictures of one of the mobster's sister?
- Plagiarism in Fiction: Krusty is phoned by George Carlin for stealing his "Seven Words You Can't Say On Television". Krusty gives him ten grand, but sarcastically says "Well, excuuuuse me!", causing him have to pay another ten grand to Steve Martin.
- Plot Hole: Milhouse really had no reason to gloat about having Krusty over at his party — Bart already had Krusty over for dinner at his place in "Like Father, Like Clown" (and Milhouse was at the Simpson house with Krusty, so that's really bad that the writers would make Milhouse out as a braggart).
- Pocket Protector: Two of them save Flanders from being killed by Mafia hitmen trying to hit the man standing next to him.*Gunshot* (Flanders is knocked down)
Ned Flanders: Whew, good thing I always keep a Bible next to my...
* Second gunshot* (Flanders is knocked down again)
Ned Flanders: Whew, luckily I was wearing an extra large piece of the True Cross today.
(Flanders notices that he doesn't have any other religious symbols with him)
Ned Flanders: I think I'll go inside.
- Punbased Title: "Homey the Clown" was a character from the sketch show In Living Color!.
- Rich in Dollars, Poor in Sense: The reason Krusty founds a clown college is because he risks bankrupting himself with his extravagant spending.
- Krusty bets against the Harlem Globetrotters, and of course loses!
- The scene where Krusty has plastic surgery is a shout-out to the Twilight Zone episode "Eye Of The Beholder".
- Homer and Krusty drive a mini bicycle together, causing Homer's head to bump against some glasses and quote the theme from The Godfather.
- Homer building a circus tent with his mashed potatoes while his family looks at him with a concerned look is a parody of a similar scene in Close Encounters of the Third Kind, where the protagonist's obsession about a certain mountain hill also makes him create one with a spoon and some porridge.
- Homer says to his kids that they didn't complain when he dressed up as Tom Bosley and got them "this close to Chachi".
- Dick Cavett mentions he knew Woody Allen, though nobody in the audience cares. When he tries to make conversation with Homer and says his "churlish attitude reminds me of the time I met Groucho" Homer threatens "you'll be dining with Groucho tonight if you don't shut up!"
- The son of the guy who played Huggy Bear in Starsky & Hutch accepts Krusty's award.
- Single Malt Vision: One of the mobsters sees double: four Krusties!
- Special Guest: Johnny Unitas and Dick Cavett.
- Tempting Fate: After buying all of the consumer products advertised on the latest billboards, Homer claims he's not enrolling in the Clown College since the billboard he saw had no affect on him. Soon after he says this, he starts hallucinating clowns, and it continues until he finally decides to enroll.
- Trapped by Gambling Debts: Krusty's story arc in this episode.
- What, Exactly, Is His Job?: In this episode we learn Milhouse's father works at the cracker factory (later, in "Bart On the Road," we find out that Kirk oversees production on crackers, and "A Milhouse Divided" implies that Kirk is a managernote whose incompetence sent the factory into a tie in sixth with with Table-Time and Allied Biscuits).
- Writing Around Trademarks:Bill: "At this rate you'll be broke in a month. The only thing left to do is...open a Clown College and train some regional Krustys."Krusty: "You mean like that bozo, Bonko the Clown?"