- Catharsis Factor: Seeing Homer steal a jackhammer and use it to violently destroy the boot on his car, is rather satisfying after the Humiliation Conga he endured before that point. The damage it does to his car almost seems Worth It.
- Darkness-Induced Audience Apathy: There are many people who dont find the fact that the episode consists of Homer going through a Humiliation Conga for an entire day to be enjoyable.
- Franchise Original Sin: A holdover from Season 8, Homer's Jerkass behavior in this episode may have began his eventual Flanderization.
- "Funny Aneurysm" Moment: The infamous "They stick all the jerks in tower one!" line, followed by the men in opposite buildings arguing rudely with each other until a third interrupts them, revealing all three men were jerks.
- Bart's line from the Statue of Liberty: "Hey immigrants, beat it, the country's full!" got a lot less funny following the 2016 presidential election.
- Hilarious in Hindsight:
- As punishment for his car being left in New York City, Homer's car will be thrown into the East River, which was known for its parasitic and hazardous conditions in 1997. Nowadays, the river has been cleaned up considerably and ironically enough, it would be far worse to throw it into the Hudson River, whose quality has severely declined in the years since this episode first aired.
- When at MAD Magazine headquarters, Bart sees Alfred E. Newmannote talk about a spoof called "The New Kids on the Blecch". Three-and-a-half years later...
- Jerkass Woobie: While this episode portrays Homer very unpleasantly and marked the point in the show where he would become Flanderized into an unrepentant Jerkass, his behavior is pretty understandable here because he has a really rotten time in New York.
- Values Resonance: The Betty Ford Clinic musical about celebrities going to rehab for their erratic, criminal behavior is still relevant today, thanks to the likes of Britney Spears, Lindsay Lohan, Charlie Sheen, Amanda Bynes, Tara Reid, Paris Hilton, and others getting the same treatment (in fact, the main character of the musical even looks a little like Charlie Sheen, even if he was based on Robert Downey Jr.).
YMMV / The Simpsons S 9 E 1 The City Of New York Vs Homer Simpson