- Harsher in Hindsight: One scene has Homer and the rest of the Neighbourhood Watch utterly fail to use their firearms responsibly, with several guns going off in the middle of Homer's speech to a concerned Marge about how they can be trusted. A later episode, "The Cartridge Family", would have Homer engaging in Reckless Gun Usage to the point that Marge leaves him and takes the kids for their own safety. For bonus points, the final straw comes when Homer lies to Marge about having gotten rid of the gun and Bart finds it and nearly shoots Milhouse with it; Bart is one of the people holding a firearm in this episode.
- Magnificent Bastard: Molloy is a resident of the Springfield Retirement Castle who moonlights as the Springfield Cat Burglar. When Homer, head of the new Neighbourhood Watch, was interviewed by Kent Brockman, Molloy phoned in to taunt Homer that he would steal the Springfield Museum's Zirconia and succeeds despite Homer's efforts. When arrested, Molloy gracefully returns all his stolen goods before being put in jail, where he tells Homer and Chief Wiggum about where he hid all his stolen loot, leading to the whole town hunting for it. When the location Molloy described is found, all that is present is a note saying Molloy lied and used the time they spent searching to escape. An archetypical Gentleman Thief, Molloy remains memorable despite his only appearance and relatively humble goals.
- Suspiciously Similar Song: The cat burglar's musical theme is a copyright-friendly version of The Pink Panther theme music, and the final stretch of the episode features the trope applied to the music from It's a Mad, Mad, Mad, Mad World.
- Unintentional Period Piece:
- The scene where the kids mistake Homer for MC Hammer firmly dates the the episode to the early 90s, when Hammer was still considered a household name prior to his notorious fall from grace into the Butt-Monkey of the hip-hop world.
- The gag about the saxophonist being chased by the vigilantes because he purchased the saxophone at Sears (and they began the encounter thinking that the saxophone is Lisa's stolen instrument) shows the episode was done during the time that Sears was still a sales giant instead of a dying brand (with only 13 stores left overall - 12 in the U.S. and one in Puerto Rico - as of January 2024).
- Values Resonance: The residents of Evergreen Terrace form a neighborhood watch group, which under Homer's leadership quickly turns into a Vigilante Militia in all but name. This had already been a problem going back several decades, but it especially struck a chord in the 2010s, where there was increased awareness of "neighborhood watch" groups that for all intents and purposes are actually vigilante gangs dedicated to keeping people the residents deem undesirable out of their neighborhood.
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