Fred Armisen and Carrie Brownstein from Portlandia guest star as cool neighbors whom Homer wants to emulate, and Marge and Bart find to be pretentious hipsters whose ilk are overrunning the town.
- Donut Mess with a Cop: Chief Wiggum moved the local police force to find a new donut supplier and threatened to shoot him to force him to make a new batch.
- Hipster: The cool neighbors. They then had more people join in order to spite Homer and Marge.
- Deconstructed. When the fire breaks out due to Terrances compost heap, and the fire fighters cant get to it due their old time horse drawn fire engine losing its horse.
- Further deconstructed in their son T-rex, who is grouchy and unpleasant due to not getting much sleep from his 'cool' activities, and not only resents a lot of the things he has to do but expresses a desire to be able to watch TV and eat fast food like a normal kid.
- My God, What Have I Done?: Chief Wiggum once he realized he was threatening to shoot somebody for donuts. He said he knew there was something wrong with him because it was the second time in a day he played that trope. The first time's details have never been discussed.
- The Only One Allowed to Defeat You: Invoked. Bart has a disagreement with T-rex when Homer put the effort to make him a jacket with a dinosaur wearing sunglasses and saying "Dino-cool" on the back that T-rex found lame. Bart scolds T-rex for throwing the gift to the trash, but mostly because Bart is only allowed to insult Homer.
- Squick: In-Universe. Marge can't stand breastfeeding and quickly is labeled as weird by the other cool mothers.
- Status Quo Is God: When Springfield is declared "America's Coolest City" by the New York Times, the hipsters take it as a sign the town is "played out" and decide to leave.