Boy's Town is some kind of correctional facility for misguided youths.  Crazy Town isn't anything, so it's just a bit of clever wordplay.

[Boy’s Town](https://en.wikipedia.org/wiki/Boys_Town_\(organization\)) refer’s to the orphanage.

The writers were so impressed with themselves on the DVD commentary for that episode, so I guess there's more to it. What's "Boys Town" referring to, and what's "Crazy Town" referring to, beyond the context of Bart/Hugo being a boy and crazy?

Can someone explain this joke: Too crazy for boys town, too much of a boy for crazy town.