[7.4/10 on a post-classic Simpsons scale] This one has some of the things that would drive most die-hard Simpsons fans nuts. There’s some cruelty and disdain that doesn't go down easy. There’s some overly long gags (like Ned’s song) that afflicted the show at this point. And there’s the fact that the B-story just sort of peters out without any real resolution.
But I appreciate the core of this one, and how it gets the Homer-Bart relationship. More than any other two members of the Simpson family, Homer and Bart get each other, as childish troublemakers who are often interested in and bored by the same sorts of things. But they can also make one another’s lives harder in a lot of ways, and that causes friction and frustration. The way this episode dramatizes that with the two of them going on a road trip to a “boy prison” self-improvement camp is surprisingly good.
You see the friction in Bart ruining Homer’s Vegas trip, or getting him trapped in a diner, or just with Homer talking about the tough parts of his life as a dad. But you also see them making fun of the same dorky (but well-mannered) father and son at that diner, and Homer ultimately realizes that he loves his son too much to subject him to that sort of “tough hate” environment. There’s questions to be asked about enablement and how to really help Bart which are probably deeper than makes sense for a half-hour sitcom. But still, I like that this is, at heart, a Bart-Homer episode and takes that serious.
The B-story, with Marge inadvertently making up for her failing garage sale by selling Homer’s expired pain pills, is mostly just there. There’s the occasional good gag (the dog’s reaction to Lisa, for one), but for the most part, there’s not a lot of good gags and the story just sort of disappears.
That said, I kind of love the ending. I know the lack of resolution and winking finish is the kind of thing that will drive big Simpsons fans nuts, but I do get a big kick out of Marge and Homer ending up in jail and Lisa remarking that somehow she always knew it would come to this.
Overall, this one definitely has flaws, but it gets the core Homer-Bart relationship right, which is the focus of the episode, and that counts for a lot.