Y'all are talking about "The Wandering Juvie," which is from season 15. I actually quite like season 15--I know I've said elsewhere that it's probably the last half-decent season of the show--and I remember being quite fond of that particular episode when it first aired, but Josh is right that the guest star du jour (Sarah Michelle Gellar) is really bland; however, the episode does also feature Charles Napier, who is awesome, so maybe it balances out. Though "The Wandering Juvie" is
also a Bart Gets a New Love Interest episode, a genre of episode I find particularly loathsome (with the exception of "Bart's Girlfriend"), so maybe Josh is in fact right that it is crap: in any event, it's not the best thing that particular season has to offer.
And speaking of season 15, they also did a Homer Goes to Jail episode that year, if you count "The Ziff Who Came to Dinner" (also a meh-ish outing). And, hell, if you want to get technical--which, I mean, who doesn't?--"One Fish, Two Fish, Blowfish, Blue Fish" is the original Family Member Goes to Jail episode, what with Homer needing to be bailed out by Barney's usually-unacceptable rusty money.
I mean, I didn't see this apparently lousy rehash of "Marge in Chains," so I can't speak to that episode specifically--I just figured this was a good opportunity to be all pedantic about Simpsons miscellany, which I need to do once in a while to maintain my dorky street cred.