Original air date: 3/29/2004 (produced in 2003)
Production code: FABF-11
Bart gets sent to juvenile hall, where he is dragged into escaping with a female prisonmate (played by Sarah Michelle Gellar).
Tropes:
- Aborted Arc: Homer becomes a prison guard to protect Bart a few minutes into the episode, but this is completely forgotten after Bart breaks out and Homer makes no mention of it when he reappears at the end.
- Artistic License – Law: When Homer becomes a prison guard, he gets a gun. In real life, prison guards don't carry firearms due to the possibility of inmates being able to grab them and use them against guards or other inmates. Only personnel in the guard towers have firearms, since inmates are highly unlikely to be able to get to the towers to grab them.
- Ass Shove: Gina threatens Bart with this using a pinecone to stop him calling for help during the breakout.
- Aw, Look! They Really Do Love Each Other: Bart is confused as well as annoyed by Gina's constantly-changing attitude towards him, but when he finds out that, unlike him, she doesn't have a family as he had previously thought, he organizes a Mexican food feast in her cell at juvenile hall with the rest of his family, something she appreciates.
- Bait-and-Switch: At the end of the episode, the Warden sees Gina and the Simpsons about to enjoy a family dinner. He muses about the lonely night he's planned for himself. Marge invites him to join them, but he blows them off, re-iterating he has plans.
- Bears Are Bad News: Chief Wiggum gets mauled by a bear, which is arrested at the end of the episode. Cletus even whittled this event before it happened.
- Belligerent Sexual Tension: The Puppy Love equivalent, anyway. Bart is confused and angered by Gina's Loving Bully behavior (and still thinks Girls Have Cooties) but is suckered into going along with her escape when she kisses him.
- Butt-Monkey: Bart in juvenile hall. Every time he tries to find somewhere to go or something to do, he realizes he can't go there or do it because he will get beaten up, so he decides to hang out by the fence to the girls' juvie. Unfortunately, this gets his uniform sliced up.
- Call-Back: Judge Constance Harm successfully sends Bart to juvie hall, which she tried to do back in "The Parent Rap"
- Chained Heat: Bart and Gina end up like this during a juvie hall dance. It's the reason Bart is forced to go along with Gina when she escapes. When they find a blacksmith to get them out of their cuff, they have to get in line behind a bunch of similarly-afflicted duos, including a nun chained to a hooker and the Sea Captain chained to an octopus.
- Double Standard: Abuse, Female on Male: Gina slices up Bart's uniform when they first meet, and punches him numerous times throughout the episode. Averted when, near the end, she attacks Bart one time too many, and, having had enough, he fights back.
- Everyone Has Standards: Mayor Quimby declares himself an abomination once he's told that the girl he took with him to Bart's fake wedding is his niece.
- Failed a Spot Check: Bart fails to see Chief Wiggum being mauled by a bear near him as he decides to go back and find Gina.
- Foreshadowing:
- Cletus demonstrates the ability to foresee events before they happen and whittles them out in little wooden statuettes. One such scene portrays Chief Wiggum getting attacked by a bear. This later comes true as a Funny Background Event.
- After Gina slices up Bart's uniform, she turns her head to look at him as he is walking away.
- Seymour and Edna are seen planning their wedding, a setup for the next episode. Their argument also makes it obvious that it's not going to work out.
- Genius Ditz: Cletus. He's a hillbilly and definitely not the sharpest knife in the drawer (he was dumb enough to drink out of a thermometer), but he's a good observer and whittles what he sees, so he's able to help Chief Wiggum in tracking down Bart and Gina. He's also able to whittle the future, in particular Chief Wiggum getting mauled by a bear, which comes true later.
- Girls Have Cooties: Bart names his imaginary wife "Lotta Cooties" as part of the wedding scam, and later states that girls are "icky-pants". Gina tells him there's no such thing.
- Groin Attack: When Gina slices up Bart's uniform, she implies she will castrate him by saying his "puberty will be very boring" if he comes near the fence again.
- Gun Fu: Parodied when Bart leaps into the air brandishing a pair of pricing guns and uses them to tag a massive number of items while taking action poses for his wedding scam.
- Heel Realization: Gina has one when she and Bart are arrested, and told that Bart will stay in juvenile hall even longer because of her. It inspires her to confess to Lou and Eddie that she was the one behind the escape.
- Jerk with a Heart of Gold: Gina is a vicious and cruel delinquent, and is not only willing to lie to get Bart in trouble, but threaten and attack him a few times. But it turns out her anger is due to having no family. And when she learns what Bart will go through because of her, she confesses to forcing him to make a prison break.
- Late to the Realization: When they're finally unchained, Bart has no qualms about himself and Gina going their separate ways as she's convinced him that she has a very cool family and will be able to hide out with them. When he stumbles upon her sobbing by herself, he repeatedly tries to cheer her up by reminding her of her loving family, upsetting her more every time, until it finally sinks in that she was lying and doesn't have a family at all.
- Loving Bully: Gina, to Bart. She clearly shows interest in him but violently threatens him in their very first interaction and many times subsequently.
- Manipulative Bitch: Gina claims she can act all sad to make Bart take the blame for their escape. After seeing her act, Bart claims he is screwed.
- Meaningful Name: Gina's surname of Vendetti is a clear pun on "vendetta", which is Italian for "revenge", referring to her vicious and manipulative nature.
- Mistaken for Toilet: Homer mistakes a dressing room at Costington's for the bathroom.Yes Guy: Sir, other customers need to use that dressing room.Homer: Dressing room? ...Uh-oh.
- Mundane Made Awesome: The blacksmith forging the key that is used to unlock Bart and Gina's handcuffs is played out this way.
- Mythology Gag:Bart: Why did you kiss me?! Are you lookin' to do the Bartman?
- Never My Fault: Homer refuses to take any blame for his negative reinforcement (i.e., the constant strangling) having any influence on Bart's behaviour.Lisa: You're a great mom. You're always there for Bart with love and support. His acting out was caused by negative reinforcement! [they both glare at Homer]Homer: Oh, I get it. Blame the strangler!
- Noodle Incident:
- Gina was apparently imprisoned for pushing Snow White over a parapet at Disneyland. The woman apparently survived, but according to Gina, "it's not a good life".
- Cletus' collection of figurines he whittles based on things he has seen. Most are fairly normal but one of them is Poppin' Fresh with his leg caught in a bear trap.
- No-Sell: Bart tries to bribe his way out of punishment by bribing Chief Wiggum with the wedding presents at the start of the episode, but it doesn't work as Chief Wiggum only accepts cash bribes.
- Offscreen Moment of Awesome: Somehow, Chief Wiggum managed to arrest the bear that attacked him and put him in handcuffs.
- Orphan's Ordeal: Poor Gina, when Bart finds her crying and realizes she doesn't have a family.
- Papa Wolf: Homer decides to become a guard at the juvenile hall in order to try and protect Bart from being beaten up. It works, but only briefly.
- Pooping Where You Shouldn't: Implied when Homer spends quite some time sitting in a dressing room at a clothing store.Salesman: Sir, other people have to use that dressing room.
Homer: Dressing room? ...Uh-oh. - Pop-Culture Pun Episode Title: The title is a pun on the Wandering Jew.
- Premature Aggravation: Homer Simpson does this with some frequency. Oddly enough, they usually spur him to do the right thing, although it is almost always for the wrong reasons. In this episode, Homer is initially unconcerned about Bart's escaping from the juvenile hall—his emotion is ratcheted up to alarm once his mental hypothesis concludes with Bart being forced into a shotgun wedding to an alien.
- Rage Breaking Point: Bart goes through a lot in this episode, but when Gina lashes out at him again after he tries to comfort her when he finds her sobbing because of not having a family, he decides he's had enough and fights back.
- Screw the Rules, I Have Money!: When Chief Wiggum arrests Bart, Bart tries to bribe his way out with a gift but Wiggum points to his badge, which reads "Cash Bribes Only".
- Screw the Rules, I'm Doing What's Right!: After Gina confesses to her part on the escape, Wiggum decides to let Bart go despite him still having two weeks left in his sentence.
- Signs of Disrepair: In the beginning of the episodes, a hobo walks by a sign on the Costington's store saying "Downtown's Last Gasp of Class" and drunkenly bumps into it, knocking off a few letters. Bart then walks up with his family and laughs at the resulting text on the sign, which now reads "Downtown's Last Gas of ass".
- Sham Wedding: Bart arranges a fake wedding for himself and "Lotta Cooties" (there is no such a girl/woman) so he can return the gifts the invited guests will bring for store credit. He ends up getting busted and sent to juvenile hall.
- Shout-Out: One of Cletus' wood carvings depicts a Pillsbury Doughboy with distinctive markings around its eyes.
- Special Guest: Sarah Michelle Gellar as Gina.
- Take That!: When Bart and Gina are Volleying Insults, Gina calls him a "Family Guy".
- Tsundere: Gina. She constantly threatens Bart and even tries to get him to take the blame for her prison break. It's not until the end of the episode that she tells Bart why she is this way and takes the blame.
- Would Hurt a Child: Despite being law enforcement, the security guards draw shotguns at the dance to make sure the prisoners do what the warden says. And while Bart doesn't say it outright, it's implied the guards aren't any better than the prisoners when it comes to physical abuse on him.
