The Wandering Juvie

When the Simpson family is at the Costington's department store, Bart uses the wedding gift registry as a prank to register himself and his bride, "Lotta Cooties", for wedding presents. Bart invites many people to his so-called "wedding" and plans to take all the unused gifts back for store credit, but he is stopped in his tracks by Chief Wiggum, who arrests Bart. Bart tries to bribe Chief Wiggum with the wedding presents, but Chief Wiggum only accepts cash bribes, as stated on his badge. Bart is sentenced to six months of juvenile detention by Judge Constance Harm, going to a detention center.

Guest star Sarah Michelle Gellar provides the voice for Gina Vendetti.

At the detention center, Bart is being harassed by Gina Vendetti amongst others (she threatens to make his puberty very boring whilst wielding a penknife) when he encounters Homer, who has taken the job of being a prison guard to protect him. Unfortunately, his shift ends until two weeks from that day. He has another problem when he is partnered with Gina Vendetti for the "Prom". When they are dancing, Gina thinks of a way she can escape. But due to the fact that they are handcuffed together, she automatically brings Bart along. Slowly, they gain each other's trust and then kiss. They are on the lam and look for a blacksmith who can remove their cuffs. They are freed, but after it happens, Gina is alone and forlorn. Gina yells at Bart and Bart calls her a psycho. They engage in a brutal fight and this time, Bart is so angry he actually wants to kill her as much as she wants to kill him. The police come and arrest them, telling the Simpsons that now Bart will be in Juvie even longer. Gina, feeling terrible, confesses she does not have a family when she returns to jail (also clearing Bart of all charges that would result in him remaining in prison), but the Simpsons and the prison warden step in to help Gina by offering a Mexican food feast in her cell at the end.

[edit] Cultural references

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Abercrombie & Fitch and others — The "Little Hooker" T-shirt line sold at Costington's is a spoof of clothing manufacturers marketing adult fashions toward a pre-teen (especially female) demographic.
Battle of Waterloo — The Itchy & Scratchy short, "The Battle of Slaughter-loo," is a play on Napoleon Bonaparte's last battle in 1815.
The Defiant Ones — Much of this episode's plot (where a shackled-together Bart and Gina escape prison and learn to work together to survive) is inspired from the 1958 movie starring Tony Curtis and Sidney Poitier.
Family Guy — Gina's insult directed at Bart is a reference to the animated TV series which also airs on Fox and focuses on a dysfunctional family, furthering the supposed rivalry between Matt Groening and Seth Macfarlane (who is a fan of The Simpsons, according to the DVD commentary of the season four episode "PTV")
It's a Small World and Snow White and the Seven Dwarfs — In another nod to Disney, Gina's picture (depicting her pushing Snow White off a high wall, beneath which is the caption "It's a fall world") refers to the ride at Walt Disney theme parks, and the title character of the children's novel and 1937 animated feature.
Let's Make a Deal — Skinner makes a remark about his mother winning dishes on the long-running game show, on which dinnerware was one of the staple prizes.
Pillsbury Doughboy — Cletus' wood carving resembles the advertising icon. The markings around the carving's eyes, however, suggest that it may actually be one of the evil doughboys from Johnny the Homicidal Maniac.
Punch and Judy — Chief Wiggum's remark, "Well, well, if it isn't Punch and Juvie," is a play on the name of a puppet show dating from the 1600s.
"The Seven Habits of Highly Effective People" — "The Ten Habits of Highly Effective Criminals," Snake's self-help book targeted at criminals, is inspired by the 1989 self-help book by Stephen R. Covey.
The Shawshank Redemption — The sign in the warden's office — "HIS JUDGEMENT COMETH AND THAT RIGHT SOON" — is the same as the one seen in Warden Norton's office in the 1994 movie.
Television editing — The heavily edited Itchy & Scratchy short is reminiscent of classic cartoons (e.g., Looney Tunes and Merrie Melodies) being edited on television due to issues of violence, racial stereotypes, and subject matter deemed inappropriate for children.
Wandering Jew — The episode title is a play on the name of a figure from medieval Christian folklore.