After visiting a prison rodeo, Marge volunteers to teach convicts how to be artists and befriends a prisoner Jack (guest star Creator/MichaelKeaton) who has artistic potential, but is extremely manipulative. Meanwhile, Homer suffers a back injury, visits a chiropractor, and later uses a trash can to fix people's spines.
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!!Tropes:
* ArtisticLicenseGeography: Marge looks out the kitchen window and sees both the prison ''and'' the school from the same view.
* BlatantLies: Jack lies to Marge about not burning the mural. She believes him, but moments later he sets Skinner's car and Marge sees it. When Marge confronts him, he admits to having burnt the mural, but denies having set the car on fire.
* CantYouReadTheSign=/=NotHyperbole: After Homer's accident in the rodeo, Marge asks how he's doing. He replies that he can't complain...before pointing to a sign that says "No Complaining". When the doctor points out it only applies to the prisoners, Homer begins complaining about his back and his life.
* DoesThisRemindYouOfAnything: Principal Skinner's scheduling of the school's lunch menu is an obvious jab at [[http://en.wikipedia.org/wiki/Broadcast_programming#Scheduling_strategies how network executives schedule TV shows]].
* DownerEnding: For all of Marge's efforts to help reform Jack, he still goes back to prison after betraying her trust.
** It also applies to Homer's lucrative chiropractor business being sabotaged by rival doctors with him unable to do a thing about it.
* FacePalm: Marge covers her face with her hand when she sees Jack setting Skinner's car on fire.
* KarmaHoudini: Marge may have meant well, but she still lied about Jack's parole status to get him a job working around children. No comeuppance for her though, apart from being made to look like a fool for believing in Jack.
** There's also the chiropractors who destroyed Homer's trash can and forced him out of business.
* PantheraAwesome: The original mural painting for the school team Puma's Pride is a warrior woman riding a puma.
* ShoutOut:
** Chief Wiggum tells Jack that his wife Sara is nothing like the women on ''Series/SexAndTheCity''.
** Sheriff asks Jack whether maffians in prison are like [[Series/TheSopranos the Sopranos]].
* TastesLikeDiabetes: In-universe. Even Ned Flanders thinks Skinner's idea for the mural is too sweet.
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