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.
* AffablyEvil: Jack's a convict with a history of violence and fierce temper. He's also very friendly when he's mellow, appreciates all that Marge does for him, and Apu even claims he was polite after Jack shot him.
* 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 on fire and Marge sees it. When Marge confronts him, he admits to having burnt the mural, but denies having set the car on fire.
* TheBore: More evidence that Skinner aims to take anything fun out of being in school because he has no idea of what interests kids--he gets on Jack's case because he dislikes the original (that has both PantheraAwesome and BrawnHilda, and makes everybody else who sees it feel ecstatic) and he says it's because it's "too exciting and improper" for a school (his own suggestion definitely would fit better on a kindergarden, if one feels generous), he switches food around in the weekly lunch plan because he thinks kids are getting too excited when they get it on Thursdays ''and'' he completely kills a joke about the Superintendent on the unveiling because he says it wrongly and tries to recover by explaining it.
* BrickJoke: When Marge is baking a cake for the warden in an attempt to help Jack get parole, she agrees to let Bart have a piece, but only if he finishes his ice cream, which he struggles to do. Later, when she's making cupcakes for Skinner in order to bribe him into letting Jack paint the mural, she gives one to Jack, but only if he finishes his ice cream, which he struggles to do.
* TheCameo: Sideshow Bob is seen in the prison infirmary with his face and hair all wrapped up in bandages.
* 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.
* DisproportionateRetribution: After Skinner made him both change the original mural and blamed him for the failure of the new one, Jack set fire to the school.
* 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. His plot even references the downer ending of ''Film/{{Chinatown}}''.
* EveryoneHasStandards: Ned Flanders is, simply speaking, one of the strongest examples of MoralGuardians on the show, and a man who has enforced morally wholesome and "safe" entertainment on his children to the point that other people think [[AmbiguouslyGay there's something wrong with them]]. Even ''he'' thinks that the mural's design is TastesLikeDiabetes overkill.
* FacePalm: Marge covers her face with her hand when she sees Jack setting Skinner's car on fire.
* {{Foreshadowing}}: After her first day working at the prison, Marge tells Bart that Sideshow Bob sends his regards and that [[Recap/TheSimpsonsS12E13DayOfTheJackanapes he's looking forward to seeing Bart real soon]].
* {{Hypocrite}}: Skinner. On top of everything else he does during the episode that he refuses to take any faults about, he casually mentions that Jack's attempt to burn the school would have failed ''because it's full of asbestos''.
* InstantlyProvenWrong: Jack assures Marge that he wasn't the one that set the mural on fire (and he's convincing enough that Marge tries to buy him time to run away--and at the time the audience may also believe him). The ten seconds she bought him were all that he needed for him to set ''Skinner's car'' on fire ([[ImplausibleDeniability and then say that it isn't his fault]]).
* {{Irony}}:
-->'''Dr. Steve:''' Simpson! You're not a licensed chiropractor, and you're stealing patients from me and from Dr. Steffi.\\
'''Homer:''' Boy, talk about irony. The AMA tries to drive you guys out of business, now you're doing the same to me. Think about the irony.\\
'''Dr. Steve:''' ''[grabbing Homer by the collar]'' You've been warned. Stop chiropracting.\\
'''Homer:''' ''[choking]'' [[SkewedPriorities Not unless you think about the irony.]]
* 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.
* MythologyGag: Homer asks Bart what happened to his blue shirt, to which Bart replies that he's never worn one. While Bart hasn't worn one on the show, several pieces of merchandise including posters, cards, comics, and toys have featured him wearing one.
* NeverMyFault: When the overly cutesy school mural is met with an overwhelmingly negative reception, Skinner pins the blame entirely on Jack, even though he was the one who forced Jack to paint it in the first place (and over the more heroic-looking mural he made first). He also puts the blame on his botched joke on the unveiling act on the writer (the writer, that is on the crowd and is a professional, just says that a better comedian would have salvaged it).
* PantheraAwesome: The original mural painting for the school team Puma's Pride is a warrior woman riding a puma.
* ShoutOut:
** The title, while not having any material from the source, it's referring to ''Franchise/{{Pokemon}}''.
** 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]].
** After the chiropractors destroy Homer's back-fixing garbage can, Moe sadly tells him: "[[Film/{{Chinatown}} Forget it, Homer. It's Chiro-town.]]"
* ShownTheirWork: When Dr. Hibbert, unable to do anything about Homer's back injury, gives him a chiropractor's phone number, Homer brings up the fact that medical doctors oppose chiropractors. Dr. Hibbert admits that's their official position but he actually believes chiropractors do a good work.
* TastesLikeDiabetes: In-universe. Even Ned Flanders thinks Skinner's idea for the mural is too sweet.