After visiting a prison rodeo, Marge volunteers to teach convicts how to be artists and befriends a prisoner Jack (guest star Michael Keaton) 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.
- Affably Evil: 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.
- Artistic License – Geography: Marge looks out the kitchen window and sees both the prison and the school from the same view.
- Blatant Lies: 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.
- Can't You Read the Sign?/Not Hyperbole: 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.
- Does This Remind You of Anything?: Principal Skinner's scheduling of the school's lunch menu is an obvious jab at how network executives schedule TV shows.
- Downer Ending:
- 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 Chinatown.
- Face Palm: Marge covers her face with her hand when she sees Jack setting Skinner's car on fire.
- Karma Houdini: 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.
- Never My Fault: 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).
- Panthera Awesome: The original mural painting for the school team Puma's Pride is a warrior woman riding a puma.
- Tastes Like Diabetes: In-universe. Even Ned Flanders thinks Skinner's idea for the mural is too sweet.