"Pokey Mom"
"Original Air Date: 1/14/01"
The family goes to a prison rodeo and Marge discovers that a prisoner named Jack has extraordinary painting talents. Marge volunteers to teach art at the prison and later when Jack is up for parole, Marge tells the guards of how much Jack has changed. They are convinced at what she says so they release Jack into Marge's custody. Marge manages to get Jack a job painting a mural for Springfield Elementary. He ruins his chances at staying on parole though after he lights both the mural and Principal Skinner's car on fire.
Homer was also trying to get treatment for his bad back. He accidentally falls on his trashcan and bends it all out of shape, but it cures his back. He realizes that his trashcan is a miracle-worker so he decides to use it cure other people's back problems, or course for money.
Michael Keaton guest stars as Jack.
This is Episode #258 in The Simpsons series. It is also Episode #10 in Season 12.