Marge awakens Homer and reminds him of his promise to take her to the Apron Expo. While driving back from the event, Homer notices a sign announcing a prison rodeo. Intrigued, Homer heads for the rodeo grounds, where the family watches as inmates ride bucking broncos and rope calves. The event also includes bull riding, and when inmate Jack Crowley is tossed off a Brahma, the animal turns, paws the ground and prepares to charge. Homer attempts to distract the beast, but ends up being kicked into a guard tower. A sleeping guard awakens and fires tear gas into the crowd, causing spectators to scatter. Homer is placed in the prison infirmary, where he complains of agonizing back pain. Marge attempts to divert his mind by pointing to a painting of Jimi Hendrix playing a flaming guitar. When Marge realizes Jack Crowley is the artist, she reacts with surprise, as Jack is clearly talented.

Marge arranges to teach an art class at the prison, giving her a chance to befriend Jack. Despite Jack’s own admission that he is still filled with anger, Marge vouches for him at his parole board review. The warden orders Jack’s parole…and releases him into Marge’s custody. Meanwhile, Dr.Hibbert recommends that Homer seek out a chiropractor for his bad back. Homer meets with Dr.Steve, and though his technique helps the back somewhat, Homer balks at returning three times a week for many years to come. While raking up leaves, Homer staggers into a trash can and falls. The can somehow unkinks Homer’s back, and the pain vanishes. Homer decides to patent the old can, the unique dents of which perfectly match the contours of the human spine. He dubs it the “Spine-O-Cylinder.” Word of the miraculous device reaches Dr.Steve, who threatens to stop Homer unless he gives up his business. Meanwhile, Marge arranges for Jack to paint a mural at Springfield Elementary. She gets him the job by telling Principal Skinner that he attended Waterville State, a small liberal arts college (in reality, Jack spent six years in Waterville State prison).

Jack’s mural features a Frank Frazetta-esque female warrior astride a snarling puma. Skinner is horrified at the sight, then pulls out his original sketch, which features a cuddly puma and a little girl and boy. Jack agrees to change the art and make it look more like Skinner’s original concept. But deep down, Jack resents Skinner’s meddling. Meanwhile, two suited chiropractors steal Homer’s beloved invention and mangled it. Homer vows revenge, but Moe encourages him to forget about it. Later, Skinner unveils Jack’s revised mural, which features a cloying version of Skinner’s concept sketch. The crowd is unimpressed. Later, a deeply angered Jack sets fire to the mural, destroying it. When Jack claims he is innocent, Marge again helps him. But a short time later, Jack pours gasoline on Skinner ’s car and sets it ablaze. He again professes his innocence, but this time, Marge catches him in the act. Chief Wiggum hauls Jack away…to the bus station.