- “Puma pride! Puma pride! Catch the fever, Skinner!”
- ―Jack Crowley, while burning Skinner's car
Jack Crowley is a criminal that was imprisoned in the Waterville State Prison for shooting Apu. Marge later learns that he was imprisoned at least one other time for an incident involving a young couple and a tractor. He participated in the prison rodeo where Homer injured his back.
Although he is a convict, Crowley is a skilled artist first noticed by Marge for his painting of Jimi Hendrix (which was painted with pudding) and a sunset with raked leaves. Crowley was later employed to paint a mural for the Springfield Elementary School. Principal Skinner had Crowley change his mural from an edgier style to a more childish and colorful image that everyone hates during the reveal, Skinner immediately passed the blame off to Jack while not accepting his share in the blame. Enraged, Crowley burns the mural, and later, Skinner's car. He is last seen going back to jail.
He also revealed that he was Jewish.
Relationship with other characters
Crowley is seen by Marge to be a gifted artist and a troubled, but nice person. Marge trusts him unconditionally at first, but later sees that he is bad person when he burns the mural and car.
Skinner and Crowley's relationship is rocky from the start. Skinner talks down to Crowley, calling him "college boy." Skinner sends Crowley over the edge after criticizing Crowley for the mural that Skinner drew on the napkin.