9. Michael Keaton
Played: Jack Crowley Episode: Pokey Mom After leaving an Apron Expo that Marge forces them to go to (and is the only person that doesn't enjoy it because there were too many aprons), the family stop off to see a prison rodeo on the way home. After Homer is kicked by a rogue bull, Marge notices a painting in the medical room which she's surprised to find was painted by a convict. On their way home, the same convict has raked leaves into a sunset scenery but the wind blows it away, showing it's ultimately a wasted effort. Marge returns to the prison to help Jack get out of jail on parole, to encourage his artistic talent and show the world the person she believes him to be. She gets him a job painting murals at the elementary school, and he creates a powerful piece featuring a scantily-clad female warrior atop a puma, incorporating the school's 'Puma Pride' motto. Principal Skinner complains that it has no place in the school, and orders him to change it: Jack does so, but everyone hates the new mural. Skinner then complains about him making such a bad mural, which causes Jack to flip. He burns down the painting, and then sets fire to Skinner's car whilst shouting "Puma Pride! Puma Pride!", before he is caught and returned to jail, disappointing Marge. Michael Keaton brings attitude and a touch of menace throughout his appearance. There are definite hints of Beetlejuice to his performance, perhaps a reason why he sounded so convincing as a mentally unhinged prisoner.