Homey has a questionable criminal history which has caused severe emotional problems, specifically a lifelong grudge towards The Man. This side of him comes out whenever he leads the children in a sing-along. Much of the credit for the character goes to Paul Mooney, who was known to react "Aw no, homey!" whenever a writer pitched a sketch idea that might sound too racist. Damon became inspired, wondering "What if Paul were a clown?" -- and the rest is history.