Life Stinks (1991)

Sticking to great comedy in a way no one else can, Mel Brooks plays a wealthy businessman who finds himself getting suckered into a bet with a rival business over the worst slum area of L.A. They both want to develop on it and both own half. Mel agrees to living as a homeless person in this neighborhood. If he can make it 30 days without his wallet or anything else, then the rival will sign over his half of the property. It's full of visual gags, one-liners, and even some heartwarming scenes. Mel's character learns a lot along the way.