Life Stinks (1991)

Affluent and arrogant businessman Goddard Bolt, feuding with rival Vance Crasswell over a land deal, makes a bet with Crasswell that he has the wits and street smarts to live penniless and anonymous on the rough streets of Los Angeles for thirty days. But Bolt has a rude awakening when the reality of homelessness hits him. Still, he finds a silver lining in a burgeoning romance with Molly, a former Broadway dancer who has fallen on hard times.