In his extravagant office, ruthless businessman Goddard Bolt holds a meeting with his attorneys. As one lawyer, Pritchard, describes complications arising from business interests in South America and Ft. Lauderdale, Florida, Goddard acts completely disinterested. Goddard is preoccupied with his scale-model of two and a half square miles of a dilapidated section of downtown Los Angeles, California, that he is planning to buy for over $4 billion so he can transform it into a development called Bolt Center. The meeting is interrupted by rival developer Vance Crasswell, who attempts to buy out Goddard's share of the downtown slum. When Goddard refuses to sell, Crasswell tricks him into accepting a bet challenging Goddard to live on the streets without money or credit cards for a month. Goddard agrees to sell his share of the land to Crasswell if he loses the bet. When Goddard prepares by dumping his wallet and shaving his mustache, Crasswell rips off his rival's toupee to make him unrecognizable. An ankle bracelet monitor is placed on Goddard and Crasswell dumps him onto a filthy downtown street. When night falls, Goddard attempts to rent a room at a flophouse, but the manager kicks him out because he does not have any money. On the street, Goddard tries to sleep in an abandoned drainpipe in a back alley, but he is chased out by rats. The next morning, Sailor, an elderly homeless man, urinates on a flattened cardboard box, from under which Goddard pops out. Goddard spends his day trying to make money by cleaning car windshields and dancing for change. However, his efforts are fruitless. When two crooks, Mean Victor and Yo, steal Goddard's shoes off his feet, a homeless woman named Molly chases them away. After giving Goddard another pair of shoes, Molly leads him to the Mission so he can eat a decent meal. They find a table and dine with Sailor and his friend, Fumes. Afterward, Molly and Goddard walk past a bride and groom leaving a rundown chapel. While Goddard is sentimental, Molly becomes irate, because her ex-husband ruined her life and made her homeless. Returning to Molly's makeshift alley "home," she and Goddard watch all of her possessions burn after being ignited by Mean Victor and Yo. Molly convinces Goddard they need to get revenge against the men. Goddard entices the culprits to chase him to a spot where Molly, Sailor and Fumes dump a vat of boiling water on them from a fire escape above. At night, Goddard and Molly sleep in a cardboard box, but a rainstorm floods them out. They attempt to find shelter at the Mission, but Crasswell has ordered his advisors to have the building closed for the night. Sailor complains that the rain is making him feel ill, so he walks by himself to a clinic. The next morning, Goddard finds Sailor dead on the sidewalk. Elsewhere, Crasswell visits Goddard's attorneys and bribes them to betray their client. At last, when the bet is over, Goddard shares a bottle of stolen champagne with Molly. They retire to an abandoned warehouse where they dance then make love. Afterward, they go to Goddard's Beverly Hills, California, mansion where a party is in full swing. Inside, Crasswell denies knowledge of the bet while Goddard's attorneys keep silent. Crasswell then announces that Goddard has lost his entire fortune because he was assumed dead. Security guards throw Molly and Goddard out of his home. The next day, as Goddard wanders the streets and mumbles to himself about his predicament, he meets another homeless man who claims to be J. Paul Getty, the richest man in the world. As the two men get into an altercation over their respective wealth, the police break up the fight. Paramedics haul Goddard to a hospital where he is overmedicated with Thorazine. As Goddard lies unconscious in the Intensive Care Unit, Molly attempts to cheer him up by saying that she loves him. He awakens and is pleased to see her. Across town, Crasswell presides over the groundbreaking ceremony for his new downtown development. The Los Angeles elite applaud when Crasswell orders bulldozers plow over a "tent city" populated by the homeless. Released from the hospital, Goddard witnesses the demolition and grabs a bullhorn, with which he encourages the scattering transients to fight back against the developers. Although the homeless do not heed Goddard's call to action, they stop to listen to Molly who gives a rousing speech about needing to show the world how badly the rich treat the poor. Inspired, the homeless swarm over the elite party, wreaking havoc as they grab food and champagne. Goddard commandeers an excavator and knocks down Crasswell's banners and signs. Crasswell jumps into another excavator and the two men fight each other with their machines' claws. Goddard wins the duel, grabs Crasswell with his claw and dangles him high above the ground. When Crasswell continues to deny the bet, Goddard shakes him wildly in the claw's grip. Crasswell finally confesses as television news cameras capture him admitting that Goddard won their bet. Two weeks later, a female news anchor reports that Goddard plans to turn the downtown area into a no-cost housing development for the homeless, complete with a park, a free medical clinic and other services. Meanwhile, Goddard and Molly are married at the rundown chapel.