Reversal of Fortune (2005 film)

Reversal of Fortune is a 2005 Showtime documentary that asks the question What would a homeless person do if they were given 100,000?

The film shows Ted doing his daily dumpsterdive, collecting cans for the days food, cigarettes and beer, when he finds a briefcase amongst the rubbish. Ted stops to brush it off and opens it up slowly and finds that it is stuffed with cash. A note atop the money reads What would a homeless person do if he were given 100,000? Shocked and in tears, Ted comes to the realization that he is the recipient of a significant amount of money.Ted almost immediately buys a new bicycle, rents a motel room and takes his buddy Mike to an amusement park. The word gets out among the homeless community and Ted, who once couldnt find a girlfriend due to his poor dental hygiene, now enjoys female companionship in his motel room. As soon as Ted notifies his mother and sisters of his attainment of wealth, they begin to take his calls and his mother invites him to stay with her until he finds his own residence. The family is shown discussing how they are concerned for Teds welfare. ........

Source: Wikipedia