This is director/star Mel Brooks in Frank Capra-land. He plays a billionaire businessman who makes a bet that he can live as a derelict for 30 days. Naturally he learns a lot more about life than from the top of his ivory tower, but the twist in the plot is that all his associates (he has no friends) double-cross him, and it seems he must remain a derelict for the rest of his life. More of a piece (and just slightly more serious) than most Brooks films, this is an entertainment where comedy often fails, but the overall bitter-sweet mood is quite successfully sustained. We should all meet bag ladies as attractive as Lesley Ann Warren, but there are more credible sections of the film, involving Brooks' friendships with down-and-outs and his running rivalry with a man who thinks he's J Paul Getty.
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