In the late '40s stand-up comic Lenny Bruce shared the stage with the local strippers, and married one of them. By the '50s he had perfected a jazzy, improvisational delivery that led to TV dates with hosts Steve Allen and Hugh Hefner. By the early '60s Bruce's sold out club dates were cracking up audiences from coast to coast, taking a hipster's aim at conventionality and hypocrisy (and the Catholic Church) arguably the reason prosecutors now felt compelled to arrest him repeatedly for obscenity and narcotics possession. The film revisits Lenny Bruce's greatest triumphs and the depths of his tragedy.