A white family has had the same Black maid for many years. When she tells them she wants to go back to school and will be leaving soon, the 20ish year old son decides what she needs is a change and begins searching for a man to wine and dine her, but who won't marry her, thinking that this will distract her from her plans. The man he finds doesn't entirely cooperate.

The outrageous, groundbreaking comic Lenny Bruce, whose iconoclastic material in a conservative era got him into tragic trouble, is profiled by a close friend, Fred Baker, who prefers to remember the laughs Lenny Bruce's memory evokes instead of the tears. By presenting Bruce's landmark skits on the Steve Allen Show, his failed TV pilot episode and a candid interview with Nat Hentoff, Bruce's genius and anguish show through the dramatic and tragic trajectory of his career from aspiring artist to hunted "lawbreaker".