New York City in the 50s is seen as a hotbed of new artistic expression, free love, drinking, jazz, radical politics and psychoanalysis. The documentary follows writer Dan Wakefield as his restless rebellion forces him to leave his middle-class, conformist life in Indianapolis. He escapes to New York where he dreams of writing a novel, falls in love, questions the meaning of life through psychoanalysis and meets a group of like-minded souls. Interviews with writers, actors, musicians, artists and poets fill out the picture of the city and the era.