The career and personal life of writer Lee are at a standstill, so he divorces his bashful wife, Robin, and dives into a new job as an entertainment journalist. His assignments take him to the swankiest corners of Manhattan, but as he jumps from one lavish party to another and engages in numerous empty romances, he starts to doubt the worth of his work. Meanwhile, top TV producer Tony falls for Robin and introduces her to the world of celebrity.

Writer Harry Block draws inspiration from people he knows, and from events that happened to him, sometimes causing these people to become alienated from him as a result.

After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a psychiatrist—she's a dreadful actress. David puts up with the leading man who is a compulsive eater, the grand dame who wants her part jazzed up, and Olive's interfering hitman/bodyguard—but, eventually he must decide whether art or life is more important.

The Narrator tells us how the radio influenced his childhood in the days before TV. In the New York City of the late 1930s to the New Year's Eve 1944, this coming-of-age tale mixes the narrator's experiences with contemporary anecdotes and urban legends of the radio stars.

Roberta is a bored suburban housewife who is fascinated with a woman, Susan, she only knows about by reading messages to and from her in the personals section of the newspaper. This fascination reaches a peak when an ad with the headline "Desperately Seeking Susan" proposes a rendezvous. Roberta goes too, and in a series of events involving amnesia and mistaken identity, steps into Susan's life.

Cecilia is a waitress in New Jersey, living a dreary life during the Great Depression. Her only escape from her mundane reality is the movie theatre. After losing her job, Cecilia goes to see 'The Purple Rose of Cairo' in hopes of raising her spirits, where she watches dashing archaeologist Tom Baxter time and again.

A hapless talent manager named Danny Rose, by helping a client, gets dragged into a love triangle involving the mob. His story is told in flashback, an anecdote shared amongst a group of comedians over lunch at New York's Carnegie Deli. Rose's one-man talent agency represents countless incompetent entertainers, including a one-legged tap dancer, and one slightly talented one: washed-up lounge singer Lou Canova, whose career is on the rebound.