The book is a satirical critique of military bureaucracy and the illogical nature of war, set during World War II. The story follows a U.S. Army Air Forces B-25 bombardier stationed in Italy, who is trying to maintain his sanity while fulfilling his service requirements so that he can go home. The novel explores the absurdity of war and military life through the experiences of the protagonist, who discovers that a bureaucratic rule, the "Catch-22", makes it impossible for him to escape his dangerous situation. The more he tries to avoid his military assignments, the deeper he gets sucked into the irrational world of military rule.

The protagonist, a young stockbroker in New Orleans, is alienated, detached, and finds more reality in movies and books than in his everyday life. He searches for meaning in life, often through his relationships with his aunt and his cousin, while also dealing with existential dread and the impending reality of turning 30. This exploration of alienation and search for identity in the modern world won the National Book Award for Fiction.

"The New York Trilogy" is a collection of three detective stories that explore the nature of identity and the search for meaning. The stories are set in New York City and feature various characters, including a detective, a writer, and a professor, who are all engaged in their own personal quests. These quests often involve elements of mystery, existentialism, and introspection, and the stories are interconnected in various ways, creating a complex and thought-provoking narrative.

"Ray" is a darkly comedic and deeply moving novel about a Vietnam War veteran and former pilot who is grappling with his past and his own self-destructive tendencies. The protagonist's candid, often rambling monologues reveal his struggles with alcoholism, his failed marriages, and his complicated relationships with women, as well as his reflections on life, death, and the human condition. Set in the American South, the novel is a raw and poignant exploration of a flawed man's search for meaning and redemption.

The book is a satirical self-help guide that explores the human condition and our place in the universe through a series of thought experiments, quizzes, and essays. It delves into topics such as existentialism, semiotics, philosophy, science, and religion, all with a humorous twist. The book challenges readers to examine their lives, their beliefs, and their perceptions of reality, ultimately suggesting that we are all a little lost in the cosmos.