His best-known work is the 1961 novel Catch-22, a satire on war and bureaucracy, whose title has become a synonym for an absurd or contradictory choice.

[5][6] Even as a child, he loved to write; as a teenager, he wrote a story about the Soviet invasion of Finland and sent it to the New York Daily News, which rejected it.

[7] After graduating from Abraham Lincoln High School in 1941,[8][9] Heller spent the next year working as a blacksmith's apprentice,[10] a messenger boy, and a filing clerk.

[18] Although he originally intended the story to be no longer than a novelette, Heller was able to add enough substance to the plot that he felt it could become his first novel.

[10] The finished novel describes the wartime experiences of Army Air Corps Captain John Yossarian.

Yossarian devises multiple strategies to avoid combat missions, but the military bureaucracy is always able to find a way to make him stay.

[18] In the years after its release in paperback in October 1962, however, Catch-22 caught the imaginations of many baby boomers, who identified with the novel's anti-war sentiments.

[10] The United States Air Force Academy uses the novel to "help prospective officers recognize the dehumanizing aspects of bureaucracy.

"[citation needed] The movie rights to the novel were purchased in 1962, and, combined with his royalties, made Heller a millionaire.

The film, which was directed by Mike Nichols and starred Alan Arkin, Jon Voight and Orson Welles, was not released until 1970.

[6] In April 1998, Lewis Pollock wrote to The Sunday Times for clarification as to "the amazing similarity of characters, personality traits, eccentricities, physical descriptions, personnel injuries and incidents" in Catch-22 and a novel published in England in 1951.

The book that spawned the request was written by Louis Falstein and titled The Sky Is a Lonely Place in Britain and Face of a Hero in the United States.

The Times stated: "Both have central characters who are using their wits to escape the aerial carnage; both are haunted by an omnipresent injured airman, invisible inside a white body cast".

Critics were enthusiastic about the book, and both its hardcover and paperback editions reached number one on the New York Times bestseller list.

[19] He was admitted to the Intensive Care Unit of Mount Sinai Medical Hospital the same day,[29] and remained there, bedridden, until his condition had improved enough to permit his transfer to the Rusk Institute of Rehabilitation Medicine on January 26, 1982.

[30] His illness and recovery are recounted at great length in the autobiographical No Laughing Matter,[31] which contains alternating chapters by Heller and his good friend Speed Vogel.

The book describes the assistance and companionship Heller received during this period from a number of his prominent friends—Mel Brooks, Mario Puzo, Dustin Hoffman and George Mandel among them.

[32] He died of a heart attack at his home in East Hampton, on Long Island, in December 1999,[10][25] shortly after the completion of his final novel, Portrait of an Artist, as an Old Man.