When a chapter of Catch-22 was first published as a novel-in-progress in 1955 Joseph Heller got several letters of encouragement from editors. Then, when the finished book was published in 1961, Orville Prescott of the New York Times described it as "a dazzling performance that will outrage nearly as many readers as it delights." Half the reviews were positive, but the other half were negative, and some were downright scathing. New York Times Book Review contributor Richard G. Stern said the novel "gasps for want of craft and sensibility," "is repetitious and monotonous," "is an emotional hodgepodge" and certainly no novel, and, finally, that it "fails " The structure was problematic for some. Acclaimed author Norman Mailer said in Esquire: "One could take out a hundred pages anywhere from middle ... and not even the author could be certain they were gone." New Yorker critic Whitney Balhett said it "doesn't even seem to have been written; instead, it gives the impression of having been shouted onto paper," and that "what remains is a debris of sour jokes." Further, the critic said Heller "wallows in his own laughter and finally drowns in it."

The last laugh was on these reviewers, however, because although the book did not win any prizes or appear on any bestseller lists, it soon became an underground hit and sold extremely well in paperback. More and more critics began to see in it what readers saw. The book had quickly become a favorite of the counterculture because of its antiauthoritanan and antiwar attitude. As Eliot Fremont-Smith said in the Village Voice (New York City's progressive counterculture newspaper), "[Catch-22] came when we still cherished nice notions about WWII. Demolishing these, it released an irreverence that had, until then, dared not speak its name." While Catch-22 was set in World War II its message was very contemporary. As some critics pointed out, in Catch-22 the real enemy is bureaucracy, and Vietnam was a war in which the real enemy seemed to be not the Viet Cong but the U.S. military and big business, which dehumanize people. Carol Pearson wrote in the CEA Critic that the book captures how people "react to meaninglessness by renouncing their humanity, becoming cogs in the machine. With no logical explanation to make suffering and death meaningful and acceptable, people renounce their power to think and retreat to a simpleminded respect for law and accepted "truth." Jean E Kennard wrote in Mosaic, "Heller's horrifying vision of service life in World War II is merely an illustration of the human condition itself."

Raymond M. Olderman wrote in Beyond the Waste Land that the key scene of the novel is when the M.P.s arrest Yossarian for being AWOL while they overlook the murdered young Italian girl lying in the street. This incident, Olderman said, symbolizes "much of the entire novel's warning—that in place of the humane we find the thunder of the marching boot, the destruction of the human, arrested by the growth of the military-economic institution." This institution is personified by Milo Minderbinder, the wheeling and dealing businessman who values money and business deals above all else. In the Canadian Review of American Studies, reviewer Mike Frank said that "for Milo, contract, and the entire economic structure and ethical system it embodies and represents, is more sacred than human life." After all, Milo even trades away the men's life rafts and makes a deal with the Germans to bomb the Americans' own base.

Critics pointed out that Yossarian's sense of powerlessness in the face of large institutions such as the military,...