Catch-22 by Joseph Heller (1961)

There is exactly one catch, and it is Catch-22: a man crazy enough to want grounding need only ask to be grounded, and the asking proves him sane enough to fly. The logic closes like a fist. Yossarian, an American bombardier on a speck of island near the war's end, has worked out that the people most determined to kill him are not the Germans but his own commanders, who keep raising the number of missions each time he nears the total that would send him home. Heller spins this single paradox outward into a whole circus, a mess officer bombing his own base under contract, a colonel in love with tidy formations, men vanishing into paperwork. And then the laughter, which has been frantic, almost cruel, turns out to have been guarding something. The novel keeps returning to a wounded gunner in the back of a plane, withholding the worst of it, until it can bear to tell you everything. You will not stop laughing, and you will not be ready.