Catch-22

Joseph Heller's 1961 satirical novel set in a WWII American bomber squadron — following Yossarian's attempts to be grounded as insane in a war where the insanity is institutional — which became the defining anti-war novel of American literature.

Created the Catch-22 paradox — the rule that you can only be grounded for insanity if you ask to be grounded, but asking proves you're sane — as the perfect encapsulation of bureaucratic double-bind logic, and embedded it in a novel that made absurdist anti-war satire into a mass-market form.