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Catch-22

Captain John Yossarian, a U.S. Army Air Force B-25 bombardier, is stationed on the Mediterranean base on Pianosa during World War II. Along with his squadron members, Yossarian is committed to flying dangerous missions, but after watching friends die, he seeks a means of escape.

While most bomber crews are rotated out after 25 missions, Yossarian's commanding officer, Colonel Cathcart, keeps raising the minimum number of missions for this base before anyone can reach it, eventually to an unobtainable 80 missions, a figure resulting from Cathcart's craving for publicity, primarily a mention in the nationally syndicated Saturday Evening Post magazine.

Futilely appealing to Cathcart, Yossarian learns that even a mental breakdown is no release when Doc Daneeka explains the "Catch-22" the Army Air Force employs:

An airman would have to be crazy to fly more missions, and if he were crazy, he would be unfit to fly.Yet, if an airman were to refuse to fly more missions, this would indicate that he is sane, which would mean that he would be fit to fly the missions. The airman is thus in an impossible "damned if you do, damned if you don't" situation.

Yossarian is haunted, in several recurring flashbacks during the film, by the bloody death of Snowden, the young turret gunner on his B-25. After Snowden's death, Yossarian temporarily refuses to wear his uniform, which Snowden bled on. He shows up at a medal ceremony naked, and later morosely sits naked in a tree, where he is visited by Lieutenant Milo Minderbinder, who rapidly progresses from squadron supply officer to a capitalistic tycoon involved in black-market money-making schemes. The bomber squadron is populated by many other comically strange characters. Major Major, the squadron's operations officer, is promoted to a squadron commander without ever having flown in a plane and refuses to see anyone in his office while he is in, instructing Sergeant Towser that people can see him when he's out. The person has to wait in the waiting room until Major Major is gone, then can go right in.

Trapped by this convoluted logic, Yossarian watches as individuals in the squadron resort to unusual means to cope; Milo concocts elaborate black market schemes while crazed Captain "Aarfy" Aardvark commits murder to silence a woman he has raped. Lieutenant Nately falls for a sex worker, Major Danby delivers goofy pep talks before every bomb run, and Captain Orr keeps crashing at sea. Meanwhile, Nurse Duckett occasionally beds Yossarian.

Nately dies as a result of an agreement between Milo and the Germans, trading surplus cotton in exchange for the squadron bombing its own base. While on a pass, Yossarian shares this news with Nately's romantic partner, who then tries to kill him.

Because of Yossarian's constant complaints, Cathcart and Lieutenant Colonel Korn eventually agree to send him home, promising him a promotion to major and awarding him a medal for the fictitious saving of Cathcart's life; the only requirement being that Yossarian agrees to "like" the colonels and praise them when he gets home.

Immediately after agreeing to Cathcart's and Korn's plan, Yossarian survives an attempt on his life when stabbed by Nately's partner, who had disguised herself as a janitor. Once recovered, Yossarian learns from Danby and Chaplain Tappman that Orr's supposed death was a hoax and that Orr's repeated "crash" landings had been a subterfuge for practicing and planning his own escape from the madness. Yossarian is informed that Orr ditched the plane and paddled a rescue raft all the way to Sweden on his last run.

Yossarian decides to abandon the deal with Cathcart, leaps out of the hospital window, takes a raft from a damaged plane and, while a marching band practices for the ceremony to award Yossarian the promotion and medal, he hops into the sea, climbs into the raft and starts paddling.