“Catch-22” follows Yossarian, a WWII bombardier whose men must keep flying more and more dangerous bombing missions. Yet if Yossarian tries to excuse himself from the deadly missions he’s assigned, he’ll be in violation of Catch-22:

A man is considered insane if he willingly continues to fly dangerous combat missions, but if he makes a formal request to be removed from duty, he is proven sane and therefore ineligible to be relieved.

What starts as a comedy slowly turns into a nightmarish tragedy as the war becomes increasingly real throughout the novel.

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Submitted by Reddit user Gyjf.