Big-Lipped Alligator Moment: When Yossarian is recuperating from being stabbed by Nately's whore, a strange, thin man appears in front of him and says, "We've got your pal, buddy." We never find out who he is, who he's referring to, or if he was even real or an anaesthetic-induced hallucination.
"Funny Aneurysm" Moment: In the same conference where Yossarian asks "Where are the Snowdens of yesteryear?" (see Hilarious in Hindsight, below) it is preceded by a barrage of nonsensical questions, unattributed but presumably asked by soldiers who were bored and trolling. One of them was "How was trump at Munich?" In 2016, Donald Trump was running for president, and in June of that year won the Republican nomination. His acceptance speech was criticized as being full of extreme xenophobia and racism. A month later, a terrorist attack in Munich killed 10 people; Trump used this attack as proof that his harsh rhetoric was justified.
Hilarious in Hindsight: The inclusion of a character named Snowden, after Edward Snowden's leaking of the NSA's phone tap practices.
[...] and then there was Yossarian with the question that had no answer: 'Where are the Snowdens of yesteryear?' [...] Group Headquarters was alarmed, for there was no telling what people might find out once they felt free to ask whatever questions they wanted to. Colonel Cathcart sent Colonel Korn to stop it, and Colonel Korn succeeded with a rule governing the asking of questions. Colonel Korn's rule was a stroke of genius, Colonel Korn explained in his report to Colonel Cathcart. Under Colonel Korn's rule, the only people permitted to ask questions were those who never did.
Ho Yay: The first two lines of the novel: "It was love at first sight. The first time Yossarian saw the chaplain he fell madly in love with him."
Magnificent Bastard: Milo Minderbinder may be a mere mess officer, but he has connections all over the world and is—among other titles—mayor of an Italian city and imam of a Middle-Eastern country. Due to mastery of international import and export, including goods from Germany, and blatant pinching of various army supplies, even leaving stylish notes, he makes himself ludicrously rich, and becomes gradually even more of a capitalist wonder by turning his eye to private contracting with both the Allies and Axis. He eventually pulls off the amazing feat of bombing the regiment's own airfield for the Germans but easily avoids getting court-martialed due to his seemingly-unlimited funds. His only mistake is buying too much cotton from Egypt, but he takes care of that by convincing General Cathcart that the troops should be fine eating his excess cotton, provided they cover the cotton in chocolate sauce first.
Aarfy's rape and murder of Michaela, which is then ignored by the police.
Milo Minderbinder crosses it by trading the squadron's parachutes and replacing them with IOUs.
Vindicated by History: The book's anti-war and anti-bureaucratic tone was not relatable in the more conservative nature of 1961 America. It wasn't until the resistance towards The Vietnam War happened later in the decade did the subject matter begin to resonate among readers.
The Woobie: Major Major Major Major and, at some points, Yossarian. Also the Chaplain — poor worrywart.
Cult Classic: The movie, which was not well received in its day.