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Tear Jerker: Catch-22
The latter parts of Catch-22. A story that had been lighthearted and bizarre suddenly takes a turn for dark territory, killing off a lot of the characters, and the second-to-last chapter that details Snowden's death.
Yossarian's memories of the dying Snowden. "I'm cold."
After Orr is shot down over the ocean, Yossarian reassures himself that Orr will manage to survive and make it back, like so many times before. He then waits in his tent for Orr to return, for a long time, telling himself that Orr is going to come back aaany minute now...
The chaplain breaking down in tears, when he learns Nately has been killed.
The part where the completely bandaged Yossarian has to pretend to be a dying soldier named Giuseppe in front of Giuseppe's parents (the real Giuseppe having died recently, and the hospital staff not wanting to disappoint them). Sure, it's pretty funny, but it's also kinda sad.
What's worse is the implication that, unlike Giuseppe's father and brother, his mother knows perfectly well that it is not her son in the ward and that he has already died.
The father: When you talk to the man upstairs, I want you to tell Him something for me. Tell Him it ain't right for people to die while they're young. I mean it. Tell Him if they got to die at all, they got to die when they're old. I want you to tell Him that. I don't think He knows it ain't right, because He's supposed to be good and it's been going on for a long, long time. Okay?
The brother: And don't let anyone up there push you around. You'll be just as good as anyone else in Heaven, even though you are Italian.
"Dress warm," said the mother, who seemed to know.
Also, the deaths of McWatt and Kid Sampson, McWatt especially. Arrgh. McWatt accidentally slices Kid Sampson in two while flying low in his plane for fun, and when he realizes what he had done he has the entire crew jump out on parachutes, then flies into a mountain.