Catch-22 was a dark and comedic novel that turned from “Oh no this’ll be some funny war story” but as you get to the middle you realize how horrific the situations become, and you start pitying the characters and hating some, and later learn they die horribly, some suicide some being mutilated by plane engines or drowning or being thrown from windows.

: https://www.amazon.com/Catch-22-50th-Anniversary-Joseph-Heller/dp/1451626657