Star Wars: The New Jedi Order: Star by Star, by Troy Denning.
The NJO is the Star Wars franchise’s most thorough foray into gritty, grim storytelling. I appreciate it for the dramatic impact, and its little nod to how wars really work in the refusal to let the same handful of characters stay alive through every battle they ever face, but at the same time, it is a soul-wearying storyline. Galaxy-spanning turmoil, and beloved characters inflicted with intense, often personal, pain. There are little jokes and witty banter here and there–it is Star Wars, after all–but for the most part, the unprecedentedly long (nineteen books!) series is an exploration of violence, grief, and trauma. The plucky heroes do not get through this war with their pluck even remotely intact. It’s a very difficult read.