Goodnight Punpun and No Longer Human made me cry hard, so much so I had to take breaks from reading them.
I want to read Metamorphosis so bad...
Tuesdays with Morrie by Mitch Albom
I think this book made me cry mostly because Morrie suffered from ALS, and I experienced my grandfather suffer from MND. It's a bittersweet book regardless of the connection I have with it, and I thoroughly enjoyed my time spent with Morrie through the book. Highly recommend for a good read and some old man life lessons <3!
The first book that came to mind is The Road by Cormac McCarthy. Gut wrenchingly, heart wrenchingly sad. After finishing it I cried & then stared at a wall for like fifteen minutes. I still think about it pretty regularly. Thinking about it is actually making me tear up lol
I'd say Turtles All The Way Down by John Green. The book is mostly about a teenage girl dealing with a murder mystery in her town and her fairly severe OCD, and John Green mostly writes the OCD stuff from his own experience with it. As someone who has pretty significant clinical anxiety issues and intrusive thoughts, the book was pretty spot on in terms of the daily internal monologue of all that. What really got to me was how the protagonist's family and friends reacted to her anxieties, with a lot of them not really fully understanding the scope of her issues and trying to be sympathetic while seeing the main character as irrational and a little eccentric for her mental state. That was very well written overall, but it hit a little too close to home tbh. Though to be fair the only John Green book that didn't make me cry was Paper Towns. Between Looking For Alaska and The Fault In Our Stars that man has made me run through more tissues than I care to think about with his writing.
For me in high school, it was Defending Jacob that got me. It was the first book I read that dared not to have a happy ending, and it changed my view on stories and storytelling. Recently, though, the book that made me cry was the short story There Will Come Soft Rains. Didn't help that there was a lovingly animated Soviet version made in '84.
A couple have, such as Aurora by Kim Stanley Robinson. I have no clue why it caused me to cry, but the ending of it was just so touching. Blue Mars also by Kim Stanley Robinson sorta made me cry, not because of it's ending or anything like that (even though its ending was great), but because I was sad that I had finished the Mars Trilogy, and there were no books after that. It was such a good series, and leaving it doesn't feel good or right. It got to its end, but its still hard to accept. The first one that came to my mind however, has gotta be A Happy Death by Camus. It's just such a, well sweet isn't the right word, but bittersweet, feeling-packed book. It's so eloquently written that to properly analyze the whole thing, you would need something well over the length of the book itself. Each sentence of story begets two of beauty.
the first book that comes to mind is earthlings by sayaka murata. that book is utterly devastating, like it reaches right into your heart and just digs its nails in. and it doesn't do this because it wants to hurt you, it does this because it desperately wants to connect. it's an incredible novel! but pretty damn triggering, so watch out.
other books that make me feel that way are honestly anything that banana yoshimoto has written. we've only read kitchen and lizard, and both of those books feel like your soul is being opened up and that a present is being placed inside, and then it's all gently being stitched back up. it's a lot kinder than earthlings, but it makes you cry from the honesty and earnestness and sheer kindness of the text.
needless to say, i would really recommend both murata's and yoshimoto's works.
Stone Butch Blues by Leslie Feinberg is a book that made me cry multiple times, especially in the latter parts. The protagonist, Jess, repeatedly has to start over after losing her home, her livelihood and her friends multiple times. The book covers very heavy subject matter, but what stings the most is when even in periods of relative peace and stability we are constantly reminded that there is no real security for the oppressed, that Jess' life will be precarious despite the apparent peace. It emphasizes the ephemerality of safety for those in poverty.
Despite all this, Jess starts over. She meets new people and makes peace with her past. In the haze of discrimination and hate, the joyful points of Jess' life serve as beacons of hope, both for her, who tries to hold on to mementos and make peace with old friends, and for the reader who gets to appreciate these havens of happiness.