>>739156Pic related - It's like that sinking feeling you get at the end of Cowboy Bebop, except it starts pretty early and continues all the way though.
Texhnolyze for maximum nihilistic bleakness,
Gundam Thunderbolt for "war is hell",
Hotaru no Haka (Grave of the Fireflies) for "war is hell" civilan perspective,
Infinite Ryvuis for unsupervised children being horrible people,
Now and Then, Here and There for abuse and child soldiers,
Saikano: The Last Love Song on This Little Planet,
Soko ni Iru Boku,
Plastic Memories,
Angel Beats!,
3-gatsu no Lion,
Bokurano,
Colorful (movie),
Death Parade,
Haibane Renmei,
So Ra No Wo To,
Kamisama no Inai Nichiyoubi,
Katanagatari,
Kaiba,
Saishuu Heiki Kanojo,
Madoka Magica (if you haven't seen it already),
Devilman Crybaby,
Higurashi no Naku Koro Ni,
Berserk: Golden Age Arc film trilogy,
Clannad & After Story,
Kizumonogatari film trilogy,
Flowers of Evil (the art may take some getting used too),
Paranoia Agent,
Neon Genesis Evangelion + The End of Evangelion (but you've probably already seen this one too).
Also, you might like Higurashi no Naku Koro ni:
>https://myanimelist.net/anime/934/Higurashi_no_Naku_Koro_niAs for manga, Goodnight Punpun for soul crushing depression
Also for melancholy but not overtly soul crushing:
Kaze Tachinu
Psycho-Pass
From the New World
Parasyte: The Maxim
