Lots of music by David Sylvian. He's my favorite musician and I've found so much comfort in his work for so many years. He makes very mature contemplative, introspective, emotionally honest music that has a calm and melancholic tone. Very special to me. Probably some Prefab Sprout as well, though they are not depressive by any means, they just make my brain feel satisfied. Deacon Blues by Steely Dan for sure. The song Trepanated Earth by Ariel Pink has been stuck in my mind as something I'll play before I go for at least a decade at this point. It has a really special almost apocalyptic atmosphere, but isn't aggressive. It feels moreso like accepting ruin. As well, definitely a lot of black metal because it's just too fitting.