In my opinion, most Mountain Goats songs. John Darnielle is an amazing songwriter, and he tackles very difficult subjects, especially in his earlier stuff. The Sunset Tree album is all about growing up with an abusive step-father, Tallahassee about a couple who fall apart, Full Force Galesburg about a small town you can disappear in, etc. Some of my favorites include “The Mess Inside” about two people that can’t find the love they lost, “No Children” about a couple that hate each other, and “Jeff Davis County Blues” about a sort of meditative experience after a breakup. I’d give it all a listen. To go even deeper, the albums All Hail West Texas and In League With Dragons have sort of companion podcast seasons (I Only Listen To The Mountain Goats) where Darnielle and Joseph Fink of Welcome to Nightvale go through each song, the inspiration, the meaning, stuff like that.

Wrong Ones by Julliette Reilly

The entire Nurture album by Porter Robinson. Deals with loss, existence, joy, AI, etc.