This playlist accompanies the Fine Tuning Podcast episode featuring James McMurtry, which I humbly suggest you check out. McMurtry's music is dark, but the despair is softened (a little) by a cheeky stridency, and the music is a top-shelf mixture of Americana, rock and folk.
The Fine Tuning Podcast is available exclusively on Spotify here.
The James McMurtry Playlist is available here.