My favorite Neil Young record is sort of an obscure bootleg (it was released, I don’t remember the name. I had it on my OG iPod back in high school). Same with Bob Dylan... my favorite Dylan records are all on the Bootleg Series.
EDIT: Townes Van Zandt is a different beast but may also be up your alley if you aren’t already into his work.
Haven't listened to Neil Young in a while (and don't really know what out of his discography you're referring to) but remember thinking this had some Neil Young-ish sounds to it when it came out. https://youtu.be/xn65Q-VG4CQ
(Sorry, can't for the life of me remember how to embed vids. Somebody remind me please!)