Hm. Tough to narrow it down to songs as I'm more fixated on sort of the complete picture, but here would be some I dig. It was also a matter of some of this stuff hitting me at just the right time in life.
Grubbs in particular was super meaningful. We both were punk kids trapped at the same private school in different times. Hearing stories of Squirrel Bait playing talent shows a decade before I was playing weird rock music at talent shows meant a lot. His later bands like Gastr del Sol were a gateway to so much along with the labels he and O'Rourke curated for Drag City as I approached graduation.
Bonus suggestions. Jeff and Jason from Rodan/Shipping News/June of 44:
Being a punk rock kid growing up in Louisville surrounded by brilliance shaped who I am. I'll stop making suggestions of good Louisville guitar punk because it's endless