Shep, Have U Gone Bald Inside Your Head? (Vanguard 1969)
Got this record a few years ago in a stack my aunt handed over to me (thanks!), it was sealed and I wasn't confident it would be any good so for a while I just bugged out over the cover and figured I'd sell it later. Then I ran across it in the stacks at Academy in Williamsburg with a real-money pricetag -- not in the dollar bin -- so I decided to crack it open. Pretty nice! Especially the opening track, "Good Bill's Street," with its weird organ shuffle matched w/ plaintive vocals. Couple other tracks have some gentle pop-psych touches like sitars ... but most of it is along the lines of "The Cowboy," guitar-based folk with oddball, almost Shel Silverstein lyrics.

Shep - "Good Bill's Street"

Shep - "The Cowboy"