Suggest one obsure album we all should hear

Heatmiser - Mic City Sons (Eliot Smith's former band)

Vulgar Boatmen - You and Your Sister (pure low-key R&R pleasure)

A Man Called E  (Eels frontman - prior to)

+1 on Bruce Cockburn: I like "High Winds, White Sky : 1971 : early, happy, trippy, folky

Obscure

Ann Richards & Stan Kenton : Two Much : 1961 : slowburn jazz vocals

Sea Level : (self titled ) 1977 : smooth and funky jazz fusion, a great lineup.

Sea Level: One the Edge : 1978 : funky and musical jazz fusion, wow!

The Beau Brummels : Bradley’s Barn : 1968: early San Fran folk Rock

Ron Elliott: The Candelstickmalker : 1969 : only sole effort of Beau Brummels member : Dark and musical

Poi Dog Pondering : Pomegranite : 1995 : sonically interesting and intense release from the Austin-based musical "family’ that featured Frank Orall

Billy Price and Otis Clay "This time for real"

Firesign Theater
"How Can You Be In Two Places at Once When You're Not Anywhere At All?"

Not really sure if this qualifies as obscure. Perhaps less known and certainly underappreciated. One of the finest voices ever.

"Greetings From LA" Tim Buckley 
Unfortunately, there is no video from this album, but I did find this gem from his album "Sefronia".

https://youtu.be/LtU-9EMSYu0