Good post jriggy. I read Jerry or Bob say it was CSN’s harmonizing that prompted them to start trying to sing. And I know Jerry played banjo in Folk/Bluegrass bands around Stanford University in Palo Alto (whose Frat houses my High School garage band played at in 1967-8. My introduction to the joys and danger of alcohol ;-). However, the songs and playing on Workingman’s Dead show no non-vocal CSN influence, but a lot of The Band’s. Listen to the two, back-to-back. It’s obvious. As does Neil Young’s Harvest, the only album of his that sounds as it does. Have you carefully watched Neil’s face and body language as he is brought up on stage at The Last Waltz? And what he says about The Band at that moment? Look for the "white substance" in his nostrils---he’s loaded to the gills!
As to my opinion of The Dead’s singing.....I thought Pig Pen’s vocals fit their music pretty well when I saw them live in The Panhandle at Golden Gate Park in the Summer of ’67 (top THAT ;-). He did most the singing, though I think Jerry sings on "The Golden Road (To Unlimited Devotion)", a cool song. They were a VERY different band on their 1967 debut album, almost proto-punk in a way. They moved into extended jamming on their 1968 2nd and 1969 3rd albums, the one’s of theirs’ I actually kinda like. So I was not prepared for Workingman’s Dead in 1970. You know they toured across Canada in 1970 with The Band (as documented in the documentary Festival Express) and others, right? Coincidence?
Back to Jerry and Bob’s singing. We’ll have to agree to disagree. I played and recorded with a songwriter who had perfect pitch, and I’m afraid he drilled harmony and counterpoint singing into my brain. I can’t STAND even slightly flat singing, and their singing is far more than slightly flat. It’s just SO sour. You can’t hear that? As for soul, sorry mate, my standards are pretty high in that regard. Ray Charles, Solomon Burke, Big Joe Turner, Wilson Pickett, and, yes, The Band’s Richard Manuel sing soulfully. Jerry and Bob sound like boys to me, not men. They are constantly straining to reach notes, and lots of words are sung as if they are running out of breath. They are simply not very talented singers.