Townes Van Zandt. Where do I start with this guy? As far as the traditional singer-songwriters go, there is no other American songwriter on his level. He's my Bob Dylan. Poet and troubadour extraordinaire, he was ravaged by alcoholism and manic depression that lent his songs a very rare quality - you feel like this is a guy who has lived each and every song he has written. He passed away due to heart failure on new year's day, 1997. This is his famous live album from 1977, which has the benefit of having a more intimate sound with just Townes and his guitar (as opposed to his albums, which are all great but have the effect of extensive overdub work which drowns out Townes' from time to time).
A top tier sampler of Townes' work:
now i'm out of prison
i got me a friend at last
and he don't cheat or steal or drink or lie
his name's codeine
and he's the nicest thing i've seen
together we're gonna wait 'round and die
waitin' around to die
