I'm bored, so here's my updated list...
Gram Parsons
Possibly my favourite country singer-songwriter ever, he's been involved with some of the best albums of all time and been partly responsible for the directions that outlaw/alternate country took.
Emmylou Harris
My favourite 'country lady' who boasts a great voice and a good know-how of how to write effective, stylistically varied country rock tunes. Wrecking Ball is a top album too.
Gene Clark
One of the main songwriters behind the classic Byrds lineup. He has this interesting, Dylanesque (very lyric-centric and folky) slant on the country style he opts for. White Light's a classic album as well.
Guy Clark
More traditional than what I usually listen to, but that approach lets the lyrics grab your attention more which, given his knack for such things, is a great thing. His grainy kinda voice gives them that much more edge as well.
Townes Van Zandt
From what I've heard of him, his style is very similar to early Cohen and John Wesley Harding-era Dylan with more of a country vibe about it. Sounds a lot like most of the modern alternate country I've heard, which is quite something seeing as his debut came out in '69.
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