Townes was the man. I noticed wlbaye's list was all Texas boys. Like Townes. There is something about Texas songwriters that is uniquely outlawish. Although Jerry Jeff was actually born and raised in Oneonta New York, he is still a fave down in the lone star state.
And I second his whole list.
Guy Clark is considered the founding father of Texas singer/songwriters.
Ray Wylie Hubbard has a lake outside Dallas named after him.
Blaze Foley , was genius walking that thin line of insanity. Tragically shot to death while coming to the aid of a friend.
Slaid Cleaves is another Yankee turned Tex/Louisana boy that is doing some great work today.
More native Texans
Jimmie Dale Gilmore
Joe Ely
Robert Earl Keen
James McMurtry
Dave Carter , a lot of duets with a golden voiced Tracy Grammer. Sadly Dave is no longer with us either.
Anything with Gurf Morlix either producing or playing on will always be great.
Another yankee, Chris Smithers !!!! "Live As I'll Ever Be" is an extraordinary showcase. Doesn't have a bad album out.
Jeffrey Foucoult, a midwestwerner I belive, is also doing great work. "Ghost Repeater" is a classic.
Chris Knight has a couple of well received albums too.
But yeah, Townes was probably the best of 'em all.