your 90s choice doesn't fit at all, you fail yourself. Try "Prince" Billy-I See a Darkness.
Actually I never listened to Will Oldham. Don't think I ever heard one single song. Been plannin' to for some time though, so if I get around to it I might rescue myself. Hate to be a failure in musical taste.
Two per decade, I can't bring myself to choose just one.
00's Steven Wilson, Mikael Akerfeldt
90's Richard D. James, Thom Yorke
80's David Byrne, Adrian Belew
70's Roger Waters, Robert Fripp
60's Don Van Vliet, Art Garfunkel
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