Amazing you went to school with Chris Whitley, that made me look him up:
Yeah, Chris was a great guy. He hung with a rough crowd, but got along with everyone, and was well liked. He was one of those folks who was wise beyond his years. Smoked like a chimney, even back then, which I believe is what cut his life so short. He was pretty passionate about dirt bikes too - big Bultaco fan, which is what he was riding back then (late 70's). Being a rider, I loved the line from his debut album, from, Look What Love Has Done:
Used to be when things got tight
I could bid you a well bye bye
Riding some two-wheeled sex machine
Like I don't have to try
Of all his albums, that first one, Living with the Law, remains my favorite. Love the tune, Phone Call from Leavenworth. We actually had a second celebrity in our graduating class - along with Chris there was Melissa Leo who's gone on to become a truly great actress. Also mature beyond her years, and also well-liked. This was a "progressive" public school in Bellows Falls, Vermont. I say progressive because back then they had moved into a custom made building (that still houses the school) where the classrooms have no walls (just a big open warehouse like space that is divided with movable dividers). Other than that, it was just another public high school.