Chris Smither, yes, very good stuff. I also think it's Mads Vinding in the photo above. Side profile looks like him, not Mikkelborg.
And I agree, was lucky to be in the right time and place (teenager into early 20s) for the 90s independent rock scene/college radio which led me to people like William Parker, Matt Shipp, David S. Ware, and many others. All of that stuff was defining to me.