I definitely recognize Wilco has continued to experiment and try different things, while Son Volt has pretty much stayed in the same lane. I haven't kept up to date w/ new releases from any of those bands from that era. Son Volt's A Retrospective: 1995-2000 is a pretty darn good place to start for them.
I saw Ryan Adams live once, not with any of his bands, many years ago. It was a singer/songwriter showcase. I was mostly there to see Kim Richey, I honestly can't even remember who the third artist was. They took turns doing their own songs, while the other 2 accompanied them. I was not overly impressed w/ Adams. He seemed to be extremely drunk or extremely high or both, he was barely functional. Somehow he managed to play guitar and sing, but he could hardly talk. Spent most of his time trying to relight his cigarette (gives you some idea how long ago it was, back when people smoked in bars)
On the subject of concerts, I saw the Old 97's touring for the 15 year anniversary of Too Far To Care. They did every song from the album, did a short intermission, then came back and played a bunch of their other songs. Those guys kicked butt, great show, very energetic.