Well this is some shitty news. On the heels of the news that Jay was having health issues and was suing Jeff Tweedy for a piece of the I Am Going To Break Your Heart DVD sales, it appears that Jay Bennett has passed on.
While Wilco was a great band until Summerteeth, the band is a total nightmare at present. When Jeff booted Jay from the band (after making him look like a total douche in the film) the last piece of anything good left that band. It was notable that John Stiratt high-tailed it back to Chicago right after that staffing change, as it seemed that Wilco was rapidly morphing into the Jeff Tweedy Experience.
They really should change the name, as there is very little to associate the old Wilco with the faux-Radiohead ridiculousness they are now purveying. I've not checked, but I'm sure there is adequate documentation of Tweedy denegrating the early (good) records ala King Of Revisionist History Ryan Adams. Credit is due, though. Any band that is that boring with Glenn Kotche and Nels Cline in the band really deserves some notice. Kudos to Jeff and Tony M. I'll give them another five years before Tweedy pulls a Van Halen and has his kids backing him.
If you're of a mind to remember the man, check out Jay's site and pick up some of his back catalog with Ed Burch or Titanic Love Affair. Rarely will you hear better music.