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By now you're surely well aware of Jay Bennett's new lawsuit against Jeff Tweedy; Jim DeRogatis has a sad update. It's just depressing - Bennett's contributions are key to my two favorite albums, Summerteeth and Yankee Hotel Foxtrot, although the brilliance of the latter has a lot to do with the shift in non-Tweedy creative influence from Bennett to Glenn Kotche. As Bob Mehr points out in his outstanding 2004 profile for the Reader: "Brought in to replace Ken Coomer during the making of Yankee Hotel Foxtrot, Kotche has become the most important catalyst for Tweedy's music since Jay Bennett." I caught Wilco live after YHF; Kotche is a sui generis rock drummer, and listening to him was my favorite part of the show; that album really captures them in a fascinating moment of creative transition. Greg Kot's biography is a fine source on that and many other things.
In 2004, Mehr also profiled Jay Bennett on his life after Wilco. Finances, for all but the most successful of musicians, are a difficult subject.
Also fascinating re Wilco and lawsuits is the one filed by Akin Fernandez of the London-based Irdial label. Fernandez released the chilling, amazing Conet Project, a collection of shortwave spy-station recordings (in and of itself a fascinating subject), from which Wilco borrowed; the title of Yankee Hotel Foxtrot comes from a Conet sample. Anyway, you'd think that spy-station broadcasts would be as public domain as any broadcast in the world, but British copyright is more restrictive, and the result, insofar as one can have such a thing, is my favorite lawsuit ever.
Update: Chicagoist has the filing.