It was interesting listening to Billy Bragg talk at his show last year about the influence of Jay Bennett on the Mermaid Avenue sessions. Clearly the guy was incredibly talented. His departure from Wilco is captured in I Am Trying to Break Your Heart. But despite all that, and despite the fact that he never gained much public attention again, he produced some really good music right up until his death.
The obvious first question people will ask is does this sound like Wilco, and the answer is no. But that might put some people off but in reality its a good thing - rather than try to recreate his past glories he's moved on to something different that can more easily be judged it its own right. And doing so shows a pretty rewarding album. Ironically, given the disagreements seen in I Am Trying to Break Your Heart, this is very underproduced. In the post part its Bennett playing acoustic guitar, with some minimal additional instruments (all played by Bennett too). The sound is folky and country sounding. Lyrically its bleak but never overly morbid (in some ways it reminds me of Elliott Smith). Bennett's life had some fairly tragic elements, and his death came at time when people close to him said he had finally got himself in a good place. But Bennett's legacy remains in a wealth of fantastic music, including his solo work which is likely to be overlooked in favour of his work with Wilco.
http://freemusicarchive.org/music/Jay_Bennett/Whatever_Happened_I_Apologize/
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