On Memorial Day I was starting to drink my morning coffee when I heard Jay Bennett’s name mentioned on the NPR news. I knew there could only be one reason why they would be mentioning him in the first five minutes of the show.

It was sad, but not the biggest surprise. I had heard that he was the risk-taking sort, and had seen some evidence of it.

In a way, it closed out a ten-year cycle for me. I first became aware of Wilco around 1999 when Summerteeth came out. It was a couple years after I had moved to Chicago, and although Wilco hadn’t registered with me earlier, when you live in Chicago you tend to become much more aware of Chicago bands. I’d gathered that they had ties to “alt-country,” but the cuts I heard on the radio were closer to 60’s pop, reportedly largely due to Bennett’s influence.

Fast forward a few years. Yankee Hotel Foxtrot came out. It may have been the last major label rock CD that made a notable amount of people agree that it was significant, and it convinced me enough that I bought it. Of course, it also represented a skirmish between Wilco and the major label, even if the result was only that they went from one division of the label to another, artier division. And, although he cowrote most of the songs, it was the end of Bennett and Wilco. I saw the film that covered it all, and a few people in the theatre booed when Bennett made some angry remarks.

By then, I was fairly busy with my own bands. And it came to pass that in 2003 Bennett mixed an album for one of them.

I remember the room full of old analog keyboards and other oddball music gear at Bennett’s studio (still in Chicago then, although he later went to the suburbs). I also remember the reel to reel machine with a few old Bee Gees tapes sitting near it (from their Beatlesque ballad period rather than the disco years). But my main memory is the time he decided to take a shopping cart full of bottles, set up a mic, and record the sound of the cart falling a couple stories onto a dumpster in the studio parking lot. This became the hidden track on our CD.

That was a hint of his wilder side. Other than that, he was a nice guy who did the job well.

I didn’t keep close tabs on him after that. Most of the news I heard was along the lines of a plan he had to put out three CDs in a year, and other things that sounded like he wasn’t finding his way to the right track. Meanwhile, Wilco continued, still very good, but perhaps a bit duller. Bennett’s absence wasn’t the only reason for that, but it may have been one.

Now Bennett is gone, and Wilco has an album which is the first one of theirs post-YHF that I doubt I’ll get right away. Meanwhile, my perspective on music changed over that ten-year cycle which is now over. Too soon.