Jay Bennett

I don’t know why, but whenever a musician passes on who never got his full due while alive, I’m on it. The last time I felt this way was for Sean Costello, the young blues guitarist who was just starting to find his voice before checking out in a run-down hotel room in Atlanta. When Ronnie Lane passed on quietly in a small town in Colorado, that hit me like a thunderbolt, as I had spent the past few years discovering the great music he made after leaving The Faces.

And, now, Jay Bennett, formerly of Wilco, checks out far too early. Not sure if it was misadventure or on purpose, but I don’t think anyone’s scoring that too closely. He was a year older than I am, which I found shocking … thought he was much older than I was, or I was much younger. He always seemed so middle-aged, probably due to his body type and big head. He had one of those burly midwestern bodies and head, you could picture him in a pair of horn-rim glasses, a black leather hat with ear flaps and a big-ass Woolrich coat. Shoveling snow, or selling newspapers on the corner in Chicago, or bouncing a niece on his knee at a cookout. The dreadlocks were out of place on him, but that was his thing, to be this typically midwestern-looking guy who had a lot more going on.

Apparently, he was in the process of suing Wilco over the issue of royalties related to his appearance in the documentary I Am Trying to Break Your Heart which, let’s face it, has created this “story” about Jay and the band that will be his legacy. (Jay was also needing a lot of money for a long-delayed hip operation, without health insurance.) In the documentary, Jay is made out to be this mad genius, constantly smoking, who spends all his time in the studio and eventually gets too nuts for Jeff Tweedy to deal with, so he’s asked to leave the band. We never get to see this happening. Sure, there’s a scene where Jay’s fretting over an intricate segue between two of the songs, complete with Tweedy vomiting in the rest room when the tension over their disagreement on this issue boils over, but that didn’t seem all that harsh to me. If you know bands, you know that break-ups tend to result over a long period of fights and issues that make stuff like that passage seem like small change. Whatever caused Jay to be dumped from the band, we didn’t see it happening.

And that’s a shame, because Jay was responsible for pushing the band to its creative peak, with Summerteeth and Yankee Hotel Foxtrot. Only the band knows for sure, but both those album, Jay’s presence is all over them, whether as a songwriter, arranger, producer or musician. When he left the band, that musical density and greater pop sense disappeared with him. I still love the band, but you can hear what Jay meant to them when he left. This two-part interview from Glorious Noise – the first part letting Jay expound upon why he left and the second outlining exactly what he did on Yankee Hotel Foxtrot – gives excellent insight into just how integral his role was to the band.

I’m guessing his imprint was even larger on the previous album, Summerteeth, which many fans consider the band’s peak. I do, too, although I didn’t think much of the album at first. Brother J was a Wilco fan before I was, because of their alt country beginnings, but Summerteeth, he threw his hands up and said fuck these guys. Their previous album, Being There, was considered their creative breakthrough, and even then, Jay’s imprint was being felt in more loose/trippy arrangements. I know more than a few people who couldn’t stand this sort of “branching out” and thought the band was over-rated, but there are certain songs like “I Got You,” “Red Eyed and Blue” and “Dreamer in My Dreams” that are the sound of a band hitting its stride.

Jay leaves the band, and Tweedy veers Wilco into a more lean, less poppy direction. Which I still love. Every time I listen to Wilco, I feel like I’m listening to a guy, Tweedy, who really likes marijuana. Everything he does is trippy in a way suggesting that intelligent, but slightly askew take on the world so many heads have. But you can hear that pop sense Jay imparted greatly decreasing, and when Jay was with Wilco, he was writing material that’s about as good as pop music gets. Two songs in particular represent Jay’s creative peak.

“My Darling” from Summerteeth underlines the issues so many older Wilco fans had with the band: too much shit going on. I recall Brother J’s reaction to Yankee Hotel Foxtrot: “These guys are writing basic songs that sound fine and then lumping all this sonic shit on top of it to make it sound experimental.” Which he thought was bullshit, and sometimes it was. This was truly the case for “My Darling,” which was mostly Jay’s song, maybe all Jay’s song from what I gather, and if you want to hear the best version, try this one from his first post-Wilco album, The Palace at 4 am. Less is more in this case – I put this song on the same shelf as “Imagine” by John Lennon. It’s that good! To come up with a melody that basic that hasn’t been used before, to me, is a sign of someone who has the ability to function on a higher creative level than most musicians.

The absolute best, though is “California Stars” from Mermaid Avenue. I don’t know what Jeff Tweedy has to do with the song, and I suspect that asshole Billy Bragg just sat in a corner strumming an acoustic guitar. It’s my understanding that this was one of Jay’s song, too, with lyrics, of course, by Woody Guthrie. “California Stars” is one of those songs that defined the 90s for me, maybe the best song of the 90s, along with other songs like “Creep” and “Common People.” First time I heard that song, it made perfect sense: that sad, floating feel that did impart someone looking up at a night sky and wishing he was back in California. The lap steel work by Corey Harris is also outstanding, really makes the song.

Those two songs alone put Jay Bennett on a higher plane for me. He didn’t stop making music after Wilco either, putting out solid solo albums that had flashes of the same brilliance. Try “My Little Wicked One” and “Hank,” which now takes on new meaning. I hadn’t known it at the time, but Jay’s musical presence was in my life back in the early 90s. Brother J had read a review of the band Titantic Love Affair that compared them favorably to The Replacements, with their first album having a cover designed by Chris Mars. “Planet Strange” was their big song, and they weren’t quite The Replacements. I never warmed up to that album; it just wasn’t on quite the same level. Still, that’s Jay Bennett, skulking under his straggly hair in the background. I think Brother J still has that CD back home in his rack, although I’ll bet he hasn’t looked at it, much less played it, in years.

His legacy will always be the work he did with Wilco which, of course, will be tainted by the negative vibe attached to his departure. I’m watching I Am Trying to Break Your Heart right now, and it still seems like Jay got a raw deal, although, again, none of us have any idea what went down between him and Jeff to blow things apart. Like most bands, Wilco seems like a strange beast, full of guys jockeying for position and “yes men-ing” it to maintain status quo in that floating perception of power within the band. Which never seems real until you’re thrown out on your ass. I gather being in a band is like being in a reality TV show, like Survivor, where you can tell yourself this isn’t real, but it is. I would never do these things in my real life, you tell yourself … but this is your real life. The camera following you around is your fame, your image, and it’s always watching you and influencing how you act. I don’t think Tweedy or Wilco are bad people at all – quite the opposite. But I’d gather they’re a bit fucked up, like all bands are, which is what happen when you travel around for years in a bubble with the same people all the time.

But poor Jay punches his ticket over the Memorial Day weekend. He deserves better than to be thought of as some talented crank who talked his way out of a great band. He wasn’t full of shit regarding his place in the band, as it became evident how important he had been when he left, and the band’s direction took a sharp turn. Summerteeth will be like summer itself, representing a time and place that stays the same while you go on, or don’t go on. Man, Jay looks like hell in this documentary, constant cigarette, hangdog face, clearly some kind of drug usage going on. Ditto Tweedy, they look like hell. But that hell they put themselves through left behind some great music. I don't doubt Jay was a pisser to work with, but the end results speak for themselves. Hats off, Jay.