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What Jay Bennett’s Death Made Me Realize About Wilco

A few Sundays ago I hosted a Wilco listening session in my apartment.

The only guest was my husband, a casual listener more conversant in Jeff Tweedy’s migraines and squabbles with sidemen than the band’s actual musical catalogue. As a longtime Wilco fan — who first heard A.M. on a dorm boombox freshman year at college in Chicago — I took it upon myself to school him.

More on >> Former Wilco Member Jay Bennett Dies at 45 >> Listen to Wilco’s New Album! >> Download: Wilco and Feist Cover Woody Guthrie >> Springsteen, Beastie Boys, and Phish Headline Bonnaroo ?I pulled out all six of their albums, put them in the carousel (they’re one of the few bands whose records I always buy on CD) and walked him through each song. By the time we moved from the atmospheric pop of A Ghost Is Born into the jammy folk-rock of Sky Blue Sky, I had a sudden realization: I liked Wilco better with Jay Bennett in the band.

When I heard that he died last Sunday, this wistfulness turned into something worse. Bennett, who released a handful of quirky and gorgeous (but largely overlooked) solo albums after his dismissal from Wilco, had emerged in recent media as a vengeful and troubled soul. Just three weeks prior to his death, he filed suit against Wilco for breach of contract and unpaid royalties, possibly to help pay for hip surgery he lacked health insurance to cover. While a toxicology report has yet to determine the cause of death, his drug history and the pain he was likely in certainly raise the specter of an overdose. Which only makes his clouded reputation as an artist seem more unfair.

To me, Bennett got a bad rap. Much of this comes from his portrayal in the documentary I Am Trying to Break Your Heart: as a crazy, dreadheaded, obsessive, control freak — a guy all but explicitly blamed for sending Tweedy into the bathroom stall to puke his guts out, overwhelmed by the angst of working with such a nightmare. That Tweedy then fired Bennett only cemented the latter’s rep as an albatross cast from Tweedy’s shoulders so that Wilco could rise to glory.

The film is a must-see (especially for anyone considering a career in the music industry), but it has its distortions. (Watch the trailer here.) Even Tweedy complained that it focused too much on his and Bennett’s relationship. And the Bennett-as-creativity-squelcher throughline sort of obscures the fact that he co-wrote eight of the eleven songs on Yankee Hotel Foxtrot, the album that propelled Wilco to become one of the most critically lauded and obsessively followed bands of their generation.

Bennett joined Wilco in 1994 just after they recorded their debut, A.M. While it’s not always easy to pinpoint one musician’s effect on a band’s sound, I think Bennett’s contributions were audible and distinct.

A multi-instrumentalist and studio wiz, he helped Wilco shed its alt-country tag and move into the immersive, unclassifiable sonic territory they become known for. Bennett’s Wilco debut Being There was a huge step forward, and by the time Summerteeth came out in 1999, they sounded like a completely different band. The songs were fuller, warmer, the standard guitar-and-drums set-up of A.M. had been supplemented by a lush psychedelic impressionism that was largely a product of Bennett’s masterful work with farfisa organ, bells, Moog, lap steel guitar, banjo, synthesizer, and other instrumental exotica.

Yesterday I listened to Summerteeth and tried to imagine it without these contributions. How would “Can’t Stand It” sound without those dramatic bell chimes that double the guitar chords at the opening? Would “I’m Always in Love” be half as good without the chirpy, Cars-ish analog synth? And would “She’s A Jar” be anywhere near as heartbreaking without that soft, sighing organ that coos through the verses? Or those stately, orchestral synths that rise to bring in the chorus? Or that gentle oboe-like keyboard phrase that caresses the line “dry your eyes, you poor devil”?

Go listen to that song now, think about Jay Bennett’s passing, and try keeping your own eyes dry.

I’m not trying to take glory from Tweedy. Wilco is his band, and boy has he earned the rep they enjoy now. But I really think Bennett made him better, and at a crucial time in the band’s career. I still love Wilco. I’ve enjoyed all their post-Bennett albums and think their new one, Wilco (The Album), is the best of those yet. But I haven’t felt that way about any of them. It always seemed like something was missing to me. Maybe it was just a certain deeply musical understanding of the songs’ shapes and colors, a certain way of setting off a phrase or building a gorgeous aural frame. I’m not exactly sure. But now that something is gone for good.