Would the "real" Jay Bennett have been disappointed in me? The late guitarist was, by all accounts, a free-spirited soul who appreciated mischief and who didn't shy away from good-natured troublemaking. He might've gotten a laugh out of my misrepresenting myself—had I taken my many chances.

The real Jay Bennett, of course, is dead. I'm left with the name and an unending stream of jokes by in-the-know indie-rock types who apparently think they're, perhaps, the first to notice.

I realize some of you may be wondering who Jay Bennett is. He is the late musician/producer/songwriter who became known for helping turn the Chicago-based rock band Wilco into stars in the late 1990s. He died in his sleep on May 24 at the tender age of 45 after overdosing on the unsexy painkiller fentanyl. He was best known for expediting the musical maturation of Wilco, taking Jeff Tweedy's act from a by-the-numbers alt-country band to the standard-bearing Americana band, then to a genre-defying Baroque pop band in the early 2000s.

The real Jay Bennett, not the author.
The real Jay Bennett, not the author.

By the time Bennett was fired from Wilco, immediately after the recording of the band's masterpiece, Yankee Hotel Foxtrot, the multi-instrumentalist was rightly regarded as a musical great on the same level as the band's leader, Tweedy. Clearly, these two highly gifted musicians could not co-exist in the same band, as you can see if you watch Sam Jones' documentary I Am Trying to Break Your Heart.

When Tweedy fired Bennett from Wilco in 2001, I was living on Chicago's near-west side, working as a copy editor at a newspaper based just a few miles from Bennett's suburban hometown of Rolling Meadows and, like the "real" Jay Bennett, playing guitar in a Chicago-based rock band.

And, yes, our paths crossed.

On the day the news of Bennett's Wilco departure broke, I returned home to find a message on my answering machine. It was from Jim DeRogatis, the longtime rock critic for the Chicago Sun-Times and author of the Lester Bangs biography Let It Blurt. My first thought: "Why the hell doesn't DeRogatis have the real Jay Bennett's phone number? Does he really have to use the white pages to find the digits of one of Chicago's biggest rock stars?"

My next thought: "Should I call back? Has DeRogatis tracked down the real Jay by now?"

I guess I'd always considered myself a fan of the sort of subversive humor that could be wrung from a situation such as this. Then I considered the possibility that my posing as Jay Bennett in a phone interview would simply make me look like a dick. Plus, as someone who's worked for newspapers his entire career, what would such a trick say about my journalistic integrity?

I can't recall whether the Sun-Times' story the next day contained a quote from Bennett. I think it didn't. I blew my chance. Who knows what sort of weird problems any comments I made could have eventually caused, given that Bennett's departure eventually became the subject of a lawsuit aimed at Tweedy? Could something I said have been used by an unwitting attorney in a brief? Could I have been subpoenaed to testify? Could the wrinkle I added to the case have been the subject of a snarky Pitchfork news brief?

Who knows? I didn't do it, which, I fear, would've left the "real" Jay Bennett disappointed in me.

Though I played guitar in a band that gigged regularly, I'm merely a hobbyist with nowhere near the musical chops of my namesake. Still, I know how to play guitar, and that made it all the more difficult for me when, over the course of the next year, I received a handful of calls from people seeking Bennett's services. Most were recording studios asking the musician to swing by and lay down some guitar tracks for commercial work. One was an engineer wondering whether Bennett would like to do a guest track on some local artist's new CD. I probably could have signed a contract via fax, then showed up and filled out a W-9. Perhaps I could have made some nice coin or, at the very least, caused a hilariously awkward encounter with some poor engineer. It's possible I could have slipped past the right combination of naïve people and still have royalty checks coming in.

At one point, I needed to repair the Marshall 50-watt amp I'd been using, so I dropped it off at one of Chicago's top used-guitar-and-amp shops. A couple of days later, I got a call from the amp tech wondering whether I was you-know-who, because they had some of his other gear sitting around the shop. An unscrupulous version of me could have probably picked up the amp by flashing my driver's license to just the right clerk, then made a mint selling it on eBay.

Again, I wonder, why didn't any of these people have Jay's phone number? Especially since he was becoming a sought-after session musician and record producer. I'd heard that he was working on a solo record and he was playing sporadic live shows with artists like Edward Burch and fellow former Wilco member LeRoy Bach. I began to hear music-scene gossip about Bennett's personal problems, including bouts with substance abuse. Friends told me I'd probably run into him sooner or later if I went out frequently enough.

On January 4, 2003, that happened. The band I played in, The Paperbacks, was to open for The Reputation (the band Elizabeth Elmore started after Sarge broke up and she went to law school) at one of Chicago's great rock clubs, Schuba's. Before we played, someone told me that the real Jay Bennett was going to be sitting in on keyboards with the headliners for a handful of songs. Finally! Chicago's two Jay Bennetts (one arguably a pop music genius and the other, inarguably, a hack) on the same stage on the same night.

We performed to an appreciative crowd that was quickly growing in anticipation of The Reputation, whose own star had been rising over the past year after relentless touring. I still hadn't spied Jay, even backstage. At Schuba's packed bar, which is separated from the music room, the singer of my band (who later became my wife) was drinking PBRs and doing a shot of whiskey with, unbeknownst to her, another Chicago rock legend, David Yow of The Jesus Lizard.

I went over, and she introduced me to "Dave." I said I knew who he was and it was an honor to meet him. That's when I saw the real Jay Bennett over her shoulder. Even though I was talking to David Yow (!), I excused myself to approach Jay, who was coming out of the bathroom.

The rumors about the man who'd made Wilco's Summerteeth into a pop masterpiece were true. He looked like a wreck. He was wearing a ratty down vest, and his glasses were dirty. He was drunk, for sure. Seemingly high on something too. His hair was long and stringy. As I leaned in to talk into his ear, I smelled his unlaundered flannel shirt. This was Chicago in January, but he was sweating. And he couldn't stop running his hand through his filthy hair.

"Hey, Jay. My name is Jay Bennett too. My band played here earlier tonight."

"Wow, man. We have the same name. Sorry I didn't see your band."

"Yeah, I wanted to meet you because I'm a fan and, also, I've been getting calls meant for you. DeRogatis a while back; guys who've wanted you to lay down some guitar tracks."

He laughed a woozy laugh. "Oh, man, you should've done it. You could've done it. Did you give 'em my number?"

"No, I don't have your number."

"Hey, man, lemme give it to you in case someone wants me to play."

He scrawled his number on a piece of lined notebook paper and handed it to me. Someone came up to us and said, "Jay, you ready? They're ready for you." The Reputation had already played a few songs, and it was his time to join them. He stumbled into me for a drunken hug and said, "Give 'em my number if they call."

He walked into the music room and onto the stage to a nice ovation. I thought about sticking around to talk to him again, but I knew there wouldn't be much else to talk about—if he'd even remember me.

After Jay died of an accidental overdose of fentanyl, a drug often prescribed to treat chronic back pain, I received a not-unexpected flood of messages: "Hey, I heard you died." "Did you hear about your death?" "Jay, are you really dead?"

I saved the phone number for several years, but I never did get another call from writers, musicians or studios looking for Jay. Within a couple of years after that meeting, neither of us lived in Chicago anymore. I moved to Phoenix, and he moved back to his native downstate Illinois, where he would eventually die. I guess that's when I finally threw away his number.

Now I'm left with the name and the burn of opportunities missed. But at least now there's no more confusion between the hack Jay and the genius Jay.

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