By Jeremy Hallock
By James Khubiar
By Observer Staff
By Kelly Dearmore
By Jim Schutze
By Rachel Watts
By Lauren Drewes Daniels
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.