The first album recorded by Jeff Tweedy's band Wilco was called "A.M." Released on March 28, 1995, it came not long after the breakup of Uncle Tupelo, the influential trio from Belleville, Ill., that included Tweedy with his high school pals, Jay Farrar and Mike Heidorn.
"A.M." was a pleasant continuation of the Uncle Tupelo sound -- country-adjacent indie rock with a working class, small-town sensibility. But it tends to get short shrift in the Wilco canon because of the albums that followed -- "Being There," "Summerteeth" and "Yankee Hotel Foxtrot" -- a towering trio of adventurous, imaginative albums that laid waste to the quaint, shaggy little brother rep that clung to Tweedy in Uncle Tupelo's wake.
Helping Tweedy stretch his sonic ambitions on those post-"A.M." masterpieces was Jay Bennett, a dreadlocked, chain-smoking, musical polymath and studio wizard who was working at an electronics store in Champaign, Ill., when he signed on with the band.
His approach to making records was like Brian Wilson crossed with Jim Dickinson -- "Smile" meets "Third/Sister Lovers" -- equal parts intricate and sloppy with a true record nerd's enthusiasm and fearlessness. He wouldn't think twice about recording the sound of bashing a radiator with a metal pipe, the plinking keys of a toy keyboard or dropping a hammer on a piano if he thought it might help a song.
Bennett and Tweedy's relationship would implode, and his departure from Wilco was detailed, sometimes cringingly, in "I Am Trying to Break Your Heart," director Sam Jones' 2002 documentary about the band and the fraught process of recording "Yankee Hotel Foxtrot."
Now the late multi-instrumentalist, who was just 45 when he died on May 24, 2009, is the subject of "Where Are You, Jay Bennett?," a documentary directed by Gorman Bechard and Fred Uhter. This is familiar ground for Bechard, who has directed indie documentaries about beloved trash-pop punks The Replacements, the late Husker Du drummer Grant Hart, Ohio singer-songwriter Lydia Loveless and Sarah Shook & the Disarmers.
The doc, released April 19 on DVD and pay-per-view, is a tender appreciation of a musician who died way too young. It features interviews with former Wilco drummer Ken Coomer, Billy Bragg, Bennett collaborator Edward Burch, Tim Easton, Bennett's brother Jeff, writer Greg Kot and more.
BENNETT'S VOICE
Bennett's voice is heard on old video and audio interviews and performances. He is also represented in a series of minimalist, watercolor animation sequences by Edwin Gendron. No current Wilco members are included, though they appear in old footage, and Tweedy's voice is used from his reading of the audio version of his 2018 memoir "Let's Go (So We Can Get Back) A Memoir of Recording and Discording with Wilco."
Bennett was a happy, if obsessive, child. His mother, Janis, tells of how as a preschooler he wore the same red, button-down shirt every day until it fell apart, and then continued to wear it as a vest, with its frayed cuffs pinned to another shirt. He was so enthralled by Maurice Sendak's children's book "Where the Wild Things Are" that a teacher finally asked his mother to have him stop checking it out of the library so other kids could read it. As an adult, he had a serious affinity for ketchup, pouring dozens and dozens of packets over triple orders of McDonald's fries.
Music took hold early on, and Bennett passed on an eighth-grade class trip to Washington to buy his first guitar. He took a few lessons, but was mostly self-taught, which is how he would later learn piano and other instruments. An early band was named The Robesmen because they raided the Bennett family closets for house robes to keep warm while playing in the basement. He was a tinkerer, working on the vintage Toyota Corollas he and his father loved as well as musical gear. He was also sharp in the classroom, earning degrees in secondary education, mathematics and political science.
He helped start power pop quartet Titanic Love Affair, which recorded three albums, and was a member of twangcore outfit Steve Pride and His Blood Kin before joining Wilco, first as a touring guitarist and then as a full-fledged member.
Bennett would help shape Wilco's sophomore effort, the sprawling double album "Being There," but his influence on the band would really be felt on "Summerteeth," the 1999 record that featured not only his playing, but also his multi-layered, orchestral-pop arrangements alongside Tweedy's often dark lyrics. It was around this time that his collaboration and friendship with Tweedy was at its most intense, a period that Coomer says made the others in Wilco, including fellow founding member and bassist John Stirratt, feel like sidemen.
But tensions -- musical and personal -- were growing, and by the end of the recording of "Yankee Hotel Foxtrot," in which Bennett was acting as band member, songwriter and engineer, Tweedy fired him. Some of this played out dramatically in "I Am Trying to Break Your Heart," though several of those interviewed in the new documentary say the portrayal of Bennett -- who comes across as manic and controlling in Jones' movie -- is unfair.
Wilco grew into the American rock 'n' roll institution it is today, releasing critically acclaimed albums, touring and growing a loyal fan base. Bennett's post-Wilco profile wasn't nearly as prominent, but he continued to make music and released five solo albums. A sixth record, "Kicking at the Perfumed Air," was put out after his death.
HIS DEMONS
There are somewhat frustrating allusions in the documentary to Bennett's "demons" and "rock-and-roll excesses," but nothing is ever followed up on other than brief suggestions that he struggled with drug use and alcohol. It would have been helpful to dig a little deeper into this to learn more about him, but the filmmakers let it go. And there is no mention of the breach-of-contract lawsuit Bennett filed just before his death against Tweedy seeking payment of $50,000 in royalties Bennett claimed he was owed.
The film does help clear up Bennett's last days, and corrects the impression of a drugged-out musician who couldn't afford health insurance. After years of jumping around onstage, Bennett was in great pain and needed hip-replacement surgery. Since his insurance company deemed his condition pre-existing, he began selling some of his musical gear and worked out a plan to pay for the procedure. In the meantime, he was prescribed a fentanyl patch to wear on his skin to help manage the pain. The patch, which he'd worn less than 24 hours, leaked and he died of an accidental overdose.
It's such a tragic end. Watching the movie, one can't help but wonder what more he could have accomplished, what roads he could have traveled. How would a Phoebe Bridgers record or a Felice Brothers project sound with Jay Bennett producing? Maybe he would have mended fences with Tweedy and sat in on a Wilco show here and there. Perhaps he would have found that perfect combination of collaboration and autonomy in his solo work and reached a larger audience.
His family and friends say that, despite his physical problems, Bennett seemed to be turning a corner before his death. He'd made a commitment to getting healthy and opened his own recording studio, Pieholden Suite Sound in Chicago, (named after a "Summerteeth" song) which is still in operation.
"His head was in a better spot than it had been in years," Burch says, an observation that is both reassuring and sad.