“I’m dying to find Him, but dying’s my fear. Is there perfection? Will there be pain? Will I see mom and dad again?”
With a weathered voice, steeped in the honest emotion of a man facing his mortality, Jesse Winchester seeks answers from his Maker during these poignant lines in the song “Just So Much.” It’s the closing track on his final album A Reasonable Amount of Trouble, posthumously released on September 16.
Winchester, a prolific singer-songwriter throughout a 45-year career, died on April 11 after a battle with cancer, just a few weeks before his 70th birthday. The successful tunesmith, who possessed a delicately impactful voice and had his songs covered by the likes of Joan Baez, Jimmy Buffet, Waylon Jennings, Elvis Costello and The Everly Brothers, lived in Charlottesville in his later years.
With 11 studio albums to his credit, Winchester made his final effort in the spring of 2013, while in remission from esophageal cancer that had been diagnosed two years earlier. As a result, the new album certainly addresses the fragility of life, but Winchester didn’t want introspective ballads like “Just So Much” and “All That We Have Is Now” to dominate the whole set. He also decided to lighten the mood with the dance-friendly rocker “Never Forget to Boogie” and an endearing take on the classic oldie “Whispering Bells.”
“At the time we recorded he was weak, but he had just gotten a clean bill of health, so he was happy,” said producer Mac McAnally, who also played guitar on the album and helped Winchester find additional backing musicians including Grammy-winning dobro master Jerry Douglas. “The saddest of Jesse’s songs has humor, and the happiest of his songs has a little bit of pathos and sting. That’s just how he wrote. He had the full circle of life in almost every song.”
Winchester’s journey toward a music career started in 1967, when he left his home in Memphis, Tennessee and moved to Canada to avoid fighting in Vietnam. Up north he met The Band’s Robbie Robertson, who produced Winchester’s debut self-titled album. The effort included some of Winchester’s most beloved tunes, including “The Brand New Tennessee Waltz” and “Biloxi,” which became a staple for Buffet. At first unable to play in the United States, Winchester was eventually granted amnesty by President Jimmy Carter. He first performed in the U.S. in 1977 and went on to have a Top 40 hit with the song “Say What” in 1981.
He settled in Charlottesville with his new wife Cindy in 2002 and re-emerged after a nine-year absence from recording with the 2009 album Love Filling Station.
Unfortunately Winchester’s dormant cancer returned, found in his bladder this past winter. He became too weak to finish the final production touches on A Reasonable Amount of Trouble but trusted McAnally to get the album ready for release. Before he died Winchester was able to have a listening party with his family and then sent his producer a note of approval.
“He said, ‘I wouldn’t change a single note,’” said McAnally, also a well-known songwriter and session player who’s worked with Buffet and Kenny Chesney. “That’s a big deal for me. That e-mail from Jesse is as valuable of a thing to me as I’ve ever had in the music business.”
While never quite a star, Winchester was deeply respected by his peers. Bob Dylan once said of him: “You can’t talk about the best songwriters and not include him.”
That’s a compliment that’s probably worth more than any official accolades, even though Winchester earned some, including Juno nominations and a Lifetime Achievement Award from the American Society of Composers, Authors and Publishers. When Winchester’s illness was first diagnosed Buffet and Costello—with help from McAnally —decided to put together a tribute album to support their friend. Released in 2012, Quiet About It features Winchester’s most influential songs interpreted by James Taylor, Allen Toussaint, Rosanne Cash, and many iconic musicians.
“He’s one of my heroes,” McAnally added. “One of the hardest things to do in this business is have a consistent body of work. You can go anywhere in Jesse’s work, drop the needle and find someone representing the best thing about human nature, writing in a masterful way.”