“The word that comes to mind is grace.” – Elvis Costello
Jesse Winchester, a singer’s singer and a songwriter’s songwriter, died of bladder cancer on April 11, 2014, at the age of 69. His voice, by turns ethereal, sly, earthy, and heartbreakingly direct, delivered some of the finest songs of our time over more than four decades of live performance, and twelve original albums, including the forthcoming A Reasonable Amount of Trouble. His songs have been covered by artists as different as Jimmy Buffett, Elvis Costello, Reba McEntire, Wilson Pickett, Waylon Jennings, Emmylou Harris, Bonnie Raitt and the Everly Brothers.
Jesse Winchester was born May 17, 1944 in Bossier City, Louisiana, to James Ridout Winchester and Frances (Manire) Winchester. He spent his early years in Mississippi, and moved to Memphis with his family at age 12, where his father went to work with the Winchester law firm. There, Jesse’s ears were opened to the sounds of rhythm and blues and rockabilly via radio stations such as WDIA, where B.B. King and Rufus Thomas hosted shows, and WHBQ, where the irrepressible Dewey Phillips mixed the music of black and white acts in a glorious jumble. Jesse got his first guitar shortly after arriving in Memphis, and began playing in bands around town while attending Christian Brothers High School.
Winchester left Memphis to attend Williams College, from which he graduated (after a brief period studying, and playing with a band, in Munich, Germany) in 1966. Soon thereafter he received a piece of mail that would profoundly alter the course of his life – a draft notice summoning him to serve in Vietnam. Deeply disturbed by the war and the prospect of killing in what he considered a dubious cause, Winchester abruptly left the United States for Montreal, Canada, where he was to live for the next 36 years.
In Montreal he made his living first playing with various bands, including one called Les Astronauts, whose members were required to dress in spaceman costumes. Deciding that space travel was not his forte, he began to focus on solo performance and, more importantly, songwriting. The first song he wrote, “The Brand-New Tennessee Waltz,” set a very high standard, and remained a signature tune for him. It was eventually covered by Joan Baez, Ralph Stanley, the Everly Brothers, and, in 2000, Patti Page, who had recorded the original “Tennessee Waltz” fifty years earlier.
In 1970, his self-titled first album, Jesse Winchester, was released. Produced by Robbie Robertson and engineered by Todd Rundgren, the album contained several of Jesse’s most enduring and popular songs, including “The Brand New Tennessee Waltz,” “Payday,” “Biloxi,” “Yankee Lady,” and the haunting “Quiet About It.” The record firmly established his reputation as both songwriter and performer, and a succession of albums followed as he kept up a busy touring schedule through Canada, Australia, and Europe.
In 1977, President Jimmy Carter announced an amnesty for those who had left the country to avoid being sent to Vietnam, and Jesse was finally able to visit, and perform in, the United States. He did not, however, consider moving back. “I had a Canadian wife,” he said later, “Canadian children, and a Canadian mortgage.” Based in Montreal, he continued busily touring and recording through the 1980s.
On the eve of the 1990s, tired of touring, and with his songs being recorded regularly by top country artists such as Reba McEntire and Wynonna Judd, Winchester took nearly a full decade off from traveling and performing to stay home and concentrate on songwriting. At the end of that decade, Winchester recorded Gentleman of Leisure, an album containing his pick of the songs he’d written during that time. The record, produced by Jerry Douglas, remained one of Winchester’s favorites among his own recordings.
In 2002, he met his future wife, Cindy, and the next year moved back to the United States, settling in Charlottesville, Virginia, after a brief period in his old home town of Memphis. In 2007 he was awarded ASCAP’s prestigious Lifetime Achievement Award. He maintained a comfortable touring schedule and continued to write new songs, the best of which made up his 2009 album Love Filling Station.
But a 2010 appearance on Elvis Costello’s Sundance series Spectacle introduced Jesse’s music to a new and larger audience. Alongside Costello, Neko Case, Sheryl Crow, and Ron Sexsmith, Jesse performed several songs, most notably the stunning “Sham-A-Ling-Dong-Ding,” from Love Filling Station, a tender and shockingly beautiful ode to the nonsense lyrics in the teenage love songs of the 1950s. The performance literally stopped the show, according to Costello. “I just bowed my head,” the host said, “and told the audience that they had to go home because I could not gather myself to make the next introduction, such was supernatural beauty of his voice.” That performance quickly became a word-of-mouth sensation via YouTube, and Winchester’s performing schedule went into a higher gear.
That wave of activity was brought to an abrupt halt in June 2011, when Jesse was diagnosed with cancer of the esophagus. He underwent surgery and a brief but difficult treatment, which he faced with extraordinary dignity and spirit. Amazingly, in August of that year he was pronounced cancer-free, and he resumed his performing schedule. During his illness, an all-star group of artists recorded an excellent tribute album of Jesse’s songs, entitled Quiet About It. Jimmy Buffett, one of Jesse’s biggest fans, was the driving force behind the tribute.
In February 2014, cancer was found again, and this time it was untreatable. Jesse Winchester finally succumbed to it on April 11, 2014, at home – not alone, but surrounded by the presence and love of his wife, Cindy, and his family.
He is survived by his wife, Cindy, a brother, Cassius Winchester, and a sister, Ellyn Weeks, as well as his children, James Winchester, Alice Winchester, and Marcus Lee Winchester, a stepdaughter, Jennifer Slangerup, and his grandchildren Oliver, Gus, and Luke Dungavell of Ontario, Canada, and Tave and Vann Slangerup of Charlottesville, Virginia.
– Tom Piazza, author and family friend
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