Jesse Winchester

Jesse Winchester was a singer’s singer and a songwriter’s songwriter. His voice, by turns earthy, ethereal, sly, and heartbreakingly direct, delivered some of the finest lyrics of our time over more than four decades of live performance, and thirteen original albums. A gentle man, soft-spoken and courtly, he projected a quiet strength in performance. His songs have been covered by artists as different as Jimmy Buffett, Elvis Costello, Reba McIntyre, Wilson Pickett, Waylon Jennings, Emmylou Harris, Bonnie Raitt and the Everly Brothers.

You can’t talk about the best songwriters and not include him. – Bob Dylan

Jesse Winchester was born May 17, 1944 in Shreveport, Louisiana, to James Ridout Winchester and Frances (Manire) Winchester, a family with deep Memphis roots. He spent his earliest years in Mississippi but moved to Memphis, with his family, at age six. In Memphis, 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.

Early Years in Memphis
Interview provided courtesy of the New Orleans Jazz & Heritage Foundation Archive

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.

Going to Williams College
Interview provided courtesy of the New Orleans Jazz & Heritage Foundation Archive


In Montreal, after playing with various bands, including one called Les Astronauts, whose members were required to dress in spaceman costumes, Jesse 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.

Moving to Montreal
Interview provided courtesy of the New Orleans Jazz & Heritage Foundation Archive

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.

First Song Written: Brand New Tennessee Waltz
Interview provided courtesy of the New Orleans Jazz & Heritage Foundation Archive

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. Based in Montreal, he continued busily touring and recording through the 1980s.

Jesse Winchester performs “The Brand New Tennessee Waltz” on Elvis Costello’s Television Series Spectacle: Elvis Costello with…
Courtesy Spybox Media


On the eve of the 1990s, tired of touring, and with his songs being recorded regularly by top country artists such as Reba McIntyre 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.

Songwriting, Recording, Touring
Interview provided courtesy of the New Orleans Jazz & Heritage Foundation Archive

In 2002, he met his future wife, Cindy, and the next year moved back to the United States, to his old home town of Memphis. The couple ultimately settled in Charlottesville, Virginia, where Jesse maintained a comfortable touring schedule and continued to write new songs, the best of which made up his 2009 album Love Filling Station.

Artists Covering His Songs
Interview provided courtesy of the New Orleans Jazz & Heritage Foundation Archive

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; it quickly became a word-of-mouth sensation via YouTube, and Winchester’s performing schedule went into a higher gear.

Jesse Winchester performs “Sham-A-Ling-Dong-Ding” on Elvis Costello’s Television Series Spectacle: Elvis Costello with…
Courtesy Spybox Media

Jesse Winchester

That wave of activity was brought to an abrupt halt in June 2011, when Jesse was diagnosed with cancer of the esophagus. He underwent a brief but difficult treatment, which he faced with extraordinary dignity and spirit. 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, including Costello, Jimmy Buffett, James Taylor, Roseanne Cash, Allen Toussaint, and Lucinda Williams, recorded a tribute album of Jesse’s songs, entitled Quiet About It. Buffett, one of Jesse’s biggest fans, was the driving force behind the tribute.

Gentleman of Liesure
Jimmy Buffet

Jimmy Buffet’s cover of Winchester’s song “Gentleman of Leisure,” from the tribute album Quiet About It released on Buffet’s label, Mailboat Records.

In February 2014, Jesse’s cancer returned, and he finally succumbed to it in April of that year. His posthumous album, A Reasonable Amount of Trouble, was released late in 2014 , garnering two Grammy nominations.

From Winchester’s GRAMMY-nominated album A Reasonable Amount Of Trouble, including “Just So Much” nominated for Best American Roots Song:

All photos courtesy Winchester Family Collection

What Others are Saying

  1. Very nice job on this Jesse page! He is missed

    Steve Alexander
  2. Just wonderful! What a life. Jesse your music has been such a giant part of my life, through ups and downs. Namaste.

    James Graham
  3. I got to meet Jesse at the Moonshadow in Decatur, Georgia, in the early 80s. I’ve been listening to his music for decades now, and named my youngest son Jesse, who was born in 26 October, 1977. I plan on adding more of his great work to my song collection.

    Sally Bastien
  4. What an extraordinary talent ! Jessie had a humanness that very few people have. I’ll always be a fan of his.

    William E. James
  5. I truly miss Jessie Winchester. I love his music. I was so broken hearted about his passing. RIP.

    Stefan Barboza
  6. I have been struggling Jesse. You bring the grooves that heal. And there has never been nor will ever be a voice like yours on the planet. Thank you for your soul, your grace, the feel you bring to your music and the songs. Always the songs. I’ll show you where it hurts…

    Kris's Light

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