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
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Sham-A-Ling-Dong-Ding
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.
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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:
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What Others are Saying
Very nice job on this Jesse page! He is missed
Just wonderful! What a life. Jesse your music has been such a giant part of my life, through ups and downs. Namaste.
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.
What an extraordinary talent ! Jessie had a humanness that very few people have. I’ll always be a fan of his.
I truly miss Jessie Winchester. I love his music. I was so broken hearted about his passing. RIP.
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…