Jesse Winchester Has Died
He was not on the list.
We’re sad to report that songwriter, singer and guitarist Jesse Winchester died on Friday, April 11th, 2014, after a long battle with cancer.
Jesse first appeared with a debut album produced by Robbie Robertson of The Band. It had a gatefold cover and sported the same b&w picture on all four faces of the package, as if he’d shot his photon wad in one snap! It resembled the Americana look of the pictures of The Band on their second album. All it took was one listen to know this was a most special artist.
That first album was loaded with shimmering gems from the opener “Payday” through “Biloxi,” “Snow,” “The Brand New Tennessee Waltz,” “Yankee Lady” and the rest of the 11 songs there. It was an instant treasure!
Turned out Jesse Winchester was a Bossier City, Louisiana, native who had fled the US in 1967, relocating to Montreal to avoid being drafted to serve in the Vietnam War. An act of conscience. But politics never got much play in Jesse’s songs which were more images of the life, the land he’s left behind, and the life he had come to lead. During the time he was a draft exile, there was no chance he’d be able to come back to the States to play live, but that was finally corrected in 1977, when Jimmy Carter offered amnesty to conscientious exiles like Jesse.
Winchester was never a very prolific artist. Over 30 years
he only released 10 albums of songs, with one more to come as Appleseed Records
will soon issue his final album, A Reasonable Amount of Trouble (the title
inspired by a Sam Spade quote from The Maltese Falcon). There are also several
live albums available, too. Every album Jesse made was a gem, each studded with
terrific songs.
And those songs reflected the man he was: quiet spoken, with a most genteel, courtly nature … but with a rascally streak that surfaced from time to time, as in “Talk Memphis” and “Rhumba Man.” A Jesse Winchester concert was always a treat. I only had the chance to spend some quality time with him once. It was a night around 1996 when he did a live concert on WHYY-FM in Philadelphia. This was aired live, and as chance had it I was filling in for regular host Gene Shay. He came to the studio for an interview after the show, and I was utterly charmed and delighted by this soft-spoken Southern gentleman who had been so long removed from the land that shaped him. It was an evening I treasured ever since.
Any live performance by Jesse Winchester was a treat. Whether playing with a band, as he did early on when he could tour at last, or solo as he was most likely to do in recent years. Jesse was a riveting performer who would tell stories along with the songs, letting his warm, occasionally wicked wit shine. The proof is right there in those live recordings.
Emmylou Harris was one of the first to cover Jesse’s songs when she did gorgeous takes of “Defying Gravity” and “My Songbird” on her Quarter Moon in a Ten Cent Town album. Later Emmylou named her retrospective boxed set Songbird. In 2012, as Jesse was expecting to die from esophageal cancer, he received word Jimmy Buffett and Elvis Costello had shepherded a wonderful 11-song tribute album called Quiet About It: A Tribute to Jesse Winchester. Much to everyone’s surprise and delight, Jesse recovered and he was able to get back on the road.
But the cancer did finally return, and now Jesse has departed. Still, the gift of his wonderful songs remains … as does the memory of the sweet, kind, warm human being he always was. He could have let anger drive his songs but chose love instead.

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