Jesse Winchester, who fled to Canada in the 1960s to avoid the military draft and later became renowned for writing and performing intimate, touching songs that evoked his native South, died April 11 at his home in Charlottesville, Va. He was 69.
His death was announced by his manager, Keith Case. The cause was bladder cancer.
Mr. Winchester, who was one of the most respected singer-songwriters of his generation, recorded more than a dozen albums and had a substantial career as a performer.
He was probably best known, however, as a tunesmith of lyrical, sensitive ballads such as “Biloxi,” “Mississippi, You’re on My Mind” and “The Brand New Tennessee Waltz.” His songs were recorded by such diverse performers as Wilson Pickett, Waylon Jennings, Reba McEntire, Elvis Costello, Bonnie Raitt and the Everly Brothers.
“Jesse has an absolutely indelible place as a brave and lyrical songwriter who always shot straight to the heart,” the writer and critic Tom Piazza said Saturday in an interview.
In 1967, when he was 22, Mr. Winchester received his draft notice. Opposed to the Vietnam War, he boarded an airplane for Montreal instead, taking with him $300 and an electric guitar. He would live in Canada for more than 35 years, becoming a citizen in 1973.
“You have to remember that I wasn’t a musician when I went to Canada,” he told The Washington Post in 1977.
“If I had remained in America, I doubt that I’d ever have written a song or made any records. I just kind of drifted into music.”
Believing that his Southern accent kept him from finding steady work in Canada, Mr. Winchester turned to music as an afterthought, joining a French-language band in Quebec. He settled in Montreal, married and began to raise a family.
He lived his life in French, but when he retreated to his piano and guitar, the songs came out as pure reveries of the land he had left behind, seemingly forever.
“In a way, living in Montreal, in another culture, speaking another language,” he told The Post, “is what makes it possible for me to write about the South. It gives me distance, a perspective I wouldn’t have if I were there.”
Mr. Winchester began to perform at coffee houses and, in 1970, recorded his first album, which showcased his soft, whispery tenor voice. The first song he wrote was “The New Tennessee Waltz,” which was later recorded by Patti Page, who had a hit with the classic “The Tennessee Waltz” in the 1950s.
Another of Mr. Winchester’s early efforts was “Mississippi, You’re on My Mind,” with its intimate recollections of the South: “I think I smell the honeysuckle vine / The heavy sweetness like to make me sick / And the dogs, my God, they’re hungry all the time / And the snakes are sleeping where the weeds are thick / Mississippi you’re on my mind.”
Mr. Winchester was likened to other singer-songwriters of the era, including James Taylor, Jackson Browne and Gordon Lightfoot, but his life in exile — an American living in Canada but not really belonging to either place — hindered his career.
On Jan. 21, 1977, on his first day as president, Jimmy Carter pardoned U.S. citizens who had fled the country to avoid the draft. Mr. Winchester had a triumphant tour that stretched from Vermont to Hawaii, but he later retreated from the spotlight. He recorded sporadically and eventually stopped performing altogether, while continuing to write songs, including “O What a Thrill,” which became a hit for the country group the Mavericks in 1994.
“Culturally, I’m a Southerner,” Mr. Winchester told the Ottawa Citizen in 2002. “I like Southern cooking and music, and I don’t think that’s ever going to change. . . . I don’t think you ever lose your ties with your home country. I don’t think you want to.”
James Ridout Winchester was born May 17, 1944, in Bossier City, La., and grew up in Mississippi and Memphis.
He came from an old Memphis family, and his father was a lawyer.
Mr. Winchester, who was known as Jimmy before adopting the stage name of Jesse, graduated in 1966 from Williams College in Williamstown, Mass., where he majored in German.
His first two marriages ended in divorce. Survivors include his wife, Cindy Duffy of Charlottesville; three children from his first marriage; two stepchildren; a brother; a sister; and five grandchildren.
After returning permanently to the United States in 2003, Mr. Winchester had something of a career revival, recording an album in 2009 (“Love Filling Station”) and performing throughout North America. He continued to perform until this year and has a new recording, “A Reasonable Amount of Trouble,” awaiting release.
In 2010, he gained recognition with new audiences after performing on a TV program with Costello and other younger musicians. He brought tears to the audience with a quiet tune of teenage years with the unlikely title of “Sham-a-Ling-Dong-Ding”: “The way we danced was not a dance, but more a long embrace / We held on to each other and we floated there in space.”
In 2011, when Mr. Winchester was gravely ill with esophageal cancer, Costello, Jimmy Buffett and other performers recorded a tribute album, “Quiet About It,” consisting entirely of Mr. Winchester’s compositions.
One of the songs on the album, sung by Allen Toussaint, is “I Wave Bye Bye,” one of Mr. Winchester’s most poignant songs evocations of lost love:
The sailing ship reminds me
Of a certain girl
Who left a certain dreamer
To sail into the world
I have very friendly post-cards
From very far away
But they just remind me
Of a certain day
I wave bye bye
I pray God speed
I wish lovely weather
And all the luck that you need.