The cause was bladder cancer, said his manager and agent, Keith Case.
Mr. Winchester began writing songs in Canada, where he had moved in 1967 to avoid being drafted during the Vietnam War. He did not expect to return to the United States. Yet songs like “Biloxi,” “The Brand New Tennessee Waltz” and “Yankee Lady” on his debut album, “Jesse Winchester,” released in 1970, delved tenderly into memories of the South he had left behind.
“The Brand New Tennessee Waltz,” which Mr. Winchester said was the first song he wrote, was recorded by, among others, Joan Baez, the Everly Brothers, Anne Murray and Patti Page, who had a huge hit in 1950 with “The Tennessee Waltz.”
His songs were rooted in country, soul and gospel, and they strove to stay plain-spoken and succinct, whether he was singing wryly about everyday life or musing on philosophy and faith. In 1989 he told Musician magazine, “You can always find a way to say things in fewer words.”
James Ridout Winchester was born on May 17, 1944, in Bossier City, La., to James Ridout Winchester and the former Frances Manire. His father was stationed at Barksdale Field, an Army Air Corps base at the time. The family moved to a farm in Mississippi and later to Memphis. Mr. Winchester had 10 years of piano lessons, played organ in church and picked up guitar after hearing rockabilly, blues and gospel on Memphis radio.
He attended Williams College, where he majored in German, and enrolled for a year at the University of Munich, although he spent most of his time in Germany playing with a traveling rock band. Shortly after graduating from Williams, he received a draft notice and left for Montreal. “I didn’t see going to a war I didn’t believe was just, or dying for it,“ he said in an interview with No Depression magazine.
In Quebec he worked with bar bands and started playing the coffeehouse circuit, where he became a songwriter. “They expected you to write your own songs,” he told the online magazine Crawdaddy, “so I did.”
After a friend introduced him to Robbie Robertson of the Band, Mr. Winchester was signed by the Band’s manager, Albert Grossman. His debut album was produced by Mr. Robertson and received admiring reviews.
Sales were modest, partly because Mr. Winchester could not tour the United States to promote it. But “Yankee Lady” was a hit in Canada for Mr. Winchester, and later in the United States for Brewer & Shipley, and “Biloxi” became a staple of Jimmy Buffett’s repertoire.
Mr. Winchester released albums steadily through 1981 on Mr. Grossman’s label, Bearsville. The pensive, sparsely produced “Third Down, 110 to Go” — Canadian football has a 110-yard field — appeared in 1972; it included “Isn’t That So,” a bluesy song about God’s intentions and human temptations that was later recorded by Wilson Pickett. “Learn to Love It,” released in 1974, included “Tell Me Why You Like Roosevelt,” a 1940s song Mr. Winchester updated to praise Canada; in it, he recalled himself in 1967, singing, “The call to bloody glory came and I would not raise my hand.” In 1976, Mr. Winchester released “Let the Rough Side Drag,” which pondered love, faith and commitment.
Three months after President Jimmy Carter issued an amnesty for draft evaders in January 1977, Mr. Winchester, who had become a Canadian citizen in 1973, played his first United States concerts in a decade. He was ambivalent about the newfound attention. “It doesn’t seem fair to turn your back on your country and then come back when the coast is clear and make money,” he told Rolling Stone in 1977.
With the amnesty, Mr. Winchester could record again in the United States, although he continued to live in Quebec. He worked in Nashville with Emmylou Harris’s longtime producer, Brian Ahern, on “Nothing but a Breeze“ (1977); with another leading country producer, Norbert Putnam, on “A Touch on the Rainy Side“ (1978); and in Memphis with Al Green’s producer, Willie Mitchell, on “Talk Memphis” (1981).
Those albums gave Mr. Winchester his first presence on the American country and pop singles charts, but sales remained low, and longtime fans missed the sorrowful undertow of his earlier songs.
“Talk Memphis” was Mr. Winchester’s last major-label album. He would record infrequently through the following decades, though he continued to tour and write. He built a home studio, and royalties supported him as his songs appeared on albums by Wynonna Judd, Reba McEntire, Emmylou Harris, Jimmy Buffett and many others.
“I took stock and thought, ‘The only thing making money for me in this business is songwriting,’ ” he told one interviewer. “I don’t make any from records, and what little I did make from performing wasn’t usually worth the aggravation.” But in later years, he grew happier with performing, and he continued to tour into 2014.
Mr. Winchester made two country-pop albums for the Sugar Hill label, “Humour Me” in 1988 and “Gentleman of Leisure” in 1999.
In 2002 he married Cindy Duffy and moved back to the United States, settling in Charlottesville. He credited her “nagging” with getting him to record his last album, the 1950s-flavored “Love Filling Station” (Appleseed), in 2009. He had recently completed another album, “A Reasonable Amount of Trouble.”
Mr. Winchester’s first marriage ended in divorce. In addition to Ms. Duffy, survivors include a daughter, Alice Winchester; two sons, James and Marcus Lee Winchester; a stepdaughter, Jennifer Slangerup; three grandchildren; two step-grandchildren; a brother, Cassius; and a sister, Ellyn Weeks.
He learned he had esophageal cancer in 2011 and canceled a tour, but after surgery, he was pronounced cancer-free and returned to performing. In February of this year, he was found to have bladder cancer.
A 2012 tribute album, “Quiet About It,” included performances of his songs by Elvis Costello, Jimmy Buffett, James Taylor, Lyle Lovett, Emmylou Harris, Rosanne Cash, Lucinda Williams and Allen Toussaint.