Jesse Winchester was so talented a singer and songwriter that Bob Dylan said of him, “You can’t talk about the best songwriters and not include him.” His songs, overflowing with images and emotions from his own life, were recorded by singers such as Bonnie Raitt, Elvis Costello, Joan Baez, Jimmy Buffett, James Taylor and Emmylou Harris.
Mr. Winchester, a Louisiana native, moved to Montreal as a 23-year-old draft dodger in 1967, during the Vietnam War. He stayed for 35 years and became a Canadian citizen, and some of his family members still live here.
Many of his songs reflected his homesickness for the Deep South. He was born on May 17, 1944, in Shreveport, La., and spent his early years in Mississippi, where his father farmed. His song Biloxi told of a young boy playing on the beach on the Gulf of Mexico. His mother encouraged him to start playing piano when he was six. After his father had a heart attack and gave up farming, the family moved to Memphis when Jesse was 12. His father started a career as a lawyer, and Jesse bought his first guitar.
He once told an interviewer that his years in Memphis were the period when he learned to love black music, as did his friends: “It was raw, it was simple and it came from the heart.” They looked down on country music and Nashville; Memphis was more southern, Nashville more Appalachian and, they thought, “too white.”
Later he learned to appreciate country music. “Accepting country music also has a lot to do with accepting who you are and where you are from,” he told an interviewer. But Memphis remained his favourite city; while living in Quebec, he wrote a song called Talk Memphis, about the accent he loved and missed.
In Memphis, he and his friends played in local bands. His musical talent won him a scholarship to Williams College in Massachusetts. Along with music he studied German and spent a year studying in Munich, where he played with some local bar bands. Soon after graduating from Williams, he received his draft notice for military service.
Although he was proud of his father fighting in the Second World War, and was a distant relation of Confederate General Robert E. Lee, Mr. Winchester thought the Vietnam War was immoral. He moved to Montreal and was soon playing in coffee bars. Eventually Robbie Robertson of the Band discovered him and produced his first album, 1970’s Jesse Winchester.
Then began the most productive period of his life, as he recorded 10 albums in 19 years. Mr. Winchester made his life in Montreal, became a Canadian citizen in 1973 and learned French (he said speaking French made him feel “smart and creative”). But he missed his family and friends and sang about not being able to go home in one of his earliest songs, The Brand New Tennessee Waltz. Patti Page, who sold millions of copies of The Tennessee Waltz in 1950, recorded his Brand New Tennessee Waltz in 2000.
In 1977, then-president Jimmy Carter granted an amnesty to draft dodgers, but by then Mr. Winchester had decided to remain in Canada “When the amnesty happened I had already had 10 years of being a Canadian, raising a Canadian family. My life was in Montreal,” he told an interviewer years later.
Although he was prolific , he was not as successful as he might have been had he stayed in the United States. This led to depression, drinking and a marriage breakdown. He gave up performing but continued to write songs for others, including Rhumba Man, which made it to No. 3 for the late Nicolette Larson, who sang it as Rhumba Girl.
“The fear of performing never leaves you,” he once told The Globe and Mail. “But if you’re afraid, drinking is this crutch that actually works for a while. I had a drinking problem that was then greatly exacerbated by a terrible divorce. It left me pretty much mentally ill for a time. I found myself out on stage repeating myself – I felt like such a sham.”
In 2002 Mr. Winchester married Cindy Duffy, and moved back to the United States after spending more than half his life in Canada.
He recorded a new album in the late 1990s (Gentleman of Leisure) and started performing again. In 2007 he was awarded a lifetime achievement award from the American Society of Composers, Authors and Publishers. In 2010, he appeared at a Sundance music festival organized by Mr. Costello and was a hit performing his love ballad, Sham-A-Ling-Ding-Dong (from 2009’s Love’s Filling Station).
Mr. Winchester fell in love with his adopted country. In 1974 he wrote Tell Me Why You Like Roosevelt, adapted from an earlier song and sung in the style of a gospel singer, complete with background chorus. Although it praised the New Deal president, it was more about prime ministers Lester Pearson and Pierre Elliott Trudeau, who allowed American draft dodgers to enter Canada.
Mr. Winchester had surgery for cancer of the esophagus in 2011, and was diagnosed with bladder cancer in February of this year. He died on Friday at his home in Charlottesville, Va., at the age of 69.
He leaves his wife, Cindy; sons James and Marcus Lee; daughter Alice; step-daughter Jennifer Slangerup; three grandchildren and two step-grandchildren; brother Cassius; and sister Ellyn Weeks.
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