April 11, 2014 – James Ridout “Jesse” Winchester was born in Bossier City, Louisiana on May 17th 1944. He had 10 years of piano lessons, played organ in church and picked up guitar after hearing rockabilly, blues and gospel on Memphis radio.
During the height of the Vietnam War in 1967 he moved to Canada, where he began his career as a solo artist. After he became a Canadian citizen in 1973, he gained amnesty in the U.S. in 1977, but did not resettle there until 2002.
Winchester was born at Barksdale Army Air Field and raised in northern Mississippi and Memphis, Tennessee, where he graduated from Christian Brothers High School in 1962 as a merit finalist, a National Honor Society member and the salutatorian of his class. He graduated from Williams College, in Williamstown, Massachusetts, in 1966. Upon receiving his draft notice the following year, Winchester moved to Montreal, Canada, to avoid military service. “I was so offended by someone’s coming up to me and presuming to tell me who I should kill and what my life was worth,” he told Rolling Stone magazine in 1977. “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, expressing a viewpoint most intelligent people harbored.
Winchester began playing guitar in bands while still in high school. He played in Germany during college study abroad and after graduation. Upon arriving in Quebec in 1967, he joined a local band, Les Astronautes. He also began writing songs, which he performed as a solo artist at the Montreal Folk Workshop and at coffeehouses throughout eastern Canada, adding impetus to a revival in folk music that was taking place across Canada. 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 Robbie 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 Winchester, and later in the United States for Brewer & Shipley, and “Biloxi” became a staple of Jimmy Buffett’s repertoire.
His highest charting recordings were of his own tunes, “Yankee Lady” in 1970 and “Say What” in 1981. Probably best known as a songwriter, with his works being recorded by many notable artists, including Patti Page, Elvis Costello, Jimmy Buffett, Joan Baez, Anne Murray, Reba McEntire, The Everly Brothers and Emmylou Harris. His song “I’m gonna Miss You Girl” performed by Michael Martin Murphey from 1987 is probably best known. Many of these recordings have had success on various rock, folk and country charts.
“The Brand New Tennessee Waltz,” which 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.”
In 2002, he moved back to the United States, settling in Virginia. That year, his song “Step by Step”, from the album Let the Rough Side Drag, was used as background music for the montage that ended the first season of the television program The Wire. He received a Lifetime Achievement Award from the American Society of Composers, Authors and Publishers in 2007. Winchester continued to record and perform throughout the United States and Canada, releasing his tenth studio album, Love Filling Station, in 2009.
In 2011, Winchester was diagnosed with cancer of the esophagus and underwent treatment for the next couple of months. He was later given a clean bill of health from his doctor and resumed touring, but in April 2014, it was revealed that Jesse Winchester was “gravely ill” and receiving hospice care at his home, in Charlottesville, Virginia. He died there on the morning of April 11, 2014, aged 69, from bladder cancer.
Winchester’s final CD, A Reasonable Amount of Trouble, was released in September 2014, with liner notes by his friend Jimmy Buffett. Rolling Stone called it “a gentle collection of playful songs about love, memory and gratitude that amounts to one of the most moving, triumphant albums of Winchester’s 45 year career.