The sound of the South has resonated in Jesse Winchester’s music, from his first recording in 1970 to his most recent 1999 release. Sometimes it’s through explicit geographical references such as "Biloxi" or "Talk Memphis," on others it’s in the background of R&B grooves on "Sweet Little Shoe" or the taste of gospel in "That’s What Makes You Strong." That feeling for place is perhaps part of the reason respected folk and country artists, including Reba McEntire, Emmylou Harris, Michael Martin Murphey, Mollie O’Brien, and Chris Smither, have chosen to record his songs.
"I still consider myself culturally a Southerner," said Winchester, who has lived in Canada since 1967. "I love the emotionalism of Southerners. Northerners seem to be more intellectual somehow, and Southerners are more from the heart. I like that. I like sentimental things, romantic things, and I think that affects my music. I still prefer Southern cooking," he added, "and I still say y’all to people."
He was born in Louisiana and spent his early childhood on his father’s farms in Mississippi and Tennessee. Though Winchester’s father, James, was expected to join the family law firm after he finished military service, he decided to work the land instead. "He was a hippie 25 years before his time," Winchester remarked in a 1994 interview. When Winchester was a young teenager, his father had to give up the heavy labor of farm work and moved his family to Memphis. The young Winchester loved the sounds that were coming over the radio, "R&B, country, and gospel," he recalled. "I listened to the same things everybody else in my age group, in the place where I lived, was listening to. And I loved all of it."
The Winchesters traditionally made careers in the military and in law, so Jesse did not grow up planning to play music for a living, although he did study piano and taught himself to play guitar. "I studied piano all through grade school and high school, and I was always in a band with my friends, and I played the organ in church, so I had a bit of formal music education," he said. "They taught me how to read music, and theory, and things like that." But he didn’t have a major career plan. "I really don’t know what I was thinking, just putting one foot in front of the other, you know. At the beginning of every school year my father would say it’s fine for you to take music lessons, but I don’t want you ever to become a professional musician. I just said, ‘Yeah, yeah — no problem,’ " he reflected, " but really, looking back, I always wanted to play guitar in an R&B band. And that did sort of come true eventually."
Winchester went on to study philosophy in New England and in Germany after high school, and then returned to Memphis where he got a job playing piano in a cocktail lounge while he considered his career direction. Then his draft notice came. It was 1967 and the height of the Vietnam era, and Winchester decided to move to Canada rather than serve in the war.
"I looked in the encyclopedia under Canada," he told Colin Escott in an interview for the liner notes of the reissue of his first album, Jesse Winchester, in 1994. "It said that Montreal was the largest city in Canada, which it was then, and the second largest French speaking city in the world. I had been in Europe for a while, and I liked living with a different language, so that appealed to me. That’s how clumsy my reasoning was."
