Jesse Winchester never set out to be a songwriter. When he was awarded an ASCAP Lifetime Achievement Award for his work in 2007, he was surprised and flattered. “I can’t account for it,” he says with his slight Southern drawl. “It’s the first time I’ve gotten an award, and I enjoyed it thoroughly. When I started out playing guitar, I never thought about being a songwriter. I wanted to be like Steve Cropper, a guitar player in an R&B band with good enough chops to make the singer I was backing up sound good.”

Winchester’s eponymous first album, released in the US on the tiny Ampex label in 1970, came out of nowhere, and included three of his much-covered signature tunes: “Yankee Lady”, a hit for Brewer and Shipley, “The Brand New Tennessee Waltz”, covered by Joan Baez and Patti Page, and “Biloxi”, which became a Jimmy Buffett concert staple. Jesse Winchester was produced by Robbie Robertson, which gave the songwriter immediate cachet and made him as famous for resisting the draft as for his music. (Winchester moved to Canada in 1967 to avoid the Vietnam war, but more on that later.)

The record was praised for Winchester’s laid-back vocals, gorgeous melodies, and insightful lyrics. His low-key style blended soul, rockabilly, gospel, folk, R&B, and a hint of Latin music that was perfect for the dawning era of pop singer-songwriters. He’s released 10 albums since then, including his current offering, Love Filling Station (Appleseed), but his reputation as a songwriter is assured. In the ’90s, he began pitching tunes to country artists and scored with “You Remember Me”, which Reba McEntire included on her multi-platinum album, Rumor Has It, in 1990, “Let’s Make a Baby King”, which Wynonna Judd cut on Tell My Why in 1993, and “O What a Thrill”, a hit for the Mavericks in 1994. He didn’t like touring, so the royalties allowed him to live comfortably and write the kind of songs he wanted to write.

Winchester, who is not related to the man who invented the famous rifle, grew up in the South on a series of farms in Mississippi, “but I never chopped cotton,” he says. “I tended to the cows now and then, but I had a comfortable, middle-class life. My first musical training was 10 years of piano lessons, which I’m glad I had, because I learned theory and how to read music, but I didn’t enjoy them. Later—when I listened to Ray Charles and Chuck Berry on the radio—is when the music started to click. When I heard ‘What’d I Say’ for the first time, I couldn’t believe it. How could somebody make music that made me feel so good? I had heard black gospel music, because all our neighbors were black, but [‘What’d I Say’] was far from anything I’d heard in church. It was an epiphany.”

Winchester’s teen years were spent in Memphis. He grew up playing organ in a Roman Catholic Church, and was familiar with gospel music, but says the hint of gospel in his own songs comes more from rock ‘n’ roll radio than from the church. “I wish the Catholics would get over themselves and adopt the Baptist songbook, or at least go back to Gregorian chant, which is beautiful. I’d go to church every day of the week if the music was that good. The gospel I picked up was from listening to Dewey Phillips over WHBQ in Memphis. He had a show called “Red, Hot and Blue” and was one of the first DJs to play white and black music without distinction. He’d play rhythm and blues, country music, boogie-woogie, gospel, and jazz and had an audience of white and black kids. I was young, but it made an impact.

“I kept up my straight musical activities in high school and played in rock bands. It never occurred to me to write songs, although I do remember looking at the labels of Elvis’ records and noticing there was a name under the songs in parentheses. A guy named Otis Blackwell. I’m sure if he’d come in the door, no one would have known him, but seeing his name under ‘Don’t Be Cruel’, ‘All Shook Up’, and ‘Great Balls of Fire’ impressed me.”

Winchester studied English and philosophy in college and spent a year in Europe to study German. “I’m not a great student or a scholar,” Winchester says thoughtfully. “I stayed in school to stay out of Vietnam and I had to pick a major, and although I’d taken a lot of French, German fascinated me. I was just wandering around academically; I didn’t know what the heck I was doing. The German I did learn I picked up playing in a German R&B cover band called the Night Sounds. I played electric lead guitar. I was the only American in the band. If I’d only gone to school, I never would have learned the language. We played for a while in France, where I became a big fan of [Charles] Aznavour and [Edith] Piaf, but I didn’t learn how to speak French properly until I played in a bar band in Quebec.”

Winchester landed in Quebec after he left the US in 1967 to avoid the Army and the jungles of Vietnam. For many years, he was most famous as a draft resister, and even today, most articles about him usually lean heavily on his “draft dodger” past. When asked if he’s tired of being grilled about the ’60s and Vietnam, he laughs. “Journalists have to have a hook to hang their story on, that’s natural. If I hadn’t left the country back then, I’d only be another guy with a guitar, so I understand. I’ve made my bed and I’m happy to lie in it. I was so mad about [Vietnam] back then; I could hardly talk about it. Since I’m not a pacifist, I couldn’t use that argument with the draft board, so I left the country.” When Winchester left, there was no organization of draft resisters, so his journey was undertaken on his own. “My dad was already dead, so I told my mother and consulted with an old family friend before I left, but I was on my own.

“To get landed immigrant status, you had to have a job offer and playing in a band wouldn’t fit the bill. I looked for a job as a journalist, but my French wasn’t good enough. There was a loose support system [for draft resisters] taking shape in Montreal and someone found me a professor who gave me a faux job teaching German. He was a complete stranger to me, but still lent me 500 dollars in cash to carry across the border to prove I had money. The conservatives have the idea that the hippies and youth were all about self-gratification—sex and drugs and rock ‘n’ roll—but the people then were very moral and principled and had a strong sense of right and wrong. That professor told me that one day I’d pass on my good fortune to someone else. The faith people had back then was kind of amazing.”

After landing in Montreal, Winchester played in various R&B cover bands and toured heavily, making good money when he actually got paid. The singer-songwriter movement took off in 1969 and he found he could get gigs closer to home in coffeehouses with just his acoustic guitar. “The money was good, you actually got paid, and they expected you to write your own songs, so I did. Up to that point, I’d never thought about writing songs, but I did and I produced ’em a lot quicker than I do now. But to be fair, there was a lot of dross in my work. I have drawers of dross.”

Winchester’s work was part of a big shift in popular music, moving away from commercial entertainment and toward a more honest mode of self-expression, but he hesitates to define himself as an artist with a capital A. “There is a difference between what I do and what came before, but I’m not sure how accurate my self-knowledge is. I like to think I’m on the entertainment end of the spectrum. First, you have to entertain; if something deeper is there for those who want to dig, that’s fine. But if you don’t entertain them, then you’r
e wasting everybody’s time, including your own.”

Until recently, Winchester considered his albums glorified demos. “I’m a very, very strict editor,” he explains. “I sing things over and over again before I record them and keep removing stuff. The process is kinda long and how it works for me, I just don’t know. Making records isn’t my strong suit. I’m a better live entertainer than a recording artist, and while I used to find touring aggravating, I’m getting better at it.