The Tennessee Kid

From the book Freedom Fighters and Hell Raisers: A Gallery of Memorable Southerners by Hal Crowther. Copyright © 2018 by Hal Crowther. Reprinted by permission of Blair.

Photographs can mislead, and sometimes conceal more than they reveal. But on occasion, usually in hindsight, a photograph radiates so much insight you need sunglasses to examine it. A photograph in my college yearbook, circa 1962, shows a bunch of mugging freshmen engaged in the lame freshman humor that coat-and-tie group portraits traditionally provoked. Two turkeys in the back row are holding up a sign pilfered from a diner somewhere: “One Golden Brown Juicy Breast—with all the trimmings—89 cents.”

Standing next to them, his torso half obscured by the juicy breast sign and a very strained look on his face, is a freshman from Memphis named James Ridout Winchester. You have to look carefully to confirm what you know for sure in hindsight, that it isn’t Jimmy Winchester’s hand holding up the left end of the breast sign. His hands appear to be deep in his pockets, and the sick look on his face says clearly, “Who are these people, and where am I, and why?” And this was in September, long before one of the six-month Siberian winters that drove more than one Southerner to transfer to Tulane.

It might be an understatement to say that Winchester was never comfortable at Williams College. Though a good fraternity welcomed him—he was a Tennessee thoroughbred with a pedigree that included Robert E. Lee—classmates never saw much of Jimmy. He was up in Bennington entertaining bohemian girls with blues chords, or he was on the road with his band, or rehearsing a rockabilly combo deep in the basement of the student union (if you sat quietly in the snack bar, you could just feel the beat). He lived off-campus with a divorced woman. Four years later, Winchester’s senior yearbook photograph shows much longer hair and a still-quizzical expression. Beneath it, no honors or activities are listed, though one of the class musicians Jimmy used to play with listed a band called Roget and the Mojo Teeth.

Winchester wasn’t the only one who experienced alienation in the Berkshire Mountains of New England. My hillbilly homesickness yielded slightly to an appetite for dead poets and distilled spirits, not necessarily in that order. From the beginning it was music that enabled Winchester to water his roots and endure his exile. He was from Memphis—a major South Memphis thoroughfare is Winchester Road— and most of us lacked the musical sophistication to grasp a fraction of what that implied. Elvis to be sure, but also Beale Street, B. B. King, Bobby Blue Bland, Sam Phillips and Sun Records, Booker T and the MGs. W. C. Handy was still living in Memphis when Jim Winchester was a teenager. When Handy died in 1958, Winchester’s grandfather spoke at his funeral.

It was an unfair advantage. Where I grew up, live music was Salty Austin and the Allegheny Ridgerunners, aping Porter Wagoner. On weekdays Salty sold Electrolux vacuum cleaners door-to-door and left personalized guitar picks instead of calling cards. Once a month at American Legion Post 808, an emaciated, Baptist-looking woman named Audrey performed standards on the Hammond organ, backed up by her husband Pike, who looked anesthetized and played the drums with brushes. The culture gap between Sam Phillips and the Audrey/Pike ensemble might account for the discrepancy between Winchester’s musical achievements and my own. But probably not.

“My mother tells me music was always my focus,” Winchester recalled in 1999. “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. But really, looking back, I always wanted to play guitar in an R&B band.”

Going his own way, Winchester became a man of mystery at the college, the kind classmates tend to mythologize. I remember the rumors that he was in Boston or Springfield most weekends, opening shows for Taj Mahal. But a year out of Williams, after graduate study in Germany and a summer playing lounge piano in Memphis, Winchester took his myth to another level. His Vietnam draft notice came and he decamped for Montreal, guitar in hand—the only draft resister in the class, to my knowledge, who took the high road of emigration and public opposition to the war. The “Tennessee kid,” as he calls himself in the classic “Brand New Tennessee Waltz,” had committed himself to an exile that was neither academic nor symbolic.

“I was so young and naïve that it wasn’t that difficult a decision,” he said later. “I just wasn’t thinking very far into the future.”

The alumni grapevine works fast those first few years out of school. Winchester’s departure was much discussed in New York. Most of us admired him for it. A couple of years after he moved to Montreal, a postcard of sorts arrived, a here’s-how-I’m-doing that was characteristically original and myth-enriching. Jim was “Jesse Winchester” now, and that was the name of his debut album on the Bearsville label, produced by Robbie Robertson of The Band. “Jesse Winchester” introduced “The Brand New Tennessee Waltz,” “Yankee Lady,” and “Biloxi,” three of the prettiest, subtlest, most mind-adhesive songs in the country-rock canon. They’ve been covered by so many singers that to this day they cover his alimony payments, as Jesse once told me mournfully.

The album photographs revealed that Jesse had a beard now and a lot more hair—quite a few of us had acquired beaucoup hair in the four years since graduation. He looked like a prophet; he had Robbie Robertson, Garth Hudson, and Levon Helm for sidemen on his album; he knew Bob Dylan and Leonard Cohen. While his fraternity brothers were trying to pass their orals or make junior partner—while I was reviewing TV shows—Jesse was an international fugitive and a Canadian celebrity. He was light years ahead of the pack. And his songs were grand, to my ear—lyrical, ironic, simultaneously self-illuminating and self-deprecating. Smart, and full of displaced-Southerner angst.

“Now you know what they say about snowflakes,” he mourns in “Snow,” as another iron winter closes in. “How there ain’t no two the same? Well, all them flakes look alike to me. Every one is a dirty shame.”

“Jesse Winchester” backed up a wistful personal narrative with everything a boy soaked up in Memphis—blues, R&B, gospel, country, rock and rockabilly. Critics were uniformly impressed; performers and industry professionals were enthusiastic.

“As a collection of songs, the album is still nearly without peer,” Herb Bowie wrote in an online review of Jesse’s recordings, thirty-four years later.

“There was an intimacy in those songs that was new,” recalls Barry Poss of Sugar Hill Records, which released two later Winchester albums (Humor Me in 1988 and Gentleman of Leisure in 1999). “It was a whole different take on love and loss.”

“What my songs seem mainly to focus on is relationships with women or relationships with God,” Winchester told an interviewer. “I tend to get those two confused.”

Schoolmates who barely knew Jesse at Williams were suddenly his disciples. If his albums made small waves in the music industry, they made big ones in the class of ’66. It’s hard to invest much in the celebrity of adults we knew when they were children; we know them too well to buy into the mystique. But the separateness that Jesse always maintained— that was his trademark—allowed us to be his fans. There was a strange meeting in the late ’70s that I always recall when I reflect on the paradox of celebrity. I went to hear Jesse play at The Pier in Raleigh, in the company of his old fraternity brother Bill Bennett, who was later to become Secretary of Education and federal drug czar under Ronald Reagan—and eventually the self-appointed guardian of America’s morals, until a hemorrhaging addiction to high-stakes gambling cost him his pulpit.

Bennett, too, is a great character, of a less endearing variety. The three of us sat backstage after Jesse’s show, in a tiny dressing room that reeked of cigarettes, making awkward small talk about undergraduate adventures. Bennett and I were unconditionally impressed with Winchester; for his part he was impeccably gracious but seemed to find us almost as bewildering as those freshmen with the juicy breast sign in 1962. Bennett and I were both becoming pontificators—of radically different types, I hope—and Jesse was an artist born, a different animal. I know what I think of Bennett; I’m fairly sure I know what Winchester thought of him, too. I had no idea what Jesse thought of me.

There’s a distinct male pecking order where musicians rule; you’re tone-deaf if you think William Bennett, who once aspired to the presidency of the United States, was the celebrity in that little room. Bennett himself would never make that claim. Like me, like the rest of us, he probably followed the rest of Jesse’s career as avidly as Memphis kids followed Elvis.

It’s been an uneven, almost unclassifiable career. Winchester became a Canadian citizen in 1973. When Jimmy Carter pardoned the Vietnam draft resisters in 1977, a friend called Jesse in Canada, and he remembers that he “just sat down on the bed and wept, I was so moved.” But he kept faith with the Maple Leaf, with the country that welcomed him when America had no peaceful use for him. He lived most of his adult life in Quebec and raised three children there, for years in the Eastern Townships, seventy hard winter miles from Montreal.

Though no less an authority than Bob Dylan calls him one of the best singer-songwriters of his generation—Dylan’s generation—the conventional wisdom is that exile deprived Jesse of a chance to be a star.

“His early inability to tour in the U.S. may have permanently stunted his commercial success,” speculated Herb Bowie. Jesse’s stock never traded briskly on the celebrity exchange; People magazine, a founder of that grim exchange, said of Winchester in February of 1989, “He certainly seems too obscure for a performer of his talent.”

In 1990 Jesse announced his retirement as a performer and recorded nothing for a decade. When he returned in 1999 with Sugar Hill’s Gentleman of Leisure, his obscurity had become a theme. In a piece headed “The Return of Jesse Winchester” in the Toronto Star, Nick Krewen described an artist “whose stature, through ten albums and 28 years has always been more satellite than star, orbiting the peripheral [sic] between respectability and reverence.”

“Album sales have been nominal,” Krewen added.

Jesse himself made black humor of his meager renown, with a streak of self-mockery prefigured by his second album, Third Down, 110 to Go. He recalled opening for Jimmy Buffett and singing one of his own songs that Buffett had recorded. “The audience was annoyed because they thought I was singing one of Jimmy’s songs,” he said. “It’s kind of the story of my life.”

The image industry isn’t everything—in an age of Britney Spears, Donald Trump, and American Idol it’s a pretty dismal business. While his career appeared to languish, Winchester’s songs were recorded by a formidable lineup of discriminating A-list artists including Joan Baez, the Everly Brothers, Waylon Jennings, Bonnie Raitt, Emmylou Harris, Reba McEntire, Elvis Costello and Wynonna Judd. The attention dried up but not the money. Unlike some great blues artists who had more lean years than fat, Winchester never had to load trucks or play lodge picnics to make ends meet. But he became one of those cult figures who separates serious music buffs from the day-trippers. Everyone knowledgeable knew who he was, but almost no one knew where he was.

By paying close attention I managed several Winchester sightings over the years, every one rewarding. One night in the mid-’80s my wife and I caught up with him at Rhythm Alley in Chapel Hill, North Carolina, for a set highlighted by a remarkable live version of Jesse’s funky “Rhumba Man.” (“My step might be old-fashioned/But it’s just fine with me/I got a couple of rhumba steps/You might like to see.”)

Here was a skinny, incongruously formal guy with a neatly trimmed beard, dressed like an off-duty librarian, performing a weird soft-shoe shuffle like your Uncle Dan might assay after his third martini. But you quickly saw the art of it. No hoofer, no athlete, Winchester just had those Beale Street rhythms coiled around his bones, and his exhibition of fancy footwork was one of the most arresting novelties in show business. If you’re thinking Savion Glover, move along. If you love the Rabbit Dance performed by Too Slim Riders in the Sky—who also played Rhythm Alley—“Rhumba Man” live might have been your personal epiphany.

Backstage alone, reserved as always but with his Southern manners fine-tuned by the presence of a lady, Jesse seemed genuinely glad to see us. The last time I talked to him, he was working my favorite bluegrass festival, Doc Watson’s MerleFest in North Wilkesboro, North Carolina. With all the credentials he carried—Memphis, Montreal, Nashville, political dissent, the imprimatur of Dylan and The Band— you’d think Jesse might have worked up some kind of hip look for himself, at least onstage, at least surrounded by so many musicians in their righteous gear. Instead he performed in a V-neck sweater, striped button-down shirt, chinos, and penny loafers—a uniquely retro costume borrowed from a small-town history teacher, or one of our more conservative preppies at Williams long ago.

Graying now, playing alone on a vintage guitar, Jesse made our day—the few of us, the ones who knew—with a low-key set of familiar, beautifully crafted songs. Backstage he was abstracted, shy, a wayfaring stranger who didn’t seem to know anyone—still an exile, as he sang and wrote, “with my feet in Dixie and my head in the cool blue North.”

The class grapevine is fraying now; there are a lot of missing links in the network, one way or another. Classmates have died, of course; another one reached Jesse by e-mail to ask him if he might be interested in performing at the fortieth reunion of the class of 1966. The predictable answer was a polite but resounding “No thanks.” Not even Barry Poss, who recorded Jesse, could ever tell me exactly where to find him, though he knew people who might know, he said. The only clues were on Jesse’s website. Once it listed a three-show tour in Northern California—Petaluma (McNear’s Mystic Theater), Saratoga, Santa Cruz—that coincided exactly with a trip I made to Death Valley. But those east-west roads in the desert aren’t so good, and I felt way too old to drive across the Sierra Nevadas at night, even to see Jesse Winchester. There was no hurry, it seemed to me. The Rhumba Man was out there somewhere, and somewhere we’d meet again. I was wrong. In 2014 I got a call from a friend in New York, a classmate who had once played the drums in Jesse’s band. His news was that Winchester, back in the States since 2002, had died of cancer at his home in Charlottesville, just short of his seventieth birthday. I thought of some lines from “The Brand New Tennessee Waltz”: “Let all of your passionate violins play a tune for a Tennessee kid/Who’s thinking of leaving another town, with no place to go if he did/They’ll catch you wherever you’re hid.”

Hal Crowther is an award-winning critic, essayist, and journalist whose work has appeared in Time, Newsweek, Oxford American, Granta, and Narrative magazines. He is the author of four essay collections and An Infuriating American: The Incendiary Arts of H.L. Mencken. His third essay collection, Gather at the River, was a finalist for the National Book Critics Circle prize for criticism. He lives in Hillsborough, North Carolina, with his wife, novelist Lee Smith.

There are 2 comments for this article
  1. Robert McGuill at 7:25 pm

    Wonderful piece, Mr. Crowther. Fell in love with Winchester’s music when I was freshman in high school back in Maryland. Still have all his vinyl. Got to see him in concert here in Colorado at the Colorado Springs Fine Arts Center a couple of years before he died. What a light. What a talent. Thanks for catching us up.

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