Born in 1944, by the time Jesse Winchester attended Williams College in Williamstown, Massachusetts on a music scholarship in the mid 1960s, the Louisiana native had spent his childhood around the state living on small farms, then moved to Memphis with his family at the age of 12, after his father had suffered a heart attack.
Listening to the R&B, gospel, and country sounds that filled the airwaves, he spent his high school years playing in a number of makeshift groups, and became an accomplished guitarist, vocalist, and pianist. But while in college he switched his major to study the German language, and spent a year in Munich before returning to the US to continue his studies in ’66.
Opposed to America’s involvement in the Vietnam War, he moved to Montreal a year later to avoid the draft, and shortly after joined an up and coming folk group called Les Astronauts as their guitar player. Within a year he chose to go solo, and quickly became a staple on the local coffeehouse circuit. His scope broadened, as did his audiences, and he conquered that market as well before the end of the decade.
While performing in Yorkville in early 1970, Robbie Robertson caught one of his performances, who helped get him a recording deal with Ampex, and produced his self-titled debut album later that year. A young Todd Rundgren served as engineer on the record, which featured a host of session musicians that included Robertson’s Band-mate Levon Helm on drums and mandolin, Al Cherney on fiddle, Bob Boucher on bass, Gord Fleming on piano, and Robertson and David Rea on guitars.
The album featured all original and self-written songs, with the exception of “Snow,” which he co-wrote with Robertson, one of the three singles released over the next year. Along with the others, “Yankee Lady” and “Quiet About It,” it did well on the charts while the album made it to #26, fuelling a cross-country tour.
He found a new home on Bearsville Records and showed he’d embraced his new home country with the football-based entitled THIRD DOWN, 110 TO GO in 1972. Co-produced by Rundgren, it again featured a plethora of guest musicians, including Fleming again on piano and Boucher on bass, as well as Amos Garrett on guitars. Recorded at Les Studios in Montreal, and Toronto’s Eastern Sound, it continued on the folk/country path with the single “Isn’t That So,” which found its way onto Canada’s top 40 list.
But despite huge critical acclaim, his inability to tour in the U.S. it’s widely a critic’s opinion that this prevented him from taking his place among the major singer/songwriters of the early ’70s. Still, Winchester was a live favourite, despite becoming notorious for being low-key with his live performances, and only toured briefly with a handful of live dates to promote the album.
With Russell Smith, David ‘Butch’ McDade and Jeff ‘Stick’ Davis, he formed a backing group called The Rhythm Aces, and after becoming a Canadian citizen in 1973, he released LEARN TO LOVE IT the following year. By this point he’d become a regular performer at the Hotel Le Chatelet in Morin Heights, Quebec, run by several Tennesseans who had moved there a couple of years earlier. Stripped down with Garrett returning as one of the few guest musicians, it contained the top 40 hits “L’aire de la Louisiane” and “Third Rate Romance,” penned by Smith. After his backup group left a year later, they recorded it themselves and again took it to the top 40 as The Amazing Rhythm Aces. The album also featured a pair of other non-original songs – “The End Is Not In Sight” (also penned by Russell Smith) and a cover of Martha Carson’s “I Can’t Stand Up Alone.” On the album, Winchester also vented his penned-up political frustrations with “Tell Me Why You Like Roosevelt.”
Getting back to a fuller sound, he released LET THE ROUGH SIDE DRAG in 1976. The title track became the first of three singles, and was the b-side when the label decided to re-release “The Brand New Tennessee Waltz” from his 1970 debut as the second single, followed by “Everybody Knows But Me.”
But because of his decision to leave the US to avoid the draft, he’d been unable to tour there, which changed when President Jimmy Carter granted amnesty to draft dodgers. Although it was originally only for those who hadn’t deserted the Army or had become citizens of another country, Winchester’s manager Barry Bozeman was able to convince Carter to broaden the scope of the amnesty. He made his first appearance back in the US that year on April 21, for a sold out performance in Burlington Vermont. Rolling Stone magazine covered the event, coining the phrase “the Greatest Voice of the Decade” to describe Winchester’s vocal style.
He turned to producer Brian Ahern for NOTHING BUT A BREEZE in ’77, which would become his most commercially successful album. It was certified gold on the backs of the singles “Rhumba Man,” “Pourquoi M’aimes-tu Pas?,” and the title track. Other noteable cuts included the song about finding your bag of pot almost empty and no way to replenish it called “Twigs & Seeds,” and the soulful “Bowling Green.”
Experimenting with a broader sound than ever before, 1978’s A TOUCH ON THE RAINY SIDE featured strings and a complete horn section on several of the tracks, as well as congas, harmonicas, and various keyboards arrangements, producing the singles “Sassy” and “Wintery Feeling.” Produced by Norbert Putnam and generally regarded by the critics as one of the best roots albums of the ’70s, it also featured the cover of Irwin Levin and Toni Wine’s “Candida,” the groove-ridden “Step By Step,” and “Little Glass of Wine.”
He called upon Willie Mitchell, one of R&B’s most sought after producers for his next project. Recorded at Mitchell’s Royal Recording Studio in Memphis, Tennessee, the aptly titled TALK MEMPHIS had a definite southern feel with a well-rounded sound, with the title track and the singles “Say What” and “Baby Blue.” By this point his penchant for touring less and less had almost ground to a complete hault, and he retreated from the business all together.
Throughout the rest of the decade he took to the stage only a handful of times, and didn’t return to the studio at all until 1989. After a greatest hits package earlier that year, he found a new home with Sugar Hill Records, and released HUMOUR ME. Critics quickly rejoiced at the singles, the melancholy folk ballad, “I Want to Mean Something to You” and the infectiously grooved “Well-A-Wiggy,” as well as other tracks like the lead-off “If I Were Free,” “I Don’t Think I Love You Anymore,” and the title track. He set out on the road for a series of dates over the next year or so that took him across Canada and the US. As was customary by this point, he was accompanied by his guitar, and little else. He received his first Juno Award nomination in 1990 for Best Country Male Vocalist, though he lost out to George Fox.
He again slipped out of the limelight and only made the rare live appearances, usually at folk and root festivals. Produced by Jerry Douglas, the appropriately titled GENTLEMAN OF LEISURE marked his return a decade later, with his trademark gentle humour and poignant writing about everyday life, loves lost, and dreams unfilled. But always an artist who enjoys challenging himself and his limitations, “Club Manhattan” had an almost rockabilly feel, while “Sweet Little Shoe” travelled down a funky blues road, and “Sweet Loving Daddy” and “That’s What Makes You Strong” personify sentimentality. The album also marked a return to surrounding himself with a bevy of talent in the studio, including Vince Gill, The Fairfield Four, and Steve Cropper.
As the new millennium got under way, several of his albums were re-released in pairs on single CDs. He received a Lifetime Achievement Award from the American Society of Composers, Authors and Publishers in 2007. But with few stage performances in recent years and after a handful of live and studio compilations, it would be another decade before he returned with new material again.
Now on Appleseed Records, 2009’s LOVE FILLING STATION exemplified Winchester’s penchant for keeping his music simple, without any studio trickery and bare bones essentials. He’d moved back to the US earlier in the decade, settling in Virginia, and The Delta blues was prevalent in tracks like “O What A Thrill,” “Wear Me Out,” and “Bless You Foolish Heart.” Critics also praised his return to the simplicity of him and his acoustic guitar in the smooth, laid-back approach to the lounge styled “Sham-A-Lam Ding-Dong,” and the cover of the Ben E King standard “Stand By Me.”
In 2011, Winchester was diagnosed with cancer of the esophagus and had to undergo treatment for the next couple of months. Making a full recovery, he returned to performing live (usually as a solo artist), and also picked up his guitar and brought a few friends to record THE STORYTELLER LIVE that same year. Running the spectrum of his illustrious career, the album embraced a quiet intimacy one might expect from catching a favorite singer at a local club. Before the year was up, he appeared on Elvis Costello’s program “Spectacle,” where they shared the stage and stories with Sheryl Crow, Ron Sexmith, and Neko Case.
A year later, friends, artists, and colleagues collaborated on the album called QUET ABOUT IT – A TRIBUTE TO JESSE WINCHESTER. On the list were the likes of James Taylor covering “Payday,” Allen Toussaint’s version of “Gentleman of Leisure,” Little Feat doing “Rhumba Man,” and Elvis Costello’s version of “Quiet About It.”
Over the course of his career, Winchester became one of the industry’s most highly sought-after songwriters. His songs have been covered over the years by a wide range of artists, including Anne Murray (“Wintery Feeling”), Elvis Costello (“Payday”), Emmylou Harris (“Defying Gravity”), The Weathergirls (“Well-A-Wiggy”), Lyle Lovett (“Isn’t That So”), Tom Rush and Jimmy Buffett (“Biloxi”), Wynona Judd (“Let’s Make A Baby King”), Tim Hardin and Brewer & Shipley (“Yankee Lady”), Reba McEntire (“You Remember Me”), and The Everly Brothers, Joan Baez, and Patti Page (“Brand New Tennessee Waltz”), among many others.