American singer-songwriter Jesse Winchester sadly passed away on April 11, 2014 at his home in Charlottesville, Virginia following several years battling cancer. He was 69. Jesse Winchester was a product of the South. He was one of those rare writers with the knack of writing timeless, seemingly American melodies that have the distinct flavour of his home region; a kind of wistful French charm blend with a lazy country life you would associate with a hot sticky climate. Yet surprisingly, Winchester, and much of his music, has been completely ignored by country music.

I first encountered his music back in 1970 via an import copy of his debut self-titled album. For months it was hardly off my turntable and has remained close at hand for the ensuing 40-odd years, albeit more recently via CD reissues. I’ve followed his music career diligently, and though he only released a dozen albums, each one is a genuine treasure … an unexpected surprise and an alloyed joy. Cult hero is an oft-misused term, but when it comes to Jesse Winchester, it is most apt.

Music history proves that some artists are simply too good to make it. Jesse Winchester is one of those artists and writers who never achieved the kind of commercial success that his talent deserved. Indeed, he probably never had a wish to become big and famous. A fine singer and songwriter whose economic and tasteful use of both melody and language is genuinely emotive and endlessly fresh, he has had his songs well-covered by such diverse artists as Emmylou Harris, Wilson Pickett, Reba McEntire, Jimmy Buffett, Joan Baez, Wynonna, John Denver, Ed Bruce, Elvis Costello, the Mavericks, Dan Seals and many, many more.

Jesse Winchester was born on an army base in Bossier City, Louisiana on May 17, 1944, where his father was stationed, although he moved with his family to Memphis when he was still young. His family had a strong church background, his great-grandfather was the Bishop of Arkansas and a cousin was the Bishop of Chicago. Like most kids in Memphis, Jesse grew up to the sound of r&b and country music. But the first music he played was more sedate. He took piano lessons, eventually finding himself in the school orchestra. He also played the organ at his local church. By the time he had reached his teens however, the music of the streets was demanding his attention. He played in a local rock’n’roll band, churning out reasonable facsimiles of the hits of the day.

Music, however, was still only a secondary interest in his life. He studied philosophy at universities in Massachusetts and Munich. This was the beginning of 1966 and whilst in Munich he joined a German band, playing rhythm guitar. With his studies completed, he then returned to Memphis and spent several months doing nothing more impressive than playing a piano in a bar. Then Jesse received his call-up papers for service in Vietnam. He decided that was not to be his immediate life, and on moral grounds, set about evading military serve, eventually seeking political asylum in Canada.

He chose Montreal simply because it is the second biggest French-speaking city in the world. He joined a French-Canadian bar band, then came an r&b band called the John Cold Water Group and a solo career as a singer-songwriter. He also immersed himself in his hobby of writing songs. Within six months he was working the bars by himself, covering a wide range of well-known songs and also featuring several of his own creations. While recording a demo tape of some of his original songs in Ottawa, he was introduced to Robbie Robertson of The Band, who was immediately impressed by the quality of Winchester’s work and introduced him to Albert Grossman, The Band’s manager, who signed Winchester to the short lived Ampex label.

The result was the album JESSE WINCHESTER, which, with the presence of people like Levon Helm and Robbie Robertson of The Band and fiddle player Al Cherny, conspired to turn Jesse into something of a cult figure, head—if not quite shoulders—above the competition. From the thigh-slapping rockabilly of Payday to the pathos of the loser’s tale of The Brand New Tennessee Waltz, Jesse’s touch was that of a master. Though it won media acclaim, the album sold poorly.

THIRD DOWN, 110 TO GO, named after a term used in Canadian football, followed two years later on Bearsville. Mainly produced by the singer, with three tracks rescued from an aborted Ampex album produced by rock guru Todd Rundgren. By this time Winchester was beginning to attract cover versions by Kenny Price, the Everly Brothers, Stoney Edwards, Delbert McClinton and Wilson Pickett. His third album, LEARN TO LOVE IT contained the original versions of Third Rate Romance and The End Is Not In Sight later hits for the Amazing Rhythm Aces, two of whom, Butch McDade and Jeff Davis, played on the album.

Jesse’s forced absence from the States encouraged a certain yearning quality in his writing. His Mississippi You’re On My Mind is the perfect, bittersweet example of this homesickness. His lyrics are fired by an almost schizophrenic nostalgia for the way of the old South. The cultural diversity of his background had been assimilated into his music, creating a vision of America that had also been shaped and refined by a sharp intelligence and an exile’s romanticism. Wake Me, for example, is based on the mood, tempo and call-and-answer structure of a spiritual, and Winchester encompasses blues and country of every sub-division with equal empathy.

His fourth album, LET THE ROUGH SIDE DRAG, from 1976, was streaked with the ambivalence you might expect from a keen patriot in self-imposed exile. Emerging as one of the great singer-songwriters of the 1970s, Jesse Winchester was up there alongside Carole King, James Taylor and Elton John. His songs have this timeless quality that gives the impression that they could have been written at any time in the past 300 years, and yet still have significance to listeners of today and in the future.

By this time, though, his album sales were still relatively disappointing, he was gaining lots of covers by Waylon Jennings, Nicolette Larsen, and country singer Stoney Edwards, who not only cut a superb version of Mississippi You’re On My Mind, but also My Songbird and had a unique affinity with Winchester’s songs. There's little doubt though that remaining in Canada had proved to be a hindrance to advancing his career in the States.

President Carter declared an amnesty for draft dodgers in 1977, but Jesse remained based in Canada, writing and recording great songs that solidified his critical acclaim and popularity among other artists. Jesse’s Rhumba Girl was a pop hit for Nicolette Larson, Well-a-Wiggy reached the r&b charts in a version by the Weather Girls, and Michael Martin Murphey had a top 10 country single with I’m Gonna Miss You, Girl.

His fifth album, 1977’s NOTHING BUT A BREEZE, was produced by Canadian Brian Ahern in Toronto. He brought in some big-hitters with Anne Murray, Emmylou Harris, Nicolette Larson and Herb Pedersen on background vocals plus James Burton, Ricky Skaggs and Glen D. Hardin from Harris’ Hot Band. By this time Jesse was able to work in America. So it was that A TOUCH ON THE RAINY SIDE was produced by Norbert Putnam in Nashville, but rather than a steel guitar-drenched country record, this was more of a deep south country-soul set with subtle horns alongside the funky arrangements. It was the perfect foil for such great songs as A Showman’s Life (revived by both George Strait and Buddy Miller), Wintry Feeling and Just Now It Feels So Right.
TALK MEMPHIS, his final album for Bearsville, is my least favourite. Produced by Willie Mitchell in Memphis, the city where Jesse grew up, the album had the desired effect as it produced a US hit single Say What in 1981. Don’t get me wrong, it’s a good album, probably not what I’d been expecting or had hoped for. Very southern soul in sound and there are some excellent Winchester originals; in particular Leslie is wonderfully evocative complete with a cool breeze shuffle rhythm and atmospheric keyboard and guitar.

By this time Jesse had become friendly with Jimmy Buffett, who had not only recorded several of his songs, such as Biloxi, but also invited Jesse out on the road to open shows for him. He nurtured good publishing relationships in Nashville and gained some worthwhile covers of his songs that more than sustained him and his family. Ed Bruce had a top 20 country hit with Evil Angel, Dan Seals recorded Sweet Little Shoe, and a little later Wynonna cut both Just Like New and Let’s Make A Baby King on her multi-platinum TELL ME WHY album.

After releasing seven albums between 1970 and 1981, Jesse took some time off to recharge, living on the royalties from his songs. He resurfaced in 1988 on Sugar Hill with HUMOUR ME, a superbly crafted collection of new songs in his time-honoured style. There’s a rootsy country feel throughout provided by such seasoned players as Sam Bush, Jerry Douglas, Béla Fleck, Edgar Meyer, and Mark O’Connor. But central to the album’s enticing vibe is Jesse’s songs that range from the light gospel flavoured Let’s Make a Baby King, to the gentle Love Is Fair and the r&b styled Well-A-Wiggy.

It was to be another ten years before Jesse released a second album for Sugar Hill. The aptly titled GENTLEMAN OF LEISURE was an instant reminder of what great music had been sadly missing from our lives. A leisured, predominantly acoustic set, it exudes confidence and charm. Several of the songs had been lying around for years. Evil Angel, first recorded way back in the early 1980s by Ed Bruce, is given a bluesy reading by the writer, with soulful harmonies by Jonell Mosser and producer Jerry Douglas. Sweet Little Shoe is another oldie. Previously recorded by Dan Seals, this is a funky little workout with great lead guitar by Mike Henderson.

Material runs the gamut from overtly spiritual tunes such as Wander My Way Home with the Fairfield Four adding those rich gospel tones, to the standard country feel of Sweet Loving Daddy. The song's not exactly a world-beater, but Jesse’s seldom sounded warmer. He was joined by Vince Gill on Just Cause I’m In Love With You, presenting a lovely mellow feel, but that’s okay; somehow Jesse Winchester always sounds like he’s sitting right next to you, singing a ballad just for you. Jerry Douglas surrounds his vocal with lightly rattling guitars, pillowy steel, a shuffling beat and irresistible harmonies.

In 2002, Jesse and his new wife finally relocated back to the States, in Virginia. While he has maintained an active touring schedule it was to be another seven years before he returned to the recording studio to record LOVE FILLING STATION, which was released on Appleseed in 2009. Again several of the songs had been lying around for years. I’m Gonna Miss You Girl was a top ten country hit for Michael Martin Murphey in 1988; O What A Thrill a top 20 country hit for the Mavericks in 1994. Jesse also selected three outside songs; Freddie Hart’s Loose Talk, a classic country cheating song performed as a duet with Claire Lynch; Far Side Bank of Jordan a superb, understated version of the well-loved gospel song; and Ben E. King’s Stand By Me, which is given a delicate traditional country arrangement without losing any of its soul.  

Love is the prevailing theme, from the deeply romantic O What A Thrill through the sensual Bless Your Foolish Heart to the sexual tension of Wear Me Out with its repetitive rhythm creating an hypnotic effect. Jesse’s approach to lyrics is gracefully poetic but direct—no self-indulgent clouds or impenetrable metaphors here. The rootsy, spare production and palpable humanity in the mix are also strong points. Amongst the tasteful pickers you’ll hear Jerry Douglas, Russ Barenberg, Andy Leftwich, Mark Fain, Bruce Dees and Guthrie Trapp presenting a delightfully understated vibe.

In 2007, Jesse received a Lifetime Achievement Award from ASCAP to honour his songwriting prowess. Four years later he was diagnosed with cancer of the oesophagus and had to undergo treatment for the next couple of months and was eventually given the all clear from his doctor and resumed his career. In September 2012, various artists including James Taylor, Lucinda Williams, Vince Gill and Jimmy Buffett performed covers of Winchester's tunes for a tribute album called QUIET ABOUT IT, which was released on Buffett’s Mailboat Records.

Early in 2014 the cancer returned whilst Jesse was in the midst of recording a final album, A REASONABLE AMOUNT OF TROUBLE, which is due for release on Appleseed this July.

Jesse Winchester’s songs have been a part of my life for more than 40 years. A purveyor of laid-back timeless music that acknowledges the diverse elements found in southern culture. It’s possible to detect traces of the blues, country, rockabilly, bluegrass, r&b, gospel, Cajun and even jazz in his music: a virtual synthesis of Americana.

Dubbed with the dreaded folkie tag for too long, Jesse Winchester was closer to the complete tunesmith; his songs varied, from a fairly straightforward, but still beautiful country vibe to a bluesy r&b groove. Religion features a lot in his lyrics, but that is not because he was an overly righteous person. The religious references in his lyrics came from his upbringing as a Catholic.

His yearning for rustic purity was almost religious in its intensity and the tender love songs like Every Word You Say and Wintry Feeling reflect this on every level. He used music as a vehicle to express all that was inside him. From feelings on personal pride to partisan politics, his songs are so much a part of him that it’s safe to say that he was one performer who really believed in what he was singing. Quite obviously, he exposed himself as an idealist. Yet somehow his music comes across as being directed rather than preached at you. His philosophies open your eyes rather than depress you. And there aren’t many artists who could achieve that reaction.

One thing I’m sure of, he was too darn good to be dismissed simply as a cult figure. His albums remind us what good music really sounds like. His songs are all so real and vivid that it’s somehow inconceivable that they never existed before he put them there—each one an instant standard—at least they would be thus recognised if ever they were to get heard by the mass public.

For someone who is so little known, surprisingly all of his albums are still readily available. Truly, Jesse Winchester merits all the superlatives, and you owe it to yourself to check out his albums.