Biography

When Southern-based singer-songwriter Jesse Winchester died in April 2014 after the cancer that had threatened his life in 2011 fatally recurred, he left behind a legacy as a songwriter’s songwriter – and "A Reasonable Amount of Trouble," a 12-song CD containing nine new Winchester compositions written and recorded while his cancer was in remission.

If you listen to many of the songs Jesse Winchester wrote in his four-decade musical career, you’ll hear most of the elements of what’s become known as “Americana” – detailed, empathetic stories of everyday people set to music incorporating folk, country, bluegrass, blues and gospel instrumentation.

How ironic, then, that a musician with such a strong sense of personal and musical roots would make the life changing decision to leave his Memphis home in 1967 and resettle in Canada in defiance of his draft notice, a.k.a. an invitation to fight in Vietnam.

Born on the army base – another irony – in Bossier City, La., where his father was stationed, Jesse was mostly raised in Memphis, where the Winchester name was well-established in local politics and society. There were ten years of piano lessons ahead, playing guitar in high school bands, and attendance at Williams College in Massachusetts.

But in the mid-Sixties, graduating from college almost inevitably led to military service, and Jesse soon received his draft notice back in Memphis. Aware of the consequences, he bought a one-way ticket to Montreal and fly north with his guitar and a few hundred dollars.

After a few years of playing piano in Canadian bars and teaching himself to write songs, Jesse met Robbie Robertson, lead guitarist and main writer for The Band, the legendary quintet of former Dylan backing musicians, “through a friend of a friend.” Robertson produced Jesse’s self-titled debut album, enlisting fellow Band-mate Levon Helm on drums and mandolin and whiz-kid musician Todd Rundgren as engineer. That first album was released with the most low-key packaging possible – no lyrics and few credits.

Fortunately, Jesse’s songs spoke for themselves. That first album included reputation-building original compositions like the homesick “Yankee Lady,” “Biloxi,” “Brand New Tennessee Waltz” and the rollicking “Payday.”

Although his inability to tour the US hampered his career until President Carter declared amnesty for draft defiers in 1977, Winchester 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 and The Mavericks had Top 10 country hits with “I’m Gonna Miss You, Girl” and "O What a Thrill," respectively, both of which Jesse finally recorded for his 2009 "Love Filling Station" CD. Reba McIntyre and Wynonna Judd have been among the most regular outlets for his songs. Jesse even had his own Top 40 hit with “Say What” in 1981.

After releasing seven albums between 1970 and 1981, Jesse took some time off to recharge, living on the royalties from his songs. He only recorded two additional studio albums in the next two decades. In 2002, Jesse and his new wife finally relocated back to the States, in Virginia.

Sadly, some of the inspiration behind the original songs on his final album, "A Reasonable Amount of Trouble," to be released posthumously by Appleseed in September 2014, was the emotional and physical rollercoaster of contacting esophogeal cancer in 2011, recovering successfully from surgery and related treatments, only to have the cancer recur in his bladder two years later.

Despite, or because of, his medical problems, Jesse still managed to write typically moving songs of life’s transient pleasures (“All That We Have is Now”), tongue-in-cheek rockers (“Never Forget to Boogie”), and his peace with his fate (the heartwrenching “Just So Much,” which closes the CD). "A Reasonable Amount of Trouble" is tinged with sadness but not a drop of self-pity. There’s Jesse’s trademark humor, insight, tenderness, and even new versions of the sweet oldies Jesse enjoyed so much (“Rhythm of the Rain,” “Devil or Angel,” and “Whispering Bells”).

The new CD was produced by Mac McAnally, who also plays lead guitar (and has performed both functions for Jimmy Buffett, among others, for years). Jesse plays acoustic guitar and keyboard and sings in his uniquely weightless tenor, there’s an attuned rhythm section, and guest appearances by “newgrass” country Grammy winner Jerry Douglas on lap steel and legendary saxophonist Jim Horn, among others.

Jesse received a Lifetime Achievement Award from the American Society of Composers, Authors and Publishers in 2007. This fall he will be posthumously inducted into the Memphis Music Hall of Fame.