The world lost a gift to music with the passing of Jesse Winchester on April 11 in Charlottesville. According to his website, the legendary singer songwriter ” died peacefully in his sleep, at home, after fighting bladder cancer.”
The soft-spoken country star may have been averse to thrusting himself into the public eye, but his story speaks voumes. A determined peace advocate, Winchester found himself pitted against government officials during Vietnam, ultimately leading the young musician to seek refuge in Canada.
According to The Huffington Post, it was here where he found his true beginnings in music. With only 300 dollars in his pocket, Winchester carved a new life for himself, writing music that extended across borders and politics to find a home within the sanctum of American hearts. His work includes over 100 songs written for prolific talents such as James Taylor, The Everly Brothers, Emmylou Harris, and even Raffi. Among his most renowned works are “Brand New Tennessee Waltz,” made famous by Joan Baez, and “Biloxi,” whose cover by Jimmy Buffet stands as one of the landmarks of his career.
It was love and family that eventually brought Winchester to Charlottesville. “I came back to the states because I fell in love with Cindy,” he told WNRN in 2006. “Cindy’s daughter shopped around for another place to live, with good schools, good climate, nice people, and eventually settled on Charlottesville. […] and we followed them here.” While in Charlottesville, Winchester performed at the former Gravity Lounge alongside other well-known artists like Guy Clark. For those who knew him, he was a model citizen and an embodiment of the humanist message that resonates from his lyrics.
“I knew him to be the quintessential Southern gentleman,” said Anne Williams of WNRN.
It wasn’t until late in his career that Winchester’s contributions to music were officially recognized. In 1990, he received two Juno Award Nominations, one for Best Roots & Traditional Album, and a second for Country Male Vocalist of the year. A decade later, he got another Juno nomination for his album Gentleman of Leisure.
According to NPR, Winchester was also honored with a Lifetime Achievement Award in 2007 for his contributions to country songwriting. If any doubts of Winchester’s talent still lingered, they were squashed in 2009 when, with a voice like honey, he performed his single “Sham-A-Ling-Dong-Ding,” on Elvis Costello’s “Spectacle” leaving fellow artist Neko Case in tears and rendering the loquacious Costello utterly silent.
Winchester’s legacy has been preserved in a tribute album titled Quiet About It. The record includes his most influential songs all performed by fellow artists whose careers honor his genius. His memory will continue to live through friends, family, and the lives that have been touched by his music. —Logan Boggs