Early life Winchester was one of three children born to James Ridout Winchester Sr. (1917–1962) and Frances Ellyn Manire Winchester (1920–2010). He was born at
Barksdale Army Air Field, near
Bossier City, Louisiana, and raised in northern
Mississippi through age 12, when his family relocated to
Memphis, Tennessee. He graduated from Christian Brothers High School in Memphis in 1962 as a merit finalist, a National Honor Society member and the salutatorian of his class. He graduated from
Williams College, in
Williamstown, Massachusetts, in 1966. Upon receiving his
draft notice the following year, Winchester moved to
Montreal, Quebec, Canada, to
avoid the draft. Winchester began his career in Germany. Upon arriving in Quebec in 1967, he joined a local band, Les Astronautes. He began writing songs, which he performed as a solo artist at the Montreal Folk Workshop and at coffeehouses throughout eastern Canada. Discovered by the
Band's
Robbie Robertson, Winchester released his album
Jesse Winchester, produced by Robertson. He toured Canada, opening for the Band.
Career Winchester released albums in the 1970s, but was unable to support the albums by touring in the U.S. because of his status of being a draft dodger. On June 10, Winchester appeared with
Little Feat,
Emmylou Harris and
Bonnie Raitt on Burt Sugarman's
The Midnight Special. In 1981, he had his first Top 40 U.S. hit single, "Say What", which earned No. 32 on the
Billboard Hot 100. The single was from his Bearsville Records album release, "Talk Memphis". "I'm Gonna Miss You, Girl", written by Winchester, was recorded by
Michael Martin Murphey and released in October 1987 as the lead single from the album
River of Time. The song peaked at No. 3 on the Billboard Hot Country Singles
Hot Country SNo. chart and at No. 4 on the Canadian RPM C
e Filling Station.
Later career Winchester was nominated for the
Best Country Male Vocalist award at the
Juno Awards of 1990. In 2002, he moved back to
Memphis with his girlfriend, Cindy. That year, his song "Step by Step", from the album
Let the Rough Side Drag, was used as background music for the montage that ended the first season of the television program
The Wire. He received a Lifetime Achievement Award from the
American Society of Composers, Authors and Publishers in 2007. Winchester continued to record and perform throughout the U.S. and Canada, releasing his 10th studio album,
Love Filling Station, in 2009. On April 11, 2014, Winchester died from bladder cancer in his sleep at his home. He was 69 years old. He was survived by his wife, Cindy, and three children from a previous marriage: James, Alice and Marcus Lee.
Quiet About It, a tribute record to Winchester, was released in 2012, featuring 11 artists, including
James Taylor,
Lyle Lovett,
Lucinda Williams,
Rosanne Cash and
Jimmy Buffett. Winchester's final CD,
A Reasonable Amount of Trouble, was released in September 2014, with liner notes by
Jimmy Buffett. It was nominated for two Grammy awards. ==Discography==