<P> Winchester was born at Barksdale Army Air Field, near Bossier City, Louisiana, and raised in northern Mississippi . Winchester was one of three children born to James Ridout Winchester Sr. (1917 - 1962) and Frances Ellyn Manire Winchester (1920 - 2010). Through his father's side, he is part of the Lee family of Virginia (Henry Lee II and Richard Henry Lee were two of his 4th - great - grandfathers). In 1952, after a heart attack left his father unable to farm, his family moved to Memphis, Tennessee, where he graduated from Christian Brothers High School 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 military service . "I was so offended by someone's coming up to me and presuming to tell me who I should kill and what my life was worth," he told Rolling Stone magazine in 1977 . </P> <P> Winchester began playing guitar in bands while still in high school . He played in Germany during college study abroad and after graduation . Upon arriving in Quebec in 1967, he joined a local band, Les Astronautes . He also began writing songs, which he performed as a solo artist at the Montreal Folk Workshop and at coffeehouses throughout eastern Canada, adding impetus to a revival in folk music that was taking place across Canada . Under the auspices of the Band's Robbie Robertson, another Canadian, Winchester began his recording career in 1970 with a self - titled album released on the Ampex label . </P> <P> Winchester released several albums during the 1970s . Because of his status as a draft resister, he was unable to tour in the United States, and he became recognized primarily as a songwriter . His best - known songs include "Yankee Lady", "The Brand New Tennessee Waltz", "Mississippi, You're on My Mind", "A Showman's Life", and "Biloxi". These and others have been recorded by numerous artists . </P> <P> In 1974, Winchester often performed at the Hotel Le Chatelet in Morin Heights, Quebec, run by several expatriate Tennesseans who had come to Canada in 1972 . David "Butch" McDade and Jeff "Stick" Davis moved to Quebec to become part of Jesse Winchester and the Rhythm Aces . Winchester was the first to record the songs "Third Rate Romance" and "The End Is Not in Sight", both written by Russell Smith . Smith traveled to Montreal to assist in the recording of the album Learn to Love It at Studio Six . Smith, Davis and McDade later were original members of the Amazing Rhythm Aces . </P>

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