Winchester was best known as a songwriter. His works were recorded by many notable artists, including Patti Page, Elvis Costello, Jimmy Buffett, Joan Baez, Anne Murray, Reba McEntire, the Everly Brothers, Lyle Lovett, and Emmylou Harris. A number of these recordings achieved positions on various charts.\n', '

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.\n', '

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.\n', '

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