Jesse Winchester is the stage name of musician James Ridout Winchester (born May 17, 1944, in Bossier City, Louisiana)
Winchester was raised in northern Mississippi and the city of Memphis, Tennessee. He attended Williams College in Williamstown, Massachusetts, graduating in 1966. Upon receiving his draft notice the following year, Winchester moved to Montreal, Quebec to avoid military service. He became a Canadian citizen in 1973.
Winchester had begun playing guitar in bands while still a high school student. He also played in Germany during college study abroad and after graduation. Upon arriving in Quebec in 1967, he joined a local band, the Astronautes. At this time, he also began writing songs that he performed as a solo artist in coffee houses throughout eastern Canada. Under the auspices of The Band's Robbie Robertson, Winchester began his recording career in 1970 with his self-titled album, released on the Ampex label.