Jesse Winchester was a prolific and well-respected singer/songwriter in the early 1970s, but he is best known for being the most famous Vietnam draft dodger to emerge in the contemporary music scene. An aspiring singer/songwriter from the American South, Winchester chose to immigrate to Montreal when he received his draft notice in 1967 rather than stay and have to fight in a war he did not believe was justified. Winchester re-located to Canada and started making a meager living as a performer in coffee houses.
In 1969, he was introduced to Robbie Roberston, already one of Canada's biggest music stars and key member of The Band. Robertson decided to help Winchester, and was able to get him a deal with the Warners-distributed Bearsville Records, which was owned by Albert Grossman (renowned manager of The Band, Bob Dylan, and Janis Joplin).
Winchester released his first LP, simply entitled Jesse Winchester, both in the US and Canada in 1970. It received critical raves. Other albums followed and received similar response from the rock press, among them: Third Down, 110 to Go (1972), Learn to Love It (1974), and Let the Rough Side Drag (1976). But none of these titles sold in any significant quantities, due to Winchester's outlaw status. In 1973, he became a legal citizen of Canada, and it was not until President Jimmy Carter was elected in 1976 and granted amnesty to the Vietnam draft dodgers that Winchester was able to return home to the U.S.
Winchester has continued to write, record and tour, and has stayed active writing material for other artists such as Jimmy Buffet, Emmylou Harris, and Nicolette Larson.