Jesse Winchester was born in Bossier City, Louisiana. As a child, he was raised on country farms owned by his parents and later lived in Memphis, Tennessee. Upon receiving his draft notice in 1967, to dodge the Vietnam War, he moved to Montreal with only a suitcase and a couple of hundred dollars in his pockets. After briefly gigging with Les Astronautes, a pop-rock band from Shawinigan, he decided to go solo and perform in coffee houses throughout Eastern Canada.

When I connected with him in 1971, he was struggling financially which most likely inspired the words to his song Payday… “I've been living from hand to mouth for what must be three or four weeks, and I can tell you one thing Jack, you listen when your stomach speaks.” In 2007, Jesse Winchester received a Lifetime Achievement Award from ASCAP - The American Society of Composers, Authors and Publishers.