While still in his teens, Jesse moved to New York City where he soaked up much of the classic Jazz scene. In New York, he performed at Windows on the World on the 107th floor of the former World Trade Center, the Spy Bar in SoHo and Lansky's Lounge in the East Village. Returning to his native Toronto, Jesse began working with Canadian music legend Jeff Healey. In a June 2002 interview with Vintage Guitar magazine Healey said "I have a full-time guitar player name's Jesse Barksdale, who, in my opinion, is the finest jazz guitar player, all-around, in this country." Jesse has performed at festivals in the United States, Mexico and France including Festival Django Reinhardt Samois sur Seine. In Canada he has appeared at all of the major Jazz festivals.