Jackie Washington grew up in Hamilton, Ontario's sizable Black community and started performing music at the age of five. He was a member of the Washington Brothers, whose sound was heavily influenced by the Mills Brothers, until the end of the 1930s. Washington left music as a profession during the '40s, but started singing in night clubs during the '50s. His debut album as a blues artist, Blues and Sentimental, was released in 1976. He played at folk and blues festivals throughout Canada, never venturing south of the border into the United States (where his grandparents had been slaves), and had a total of 1,200 songs at his fingertips. Washington's work transcended the folk and blues scenes, bringing him into contact with Duke Ellington, Clark Terry, and Lionel Hampton, among other jazz giants, as well as bluesmen Sonny Terry, Brownie McGhee, and Lonnie Johnson.