He spent several years in the late 1950s touring and recording with the Five Blind Boys of Mississippi, before starting his long working relationship with Bobby Bland.
Another standout solo on Bland's "Wishing Well" displays a compelling virtuosity in the blues idiom that would become a model for young guitarists in England such as Eric Clapton who would become part of the British Invasion of the 1960s.
[citation needed] Bennett himself never liked to claim to be a blues player, preferring instead to be as versatile as he could be, and taking pride in being able to quote from a wide variety of popular music, including TV theme songs.
In 1965 he joined the Red Saunders band at the Regal Theater in Chicago, and cut his own record in 1968, an instrumental called "Casanova, Your Playing Days are Over" on the now defunct Brunswick label.
[2] He was part of Operation Breadbasket in the late 1960s, and worked with jazz musicians, including Cannonball Adderley, Sonny Stitt and Dexter Gordon,[3] as well as later with the Chi-Lites, the Lost Generation, The Hues Corporation;[4] among many others.