[1] He played drums as a young child, making appearances with Count Basie, Duke Ellington, Woody Herman, and Buddy Rich before he finished high school.

In 1971 he relocated to Los Angeles, where he played with Monty Alexander, Ray Brown, Herb Ellis, Lena Horne, Milt Jackson, and Barney Kessel.

In the 1980s, Jackson worked with Lionel Hampton, Al Jarreau, James Moody, and Sonny Stitt, and in 1985 re-joined the Basie orchestra while Thad Jones was its leader.

Following this he worked with Illinois Jacquet and Artie Shaw, then re-joined the Basie Orchestra under Frank Foster.

In the 1990s, he relocated to Fort Lauderdale, where he played with Harry Allen, Billy Ross, and the Manhattan Transfer; Jackson moved to Nashville, TN in the late 2000s and started to front his own big band.