Jackson began his career in the 1980s as a session musician playing bass guitar for an array of jazz, pop, rock, and R&B performers. He moved on to work in music production and in the A&R department at Columbia Records and MCA Records. Jackson is best known from his appearances as the longest-serving judge on American Idol and executive producer for MTV's America's Best Dance Crew.

In May 2020, Jackson was rehired as bassist for Journey following their sudden split with founding member Ross Valory. Jackson had previously filled the role on the band's 1986 album Raised on Radio and its tour.

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