Jackson grew up in Washington, D.C. and attended Howard University. Jackson began his broadcasting career as the first African-American radio sports announcer, broadcasting Howard’s home baseball games and local Negro league baseball games.
In 1939, he became the first African American host at WINX/Washington with The Bronze Review, a nightly interview program. He later hosted The House That Jack Built, a program of jazz and blues on WOOK.
Jackson moved to New York in 1954 and became the first radio personality to broadcast three daily shows on three different New York stations. Four million listeners tuned in nightly to hear Jackson’s mix of music and conversations with jazz and show business celebrities.
In 1971, Jackson and Percy Sutton, a former Manhattan borough president, co-founded the Inner City Broadcasting Corporation (ICBC), which acquired WLIB-AM -- becoming the first African-American owned and operated station in New York. The following year, ICBC acquired WLIB-FM, changing its call letters to WBLS ("the total BLack experience in Sound"). Today, ICBC -- of which Jackson is group chairman -- owns and operates stations in New York, San Francisco, Philadelphia, Pittsburgh, Fort Lauderdale, Columbia, S.C. and Jackson, Miss.
Now in his 90s, Jackson continues to host "Sunday Classics" on WBLS each and every Sunday, although instead of the usual 8am-4pm hours, he is now on air from 12 noon till 4pm each Sunday with Debi Jackson and Clay Berry.