[1] He led his own ensemble, the Krazy Kats, for recordings in 1930, and following this group's dissolution he played extensively as a solo pianist in nightclubs in New York.

[2] During this time he also accompanied singers such as Viola McCoy, Lena Wilson, Sara Martin, Martha Copeland, Helen Gross, and Clara Smith.

As house pianist at Cafe Society from 1943 until 1951 he was a success;[1] he also toured with Eddie Condon in 1946.

[citation needed] His many left hand techniques are found explained in detail in Riccardo Scivales's method, Jazz Piano: The Left Hand (Bedford Hills, New York: Ekay Music, 2005), ISBN 978-1929009657.

Jackson was married to the singer Maxine Sullivan from 1950, until his death from heart failure in 1970.