In the late 1870s, he joined the company of Augustus Harris and gained prominence as the leading comedian and stage manager at the Drury Lane Theatre.

[3][9] Jackson specialized in portraying caricatures of Jews in productions like Queen's Evidence, The World, and Pluck.

[2] On 12 August 1885, he revived his best known role[8] at the Pavilion Theatre, Whitechapel, that of the "disreputable Jew diamond dealer"[10] Moss Jewell in The World.

[2] That night, Jackson reportedly expressed fears about not being permitted to be buried among the Jewish community, given "his identification on the stage with the hideous caricature of a Jew [which] gave great and not unnatural offence to his coreligionists.

"[11] He died of a morphine overdose the following evening at his residence at 45 Great Russell Street, Bloomsbury, at the age of 49.