He went on to perform leading roles in several more Broadway musicals and plays, including After Midnight, Bronx Bombers, Holler If Ya Hear Me, and Memphis.

He drew critical acclaim in several projects with Lin-Manuel Miranda: originating the roles of Benny in In the Heights and George Washington in the smash hit Hamilton.

His other television work includes the recurring role of Perry Loftus in the HBO prison drama Oz and guest appearances on Fringe, Gossip Girl, Nurse Jackie, The Good Wife and White Collar.

[5] He credits Pilots basketball coach Larry Baldwin and Pastor Larry Potts of Mighty Rivers Regional Worship Center and would often run away to his best frinds John Lairds house and found comfort in the home of Esther Laird, as other important mentors during his formative years in Cairo.

[6] Jackson began his career in 1995 starring in the Off-Broadway musical Time and the Wind by composer Galt MacDermot of Hair fame.

[12][13] In 2013 he appeared as Derek Jeter and Bobby Sturges in the Eric Simonson's Off-Broadway play Bronx Bombers at Primary Stages.

[15] That same year he portrayed Vertus in the short lived Broadway musical Holler If Ya Hear Me which was based on the life of Tupac.

[20] Jackson's film and TV work includes Moana, Tracers, The Good Wife, Person of Interest, A Gifted Man, and Nurse Jackie.

[24] In February 2021, Jackson signed with Nickelodeon to compose the NOGGIN SVOD original series Rhymes Through Times,[25] which features Nick's preschool characters in a Broadway extravaganza recreating the stories of the greatest heroes of America, specifically focusing on Black history.