Jackson began his career in 1995 starring in the
Off-Broadway musical
Time and the Wind by composer
Galt MacDermot of
Hair fame. He made his Broadway debut in 1997 as an ensemble member and the understudy for Simba in the Original Broadway Cast of
The Lion King. He then did work in the theater scenes in Chicago and Minneapolis–Saint Paul, notably earning a BATC Award nomination for Best Actor for ''
Beggar's Holiday'' in 2004 for and winning a
Joseph Jefferson Award (Chicago's equivalent to the Tony Awards) in 2006 for
Comfortable Shoes. In 2007 he returned to New York to join the cast of the
Off-Broadway musical
In the Heights as Benny. The cast won the 2007
Drama Desk Award for Outstanding Ensemble Performance. He continued with the show when it moved to Broadway in 2008. In 2009 Jackson was tapped to write music for the revived children's television program
The Electric Company. In 2012 he returned to Broadway as Delray in
Memphis, and in 2013 he replaced
Everett Bradley as "Diga Diga Doo" in the Broadway musical
After Midnight. In 2013 he appeared as Derek Jeter and Bobby Sturges in the
Eric Simonson's
Off-Broadway play
Bronx Bombers at
Primary Stages. He remained with the production when it moved to Broadway in 2014. 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. In 2015, Jackson originated the role of President
George Washington in the musical
Hamilton on Broadway. He was nominated for a Tony Award and concluded his run on November 13, 2016 being replaced by
Nicholas Christopher. Beginning with the 2016–2017 season, he played Chunk Palmer in the CBS courtroom drama
Bull until the series' conclusion.6 Jackson's film and TV work includes
Moana,
Tracers,
The Good Wife,
Person of Interest,
A Gifted Man, and
Nurse Jackie. He is also a member of
hip-hop group
Freestyle Love Supreme. He has been nominated for three Emmy Awards for composing music and lyrics for television; he won the “Outstanding Original Song” Emmy Award in 2011 for his lyrics to "What I Am," which he co-wrote for
Sesame Street with Bill Sherman. The success led to a first look deal at
CBS Studios. In February 2021, Jackson signed with Nickelodeon to compose the NOGGIN SVOD original series
Rhymes Through Times, which features Nick's preschool characters in a Broadway extravaganza recreating the stories of the greatest heroes of America, specifically focusing on
Black history. The animation for the show was done by LionForge Animation LLC. who have previously worked on the Oscar-winning Netflix movie
Hair Love. The second season dropped on March 7, 2022. On 3 June 2025, he’s set to make his Broadway return as Davis in
''Hell's Kitchen''. ==Personal life==