Henson made his acting debut starring as Lem Van Adams in the Showtime drama series, Soul Food (2000–2004), for which he received two NAACP Image Awards nominations.

He later appeared in films The Salon (2005), Stomp the Yard (2007), The Express: The Ernie Davis Story (2008), Tekken (2009), Black Coffee (2014), and Chocolate City (2015).

[3] Henson is also known for his instructional dance video Darrin's Dance Grooves (which was heavily marketed in 2001 and 2002),[1] As an actor, Henson made his Broadway debut appearing in Ron Link's playStand-up Tragedy in 1990,[4] and later performed in off-Broadway of David E. Talbert's play Fabric of a Man.

He made his television debut appearing as a dancer in the 1999 made-for-television drama film Double Platinum starring Diana Ross and Brandy.

[6] In 2008, Henson played football player Jim Brown in the sports film, The Express: The Ernie Davis Story.

[11] In 2018, Henson began starring in the BET crime drama series, The Family Business playing the role of Orlando Duncan.