He later earned Tony Award nominations for his performances in Wilson's Fences in 2010 and Stephen Adly Guirgis's Between Riverside and Crazy in 2023.

He made his film debut in A Pleasure Doing Business (1979) and has since appeared in Extremely Loud & Incredibly Close (2011), Lincoln (2012), Fences (2016), Manchester by the Sea (2016), Lady Bird (2017), Dune (2021), Causeway (2022), Beau Is Afraid (2023), and Civil War (2024).

[2] He spent a year at Lincoln University, Missouri and was originally part of Group 1 at the Juilliard School Drama Division before he left.

He won the 2015 Obie Award for Best Actor for his starring role of Walter "Pops" Washington in the Atlantic Theatre Company and Second Stage productions of the Pulitzer Prize-winning play Between Riverside and Crazy.

On Broadway, he performed in Drowning Crow, the revival of Ma Rainey's Black Bottom, and the premiere of King Hedley II.

[5] His signature August Wilson role is the gossipy Turnbo in Jitney, for which he won a Drama Desk Award as part of the ensemble.

[citation needed] In 2005 Henderson appeared as Pontius Pilate in the production of The Last Days of Judas Iscariot directed by Philip Seymour Hoffman at the Public Theater.