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Henderson trained at Juilliard School for acting and later became a resident member of the Repertory Theatre of St. Louis from 1976 to 1981. He came to prominence as a character actor often performing the plays of August Wilson. He has received nominations for two Tony Awards, a Drama Desk Award, and two Screen Actors Guild Awards. Henderson made his Broadway debut in Wilson's King Hedley II in 2001. 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 also acted in the Broadway revival of A Raisin in the Sun in 2014. Additional Broadway credits:
Ma Rainey's Black Bottom, Drowning Crow, Dracula, the Musical, A Doll's House, Part 2. Off-Broadway: A Raisin in the Sun, Zooman and the Sign, Jitney, The Last Days of Judas Iscariot, Seven Guitars.

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