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Henderson is known mostly for his stage work. 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. He portrayed Jim Bono in the Broadway revival of August Wilson's Fences, starring Denzel Washington, for which Henderson received a Tony Award nomination as a supporting actor, as well as the Richard Seff Award from Actor's Equity; he reprised the role in Washington's 2016 film adaptation. Also in 2016, Henderson appeared in Kenneth Lonergan's Manchester by the Sea, starring Casey Affleck and Michelle Williams, playing the boss of Affleck's character. Previously, he appeared as Van Helsing in the Broadway production of Dracula, the Musical. More recently, he played the role of Father Leviatch in Greta Gerwig's 2017 film Lady Bird. On Broadway, he has performed in Drowning Crow, the revival of Ma Rainey's Black Bottom, and the