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After training at the American Conservatory Theater, Washington began his career in theatre, acting in Off-Broadway performances. He first came to prominence in the NBC medical drama series St. Elsewhere (1982–1988), and in the war film A Soldier's Story (1984). Washington won Academy Awards for Best Supporting Actor for playing an American Civil War soldier in the war drama Glory (1989) and for Best Actor for playing a corrupt police officer in the crime thriller Training Day (2001). He was Oscar-nominated for his roles in Cry Freedom (1987), Malcolm X (1992), The Hurricane (1999), Flight (2012), Fences (2016), Roman J. Israel, Esq. (2017), and The Tragedy of Macbeth (2021).

Washington has starred in other notable films, including The Pelican Brief, Philadelphia (both 1993); Crimson Tide, Devil in a Blue Dress (both 1995); He Got Game (1998); Remember the Titans (2000); Man on Fire (2004); Déjà Vu, Inside Man (both 2006); American Gangster (2007); Unstoppable, The Book of Eli (both 2010); The Equalizer trilogy (2014–2023), Gladiator II (2024), and Highest 2 Lowest (2025). Washington has also directed the films Antwone Fisher (2002), The Great Debaters (2007), Fences (2016), and A Journal for Jordan (2021).

On stage, he has acted in The Public Theater productions of Coriolanus (1979) and The Tragedy of Richard III (1990). He made his Broadway debut in the Ron Milner play Checkmates (1988). He won the Tony Award for Best Actor in a Play for his role as a disillusioned working-class father in the Broadway revival of August Wilson's play Fences (2010). He has also acted in the Broadway revivals of William Shakespeare's Julius Caesar (2005) and Othello (2025), Lorraine Hansberry's play A Raisin in the Sun (2014), and Eugene O'Neill's play The Iceman Cometh (2018).