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His other television roles include federal agent Mike Giardello in the NBC series Homicide: Life on the Street (1998–1999), Sidney Glass / Magic Mirror in the ABC fantasy series Once Upon a Time (2011–2017), Tom Neville in the NBC series Revolution (2012–2014), Dr. Edward Ruskins in the Netflix series Dear White People (2017–2021), Stan Edgar in the Amazon series The Boys (2019–present) and The Boys Presents: Diabolical (2022), and Moff Gideon in the Disney+ series The Mandalorian (2019–2023), the lattermost of which earned him two Primetime Emmy Award nominations. He also portrayed Adam Clayton Powell Jr. in the MGM+ series Godfather of Harlem (2019–present), acted in the HBO drama series Westworld (2016), and starred in the Netflix television series Kaleidoscope (2023), The Gentlemen (2024), and The Residence (2025).

He is also known for his collaboration with Spike Lee, acting in several of his films, such as School Daze (1988), Do the Right Thing (1989), Mo' Better Blues (1990), and Malcolm X (1992). His other major films include Taps (1981), King of New York (1990), Bob Roberts (1992), Fresh (1994), The Usual Suspects (1995), Ali (2001), Monkeybone (2001), Last Holiday (2006), Rabbit Hole (2010), Okja (2017), Megalopolis (2024), MaXXXine (2024), and Captain America: Brave New World (2025). He voiced Akela in the live-action remake of The Jungle Book (2016).