In 2014, Williams received a Primetime Emmy Award nomination for his performance as Jack Gee in the HBO TV film ‘Bessie’ directed by Dee Rees.
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He was next seen in television series and shows such as ‘Detroit 1-8-7’ (2011), ‘Aqua Teen Hunger Force’ (2011), ‘Community’ (2011-2012), ‘Walk This Way’ (2013), ‘High School USA!’ (2013), ‘Lucas Bros. Boardwalk Empire ran for 5 seasons and aired its final episode in 2014.
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He portrayed Albert "Chalky" White in the series which earned a ‘Screen Actors Guild Award’ (shared with the cast).
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In 2010, he became a part of the American period crime drama television series, ‘Boardwalk Empire’ created by Terence Winter. He played the role of ‘Omar Little’ and remained a part of the series until it went off-air in 2008. In 2002, he joined the cast of the American crime drama television series ‘The Wire’ created by David Simon. He next appeared in television series like ‘Law & Order’ (2001), ‘Deadline’ (2001), ‘The Sopranos’ (2001), and ‘Third Watch’ (2002).
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While the film received mostly positive reviews from critics, it failed to achieve success at the box office. Williams made his debut in the 1996 American crime drama film ‘Bullet’ where he played the role of ‘High Top.’ In 1999, he starred in the American psychological drama film ‘Bringing Out the Dead’ directed by Julien Temple.