Throughout the span of Michael’s 25-year career in film and television, the star has captivated audiences and his peers. As a result, he’s earned a whopping 30 nominations spanning the Emmys, NAACP Image Awards, Screen Actors Guild Awards, and more.

In Michael’s role of Bobby McCray in Ava DuVernay’s 2019 film When They See Us, the actor played the father of Antron McCray, a Harlem native who was one of the “Exonerated Five.” In the film, Bobby urged his son to plead guilty despite not having anything to do with the crime of raping a woman in Central Park. He went on to have a non-existent relationship with Antron.

For Michael’s performance as Bobby McCray, he secured a slew of awards and nominations.

• Nominee: 2019 Emmy Award for Outstanding Supporting Actor in a Limited Series or Movie
• Nominee: 2019 Gold Derby TV Award for Movie/Limited Series Supporting Actor
• Nominee: 2019 International Online Cinema Awards (INOCA) Best Supporting Actor in a Limited Series or TV Movie
• Nominee: 2019 OFTA Best Supporting Actor in a Motion Picture or Limited Series

• Winner: 2019 OFTA Best Ensemble in a Motion Picture or Limited Series
• Winner: 2019 Black Reel Awards for Television Outstanding Supporting Actor, TV Movie/Limited Series
• Winner: 2019 AAFCA TV Honors Best Ensemble

Another one of Michael’s memorable roles was from the HBO drama series The Wire. Known for his flawless portrayal of Baltimore robber Omar Little, Michael played a character who made a living by robbing the city’s most dangerous drug dealers. Although he unfortunately meets his demise, Omar is revered as a legend in Baltimore.

Despite Michael’s portrayal of Omar Little being one of his most notable roles, he only scored two nominations for his performance.

• Nominee: 2007 NAACP Image Award for Outstanding Actor in a Drama Series
• Nominee: 2009 NAACP Image Award for Outstanding Supporting Actor in a Drama Series

Michael’s performance in HBO's 2020 horror-drama series Lovecraft Country also showcased how much of a force he was in the industry. Playing the role of Montrose Freeman, the father of Atticus, he harbors various secrets that have taken a toll on his life and his relationship with his son.

Michael was and is nominated for multiple awards and has secured some wins for his work in the series.

• Winner 2021: International Online Cinema Award for Best Supporting Actor in a Drama Series
• Winner 2021: Black Reel Awards For Television Outstanding Supporting Actor, Drama Series
• Winner 2021: Broadcast Film Critics Association Awards Best Supporting Actor in a Drama Series
• Winner 2021: Gold Derby TV Award for Drama Supporting Actor