His breakout role in 1995's Mr. H... olland's Opus helped pave the way for Howard's film career, as did his critically acclaimed performance as Cowboy in the Hughes brothers film Dead Presidents. By the time he took the role of Quentin in 1999's The Best Man, Howard had established a reputation as an actor of both skill and integrity, respected by the film industry as well as the black community. The new millennium finally brought Howard the kind of work that not only showcased his talent but made him a well-known name.

His role in the controversial Paul Haggis film Crash, as well as his work in the John Singleton's Four Brothers brought him to the attention of both mainstream audiences and critics. He also attracted the spotlight on the small screen around this time with parts in the acclaimed TV films Their Eyes Were Watching God with Halle Berry, and Lackawanna Blues with S. Epatha Merkerson. This set the stage for his career-making performance as a pimp desperate to create a new life for himself as a musician in Hustle & Flow, for which he earned an Oscar nomination.

Never one to rest for long, Howard soon moved on to take a role in 50 Cent's semi-autobiographical Get Rich or Die Tryin', as well as the musical Idlewild.