His big film break came in his role in 1995's Mr. Holland's Opus. He has continued landing television and movie roles and co-starred as "Greg Sparks" in the late-1990s television series Sparks with James L. Avery, Sr. and Miguel A. Nunez Jr. Howard also appeared in Ashanti's music video for her 2002 single "Foolish" and in Mary J. Blige's video for "Be Without You".
oward has a longstanding reputation in the African-American community as a solid acting talent who often portrays provocative, even frightening characters, such as Cowboy in Dead Presidents or the memorable Quentin in The Best Man. Though he has recently gained popularity in films like Hustle & Flow (for which he also rapped), Crash, and Four Brothers, he stands out as a modest actor who insists on sharing the spotlight with his co-stars.
In 2005, he received both Golden Globe and Oscar nominations for his role in Hustle & Flow. In July of 2006, Howard was cast opposite Richard Gere and Jesse Eisenberg in Spring Break in Bosnia, a comic thriller in which he will play a cameraman in Bosnia; the film will be released in 2007.
As of October 10th, he has been cast as Jim Rhodes in the big screen adaptation of the Marvel Comics Superhero Iron Man.