Anderson was born in Los Angeles, California, but grew up in Compton, California, to Doris, a telephone operator and actor; his step-father, Sterling Bowman, owns a chain of clothing stores. Anderson is an alumnus of the Los Angeles County High School for the Arts and Howard University.

Anderson first achieved recognition in the NBC television show Hang Time (1995–2000). He had a breakout role in 1999's Romeo Must Die. Since then, Anderson has starred in a number of films, including Exit Wounds, Barbershop, and Kangaroo Jack. In 2003, he got his own sitcom on The WB, All About the Andersons, co-starring John Amos. The series was cancelled after only one season. In March 2005, Anderson began co-starring in The Shield's fourth season as Antwon Mitchell, an ex-convict who poses as a community leader while still running his old street gang. His performance on The Shield earned him much acclaim from critics who had previously dismissed him as a light comedy actor, resulting in him returning to The Shield during the show's fifth and sixth seasons for a few episodes. Anderson also starred in the animated family film Hoodwinked, and had a supporting role in the Best Picture Academy Award-winning film The Departed.

Anderson starred in the live-action Transformers film, based on the 1980s cartoon Transformers. The spring of 2007 saw Anderson in another regular television role, this time as a cast member of the FOX police drama K-Ville. In 2007, Anderson was also a stand-out emcee on a number of episodes of It's Showtime at the Apollo.