He has also had major roles in feature films such as Me, Myself & Irene (2000), Kangaroo Jack (2003), Agent Cody Banks 2: Destination London (2004), Hustle & Flow (2005), The Departed (2006), Transformers (2007), and Scream 4 (2011).

He has appeared as a regular judge on Food Network's Iron Chef America and had roles on other television programs such as All About the Andersons, The Bernie Mac Show, Guys with Kids, and The Shield.

His stepfather, Sterling Bowman, was a native of Little Rock, Arkansas, who moved to Los Angeles to work in the steel mill industry before opening a chain of three clothing stores.

[6] Although this experience was a blow to his ego, he met his future friend and fellow comedic actor Guy Torry there, who consoled him after the show and encouraged him to keep getting up on stage.

He initially enrolled at Howard University as a theater major but faced financial difficulties, leading him to leave after his junior year.

[10] Anderson's early television work includes a lead role as Teddy Broadis in the teen series Hang Time, and many one-off guest appearances on shows such as NYPD Blue, Malcolm & Eddie, In the House, and Ally McBeal, as well as recurring roles on series like 'Til Death and The Bernie Mac Show.

[13] Anderson joined the cast of the long-running NBC crime drama television series, Law & Order in 2008.

[17] Before his work in Law & Order, Anderson starred in two other crime series, Fox's K-Ville (as one of the lead characters) and FX's The Shield.

[19][20] In 2013, Anderson signed on to host the celebrity-driven, family game show called Wall of Fame,[21] which was produced by Endemol USA for NBC.

In the Ultimate Bar Food battle, he served as bartender/sous-chef for Iron Chef Bobby Flay opposite Masaharu Morimoto and fellow judge Simon Majumdar.

[23] In 2014, Anderson began starring as Andre "Dre" Johnson on the ABC sitcom Black-ish,[24] which completed its eight-season run in 2022.

"[36] The telecast was met with mixed reviews and some criticism, in particular, regarding a recurring bit in which Anderson's mother interrupted acceptance speeches that went on too long.

Some on social media cited the moment when Anderson's mother interrupted a speech given by Jennifer Coolidge, who won for The White Lotus, as being "rude" and "disrespectful".

Further settlement agreements stated that Anderson was to relinquish his Glock 19 firearm to law enforcement within 30 days of the divorce finalization.

The alleged victim accused Anderson and assistant director Wayne Witherspoon of forcibly removing her clothing, photographing her naked body, and sexually assaulting her.

A witness claimed to have heard the alleged victim's screams and to have seen her run naked from the trailer, and she was treated at St. Francis Hospital.

[50] Due to lack of evidence on September 4, the Los Angeles District Attorney's Office decided not to press charges against Anderson.