A dynamic performer with incredible screen presence, African-American funnyman Anthony Anderson became an almost ubiquitous feature player beginning in 1999, providing comic relief in an impressive number of films early on in his career. The California native landed his first professional job at age five, appearing in a television commercial. Twenty years later, he could be seen on the NBC sitcom "In the House", starring LL Cool J. While Anderson's career lulled, the performer was busy with his education, attending a performing arts high school and earning a talent scholarship to the prestigious Howard University. A 1996 cameo in "Alien Avengers,” a segment of the Showtime series "Roger Corman Presents,” led to a regular role as a hefty but capable basketball player on the NBC teen series "Hang Time" (from 1997 to 1998). A guest role on "NYPD Blue" followed in 1998, predating his feature film onslaught, which began with 1999's "Life,” a 1930s prison comedy starring Eddie Murphy and Martin Lawrence.
Baby-faced enough that he was able to play teens well into his twenties but easily aged with a bit of facial hair, Anderson proved a versatile player, and followed up his role in "Life" with a part in Barry Levinson's 1950s Baltimore-set drama "Liberty Heights" and a guest turn on the UPN sitcom "Malcolm and Eddie.” The actor ushered in 2000 with credits in two episodes of "Ally McBeal" (Fox) before taking on Andrzej Bartkowiak's "Romeo Must Die,” where he played a bumbling bodyguard. He reunited with Martin Lawrence as an over-ambitious security guard in "Big Momma's House" and played one of a group of film students targeted by a mysterious murderer in "Urban Legends: Final Cut.” He was given more room to strut his stuff in "Me, Myself & Irene" as Jamaal, the most vocal of Jim Carrey's overgrown triplet sons (born to his wife after an affair with an African-American midget). One of the few well-rounded roles in the Farrelly brothers film, Jamaal was foul-mouthed but well-educated, and unexpectedly respectful of his father, the town pushover.
Anderson played David Arquette's postal colleague and confidant in the inane comedy "See Spot Run" in 2001. That year saw him with breakout roles in the actioner "Exit Wounds" and the funeral-set feature "Kingdom Come.” Reuniting with Bartkowiak and DMX on the former, Anderson brought much-needed comic relief to the casualty-heavy Steven Seagal caper, working with Tom Arnold to make a genuinely funny if unexpected comedy pair. In "Kingdom Come,” Anderson won raves as the worthless womanizing husband of demanding Jada Pinkett Smith. Later that year, the actor was featured in the romantic comedy "Two Can Play That Game."
He starred, alongside Jerry O'Connell, as a New Yorker on the lam in the Australian Outback comedy "Kangaroo Jack" and then reunited with DMX for the action feature "Cradle 2 the Grave" before returning to comedy with supporting turns in Jamie Kennedy's "Malibu's Most Wanted" and the horror-spoof sequel "Scary Movie 3" (all in 2003). That same year he co-created and starred in the short-lived sit-com "All About the Andersons" (2003) as a struggling actor who moves in with his parents to provide a stable environment for his young son.
Anderson's feature career continued unabated: along with Eddie Griffin and Michael Imperioli, he headlined the limp relationship comedy "My Baby's Daddy" (2004) as part of a trio of immature men suddenly saddled with responsibility when their girlfriends all become pregnant. Then it was on to a co-starring role in the family-friendly sequel "Agent Cody Banks 2: Destination London" (2004) as Derek, the handler for Frankie Muniz's underage secret agent. Anderson then took on a recurring role during the 2005 season of the gritty crime drama "The Shield," playing the influential and menacing ex-con Antwon Mitchell, delivering his most compelling and complex performance to date.
Anderson next appeared in “King’s Ransom” (2005) as a millionaire businessman who devises a plot to kidnap himself in order to avoid a messy and expensive divorce from his wife (Kellita Smith). The plan goes awry, however, when he discovers that he’s not the only one who wants to kidnap him. Far better was his measured turn in the acclaimed indie drama "Hustle & Flow" (2005) as Key, the aspiring but frustrated rap producer who hopes a surprisingly talented pimp (Terrence Howard) will at last provide his ticket to success. After appearing on a couple episodes of the cable comedy “Campus Ladies” (Oxygen Media, 2005- ), Anderson showed up as a gay cowboy in a parody of Ang Lee’s “Brokeback Mountain” (2005), one of many Hollywood movies getting the David Zucker treatment in “Scary Movie 4” (2006).
For his next project, Anderson joined an all-star cast that included Matt Damon, Leonardo DiCaprio, Mark Wahlberg and Jack Nicholson in “The Departed” (2006), Martin Scorsese’s slick crime thriller that was loosely based on the excellent Hong Kong actioner “Infernal Affairs” (2002). “The Departed” centered on a South Boston cop (DiCaprio) deep undercover inside a crime syndicate ran by Franck Costello (Nicholson), a sexually deviant mob boss who has one of his own gangsters (Matt Damon) inside the police department. As the police struggle to bring down the Costello’s operations, the mob boss manages to stay one step ahead while trying to flush out the mole that he learns has infiltrated his crew. Meanwhile, both moles fight to expose the other before their own cover is blown. “The Departed” received a huge helping of critical kudos prior to its early October release.