Since the early 2000s, Anthony Anderson has made a name for himself in comedic television shows and movies, while also surprising audiences every so often with some more dramatic fare. Beginning in bit parts and charismatic supporting roles, Anderson quickly gained the attention of important Hollywood players.

After multiple shows he starred in ended after a single season, Anderson successfully produced and headlined Black-ish, which has been nominated for 25 Emmys going into its eighth and final run. Despite things not always working out, Anderson has starred in some great movies and shows over the years.

10 Harold & Kumar Go To White Castle (2004) – 7.0

Rent On Apple TV

In a short but memorable role, Anderson plays a Burger Shack Employee in Harold & Kumar Go To White Castle. When the duo is questioning at a Burger Shack drive-through window whether or not to drive to the titular restaurant instead, it’s Anderson’s character that helps convince them to make the journey.

With a supporting cast including Neil Patrick Harris, Ryan Reynolds, and Fred Willard, the movie received surprisingly positive reviews for a stoner comedy and went on to spawn the sequels Harold & Kumar Escape from Guantanamo Bay and A Very Harold & Kumar 3D Christmas.

9 Liberty Heights (1999) – 7.0

Stream On Kanopy

From Rain Man director Barry Levinson, Liberty Heights illustrates Baltimore residents as they grapple with the animosities between the Black and Jewish communities. In his first movie role, Anderson appears in the dramedy as Scribbles, a friend of local drug dealer Little Melvin (Orlando Jones).

The movie made little returns at the box office but was favorably reviewed by critics. The cast also includes Adrien Brody, Ben Foster, and David Krumholtz.

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8 Transformers (2007) – 7.0

Stream On HBO Max & Max Go

In the first Transformers movie, Anderson plays Glen Whitmann, a nerdy hacker and friend of former NSA analyst Maggie Madsen (Rachael Taylor). Serving as comic relief, Anderson’s character provides moments of humor in the mostly action-focused movie.

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Transformers was a box office hit and has since added six additional movies to the franchise. The cast includes Shia LaBeouf, Tyrese Gibson, Jon Voight, and Megan Fox in one of her best films.

7 The Bernie Mac Show (2001-2006) – 7.1

Stream On Hulu, Amazon Prime, Peacock & Tubi

The Bernie Mac Show follows the titular character and his wife Wanda (Kellita Smith) as they help raise his sister’s kids while she’s in rehab. Anderson appears in season 5 as the father of one of Bernie’s nieces, Bryana (Dee Dee Davis).

The show aired on Fox for five seasons before being canceled and was nominated for four Emmys during its run. Over the course of the seasons, multiple celebrities made cameos that stole the show, including Halle Berry, Chris Rock, and Ice Cube.

6 Black-ish (2014-2022) – 7.1

Stream On Hulu

In the popular ABC sitcom, Anderson plays Dre Johnson, an ad man grappling with his cultural identity while trying to raise his kids in a mostly white upper-middle-class neighborhood. Tracee Ellis Ross plays his wife Rainbow, considered one of the best characters on Black-ish, a bi-racial anesthesiologist.

Black-ish has had a number of recognizable recurring cast members throughout its seasons, including Wanda Sykes, Raven-Symoné, and Rashida Jones, and its success has led to the spin-offs Grown-ish and Mixed-ish.

5 Hustle & Flow (2005) – 7.3

Stream On Showtime

Hustle & Flow finds Anderson playing Key, a sound technician and friend of pimp/drug dealer DJay (Terrence Howard). When DJay finds he has a knack for rapping, Key and his sound mixer friend Shelby (DJ Qualls) help try to make DJay’s newfound dream of musical fame a reality.

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Both a critical and financial hit, the movie was nominated for two Oscars, with Three Six Mafia and Cedric Coleman winning Best Original Song in a surprise upset. Hustle & Flow also stars Ludacris, Taraji P. Henson, and Taryn Manning.

4 Law & Order (1990-) – 7.7

Stream On Peacock

In the 18th season of Law & Order, Anderson filled Jesse L. Martin’s spot after his character Ed Green was written off the show at Martin’s request, according to Entertainment Weekly. As junior detective Kevin Bernard, Anderson regularly appeared in the show until the end of its initial run.

The show has led to six spinoffs and plans to return for a 21st season in 2022, in which Anderson is set to return, according to Deadline. The show’s main cast has included Sam Waterson, Benjamin Bratt, and Jerry Orbach over the years.

3 Treme (2010-2013) – 8.2

Stream On HBO Max

From the creator of The Wire David Simon, Treme looks at the lives of residents in New Orleans during the aftermath of Hurricane Katrina. Anderson joined the show in season 3 as Derek Watson, an actor who waits tables to get by.

Treme, one of the most underrated shows of the 2010s, was nominated for six Emmys and included a cast of Melissa Leo, Steve Zahn, and John Goodman over its four seasons.

2 The Departed (2006) – 8.5

Stream On HBO Max

The second best Martin Scorsese film, according to IMDb, the Leonardo DiCaprio-Matt Damon starrer follows two moles (DiCaprio and Damon), one working for the police and the other for the mob, who simultaneously try to infiltrate each other’s organizations.

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Anderson plays Trooper Brown, a character who becomes important during the climax of the movie, and is a friend of DiCaprio’s character. The Departed won Best Picture at the Oscars and included a cast of Jack Nicholson, Mark Wahlberg, Vera Farmiga, and Martin Sheen.

1 The Shield (2002-2008) – 8.7

Stream On Hulu

Set in the fictional Farmington district of Los Angeles, The Shield focuses on the activities of the LAPD’s experimental division, who at best use questionable methods to solve crimes. Anderson plays Antwon Mitchell, a ruthless drug lord who comes up against the division’s officers in seasons 4-6.

The Shield aired on FX for seven seasons, racking up six Emmy nominations, and had a main cast that included Michael Chiklis, Walton Goggins, and Glenn Close during its run.

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