Hailing from Fayetteville, Georgia, American actorGary Anthony Williamsis a versatile actor with credits in theater, film, television, video games, and a couple of web series. Before Williams’ acting career took off, he started in theater as a member of Atlanta’s longest-running improv troupe, Laughing Matter. Williams would then debut his professional acting career in 1990’s television adaptation of the 1965 novel and 1967 film,In the Heat of the Night.
After moving from Georgia to Los Angeles in 1998, Williams secured television roles in the early to mid-90s before starring in his feature-length film debut, 1994’sRadioland Murders. Williams has displayed his range ever since, as the actor is known for turning in solid performances in dramas, comedies,and various animated projects. We’ll list some of the actor’s most notable roles based on popularity and pop-culture relevance in honor of the actor’s three-decade-long career.
10Harold & Kumar Go to White Castle
Kicking off our list is 2004’s buddy stoner comedyHarold & Kumar Go to White Castle, directed by Danny Leiner and starring John Cho and Kal Penn.White Castlefollows the exploits of two college-aged stoners and their ridiculous quest for a White Castle restaurant. The movie grossed $23.9 million on a $9 million budget and was a success with critics and audiences, thus ensuring a sequel.
White Castlewas notable for its subversion of racial stereotypes and wacky humor and featured many beloved television and film actorsin brilliantly placed cameos. Among these cameos is Williams as Tarik Jackson, a philosophical Black man who shares a jail cell with Harold in one of the movie’s funniest scenes. When Harold inquires about Tarik’s arrest, Tarik tells Harold that his arrest was for “being Black” and that “it happens all the time.” Even though the scene is less than five minutes, Williams’ calm demeanor when the police harass him is hilarious, and the after-credits scene with Tarik and the officers is just as funny.
9Teenage Mutant Ninja Turtles: Out of the Shadows
Teenage Mutant Ninja Turtles: Out of the Shadowswas released to theaters in 2016 to mixed critical reception. The movie received criticism for lacking the charm and wit of the source material in favor of flashy CGI effects and bloated action sequences. Despite the movie’s poor reception, Williams’ portrayal of everyone’s favorite mutant Common warthog Bebop was among the few highlights.
Related:Every Teenage Mutant Ninja Turtles TV Show, Ranked
The dim-witted criminal known as Anton Zeck is one of the victims of Dr. Baxter’s newest experiment and, along with his partner-in-crime Ivan Steranko Owen Rocksteed, also known as the rhinoceros Rocksteady. In the comics, Bebop and Rocksteady are a couple of bumbling buffoons whose criminal exploits are thwarted by the eponymous Teenage Mutant Ninja Turtles. Williams’ portrayal of the beloved criminal has everything from Bebop’s eccentric style to his immediately recognizable laugh.
8Sheriff Callie’s Wild West
Disney Junior’s CGI-animated children’s television showSheriff Callie’s Wild Westdebuted in 2013 and ran for forty-five episodes until its conclusion in 2017. The show centers around an anthropomorphic calico cat named Sheriff Callie and her efforts to maintain peace, happiness, and friendship in the Wild West town of Nice and Friendly Corners. The show was a success, as critics praised the decisionto teach children manners and friendlinessthrough the Wild West aesthetic.
Williams portrays siblings Dusty and Dirty Dan, two mining peccaries who inhabit Nice and Friendly Corners. The episodes featuring the peccaries address selfishness and sharing, two issues siblings commonly struggle with. Williams’ performance meshes well with voice-acting legends such as Kevin Michael Richardson, Cree Summer, and Dee Bradley Baker.
7Boston Legal
2004’s legal dramedyBoston Legalboasted 101 episodes across five seasons and starred James Spader and William Shatner. The Primetime Emmy Award-winning show follows Alan Shore (Spader), a character fromLegal’s predecessor show,The Practice, and his exploits at his new high-end firm in Boston.
Williams plays Clarence Bell, a recent law school graduate and introvert introduced in the show’s third season. Clarence, also known as Clarice, adopts different personas to help manage his shyness around others. Williams’ theater background shines inLegal, as the role of Clarence required him to portray the character’s many personas on a near-constant basis over two seasons.
6Marcus McStuffins
Disney Junior’sDoc McStuffinsis the second CGI-animated educational children’s show on our list, and the show follows Dottie “Doc” McStuffins, a seven-year-old girl who likes fixing and helping her toys. Like her mother, Dr. Maisha McStuffins, Doc wants to be a doctor when she gets older, and she uses her toys to practice on her younger brother Donny and their toys.
Williams plays Doc and Donny’s father, Marcus, a stay-at-home dad who spends a lot of time nurturing and encouraging his daughter to be the best doctor she can be. This role is notable for Williams as it displays hisrange as a voice actor, being able to pitch his voice from nasally high inSheriff Callie’s Wild Westto warm and calming inDoc McStuffins.
5Undercover Brother
Starring Eddie Griffin and former SNL cast member Chris Kattan, Malcolm D. Lee’s satirical spy blaxploitationUndercover Brotherhit theaters in the Summer of 2002 and received generally positive reviews. The 2002 comedy was one of many released during the spoof comedy boom of the early to mid-2000s, and Dave Chappelle, Neil Patrick Harris, Billy Dee Williams, and even the late musical genius James Brown contributed to it. The movie follows Griffin as the titular Undercover Brother as he joins the B.R.O.T.H.E.R.H.O.O.D., a secret, pro-Black organization fighting against the wills of “The Man.”
The B.R.O.T.H.E.R.H.O.O.D.’s membership consists of many pro-Black spies, but Williams’ turn as Smart Brother is among the film’s funniest characters. As his name would suggest, Smart Brother is the B.R.O.T.H.E.R.H.O.O.D.’s authority on all things technology and history-related. Moreover, he briefs Undercover Brother on his missions, supplies him with his gadgets, and is often the voice of reason whenever the members argue.
4Whose Line Is It Anyway?
With 403 episodes and twenty seasons under its belt,Whose Line Is It Anyway?hasbeen on the air since 1989 and doesn’t appear to be slowing down anytime soon.Anywayis the American remake of the British improvisational comedy series of the same name and features the talents of comedians Wayne Brady, Ryan Stiles, and Colin Mochrie. The show’s concept is that its performers act out characters, scenes, and songs predetermined by the host or suggested by audiences. Williams’ involvement with the show since its ninth season was a stroke of genius as the actor tapped into his theater and improv background — this time on the silver screen.
3Moon Girl and Devil Dinosaur
Marvel’sMoon Girl and Devil Dinosaurpremiered in 2023 and centers around Lunella Lafayette, a thirteen-year-old genius who activates a mysterious portaland fights crime with the red T. rex(Devil Dinosaur) that steps out of it. Williams portrays James “Pops” Lafayette Sr., a brilliant inventor and the owner of Roll With It, the show’s roller rink and popular hangout spot. Despite Pops’ age, he possesses youthful energy and wants the best for his offspring. Even in his old age, Pops embodies swagger and charisma, and Williams’ smooth line delivery help cement those characteristics. In addition to his work as Pops, Williams also voices Rockin’ Rudy and Garko the Frog-Man, two small-time villains with less-than-stellar powers and abilities.
2Malcolm in the Middle
FOX’s American sitcomMalcolm in the Middlecenters around the Wilkerson family, a dysfunctional lower-middle-class family, and the exploits surrounding them and their neighbors. The show enjoyed a seven-season run across 151 episodes and won four Primetime Emmy Awards before concluding in 2006. Williams plays Abraham “Abe” Kenarban, a timid and meek man who occasionally shows his firmer side when defending his family and friends.
Related:Where the Malcolm in the Middle Cast Is Today
Father to Malcolm’s best friend Stevie and best friend of Malcolm’s father Hal, Abe is also intelligent, hard-working, and enjoys playing poker with Hal and their friends. Williams’ portrayal of Abe is notable because it goes against the archetypical African-American father typically seen in the media. While Abe is nurturing and warm, he shares many of the same fears as his son and isn’t afraid if others know it. Nevertheless, Abe supports his family with an exceptional income, spends ample time with his son, and supports his friends whenever they need help.
1Uncle Ruckus
Aaron McGruder’s satirical animated seriesThe Boondockspremiered on Adult Swim in November 2005 and was an instant success among viewers. Knownfor its anime-like art style, beautiful animation, sniping critics on society, and uncompromising commentary on the African American Diaspora,The Boondockswas just as controversial as it was successful. The show followed Huey, Riley, Grandad Freeman, and other characters as they navigated living in a primarily White suburban neighborhood and the challenges associated with their upper-middle-class status.
Among the characters featured inThe Boondocks, a particular character stood out among the fan base for his bizarre design, fleshed-out background, and unforgettable voice — and that character is none other than Uncle Ruckus. The glass-eyed, ponytail-wearing older Black man is perhaps best known for his racist views towards other African Americans and his appearances accompanied by the sounds of a tuba. What’s interesting about Uncle Ruckus is the McGruder’s ability to make an otherwise unlikable character somewhat empathetic as we eventually learn he was the product of a brutally harsh upbringing, as seen in the Season 3 episode, “The Color Ruckus.”
Nevertheless, Williams’ gravelly and hilarious performance makes an otherwise detestable character a fan favorite, and despite a live-action Uncle Ruckus movie never materializing, Williams would still go on to play Uncle Ruckus in a series of live-action webisodes to a generally positive reception, thus further cementing the character’s legacy.
