He is the son of Shirley Richmond.[3] His earliest roles include an appearance in the music video for the 1985 Kool & the Gang song "Cherish" and commercials for fast food chains Burger King and McDonald's.[3]
In 1986, Richmond made his debut as Kenny, also known by the alias Bud, on sitcom The Cosby Show.[4] He made his first appearance in the episode "Theo's Flight", and after appearing occasionally during season 3 Richmond was promoted to a recurring role the following season.[5] Alongside the other child actors on the series, he won the Young Artist Award for Best Young Ensemble Performance in 1989.[6] Richmond would go on to appear in 32 episodes of the show until it ended in 1992.[7]
He played Darren Dixon in the 1993–94 sitcom Getting By with Merlin Santana as his brother Marcus; they had previously appeared together on The Cosby Show.[12][13] In 1997, Richmond began his role as Tamera Campbell's boyfriend Jordan Bennett on the fifth season of the hit series Sister, Sister, and became a regular cast member during its sixth and final season.[14] While acting on Sister, Sister, he earned his second Young Artist Award nomination in 1999.[15]
Richmond starred in Trippin' (1999) as Gregory Reed, a high school senior who tends to daydream instead of focusing on his life.[16] One reviewer claimed Richmond was "great" in the role.[17] In an otherwise negative review, another critic viewed Richmond as "appealing" and that he "worked well" with co-star Maia Campbell.[18]
During the 2000s, Richmond appeared in several films throughout the decade. In Scream 3 (2000), he played Tyson, who is later slain in the film.[19] The following year, Richmond portrayed Malik, a character meant to satirize tokenism,[20] in Not Another Teen Movie.[21] Richmond was Mini Cochran in the 2002 film National Lampoon's Van Wilder,[22] and appeared as Marcus in the independent horror film Hatchet (2007).[23] Richmond portrayed teacher Calvin Babbitt in the short-lived 2006 sitcom Teachers.[24][25]
Richmond acted less frequently in the 2010s. He guest starred in the series finale of Psych in 2014, portraying the boss of Gus.[26] Richmond also appeared in the comedy film FDR: American Badass! (2012) as George.