He is best known for his roles as Howard in the sitcom The Cosby Show, Officer Carl McMillan in Mike & Molly, Stan Hill in Good Girls, Wes in The Chronicle (2001–2002), and Detective Tom Selway in Blind Justice (2005).

He is also known for providing character voices in the Transformers film series, and portraying Bailey in She Creature (2001) and Louis Armstrong in Bolden (2019).

His first television role was on the NBC's The Cosby Show, where (on a recurring basis) he portrayed Theo Huxtable's college friend Howard during Seasons 5 and 6 of the series.

He was also a main cast member on the CBS sitcom Mike & Molly (Wilson frequently works with good friend and fellow actor Billy Gardell), and has also acted in Prison Break.

Wilson is known as the voices of Frenzy, Mudflap and Brains in the Transformers film series.