Made acting debut in brother Keenan Ivory Wayans' feature "I'm Gonna Get You Sucka"

Began as rapmaster SW-1 on Fox's "In Living Color" and later became a featured performer

Appeared as Robo in episode of ABC's "MacGyver"

Guest-starred in episode of ABC's "Hangin' with Mr. Cooper"

Consultant, co-creator (with brother Marlon) and star of The WB sitcom "The Wayan Bros."

Co-wrote and co-executive produced with brother Marlon the feature "Don't Be a Menace to South Central While Drinking Your Juice in the Hood", a parody of "hood" movies of the 1990s; brother Keenan also acted in film

Provided the voice of Toof on The WB's animated children's series "Waynehead", based on brother Damon's real-life childhood experiences

Co-wrote and co-starred in "Scary Movie"

Returned to co-star with brother Marlon in "Scary Movie 2"

Co-wrote and starred with brother Marlon Wayans as FBI agents that go undercover as hotel heiresses in "White Chicks" directed by brother Keenen Ivory Wayans

With brothers Keenen and Marlon created, "Thugaboo," (Nickelodeon) a series of animated children's shows that follows the misadventures of nine kids growing up in the inner city

Co-wrote and co-starred with brother Marlon in the comedy, "The Little Man"; directed by brother Keenen Ivory Wayans