Wayans made his film debut in 1994 when he was cast in his father's feature film, Blankman, playing Young Kevin. He later appeared on his father's sitcom My Wife and Kids as John, one of Junior's friends. He later worked as a staff writer on the series.
Wayans began performing stand-up under the pseudonym Kyle Green, in an attempt to establish an identity separate from his family.[5][6] In 2006, he appeared in and served as a writer on The Underground under his real name.[7] Wayans also surprised audiences when he garnered a standing ovation during his debut appearance on Def Comedy Jam.[8] He starred in the Wayans family comedy Dance Flick as the film's main character, Thomas. In 2010, he appeared in the Adam McKay comedy film The Other Guys.[9]
From April 2011 to May 2013, Wayans starred as Brad Williams, one of the lead characters in the ABC comedy series Happy Endings, for which he was nominated for a Critics Choice Television Award and two NAACP Image Awards. Despite critical acclaim and a cult following, the show was cancelled by ABC after concluding its third season.
On May 16, 2011, the Fox Network announced that it had picked up the Zooey Deschanel-anchored comedy New Girl, which featured Wayans in the supporting role of Coach. However, Happy Endings had already been picked up for a second season on rival network ABC. The producers of New Girl initially planned to recast Wayans' role, but later decided not to recast nor reshoot the pilot episode in which he appeared.[10] Instead, starting with the second episode, Wayans' character was substituted with Lamorne Morris, playing the role of Winston.[11]
With Happy Endings cancelled after its third season, it was announced in July 2013 that Wayans would return for at least four episodes of New Girl in the upcoming third season.[12] In November 2013, it was announced that Wayans would remain on the show for the rest of season 3.[13] In May 2014, it was announced Wayans would return as a series regular for season four.
Since 2016: Two Shakes Entertainment and other projects
In early 2018, he made a cameo in the comedy film Super Troopers 2,[18] and later starred in the Epix murder thriller series The Truth About the Harry Quebert Affair.[19] In October of that year, it was announced that Wayans would star in the CBS sitcom Happy Together.[20] The series was canceled after 13 episodes due to low ratings. In November, he launched a production company titled Two Shakes Entertainment.[21] Its first show, the comedy drama Glamorous, was initially ordered by The CW before premiering on Netflix in 2023.[22] In 2019, he guest-starred on the IFC sketch comedy show Sherman's Showcase.[23]
Wayans will appear in the upcoming horror parody film, Scary Movie, the sixth installment in the Scary Movie franchise.[40] He is set to appear in the CBS comedy Overstepping, which was first announced in November 2024.[41] In February 2026, it was announced that he would lead the NBC drama pilot Puzzled based on the Danielle Trussoni novel The Puzzle Master.[42]
Personal life
Wayans has six children. He has two daughters with high school ex-girlfriend Aja Metoyer. He has four children with his current wife Samara Saraiva: two daughters and two sons. They also have one granddaughter named Itali, from daughter Berlyn Wayans and her high school ex-boyfriend, Mike Price.[43]