Since 2016-present: Two Shakes Entertainment and other projects
In early 2018, he made a cameo in the comedy film Super Troopers 2, and later starred in the Epix murder thriller series The Truth About the Harry Quebert Affair. In October of that year, it was announced that Wayans would star in the CBS sitcom Happy Together. The series was canceled after 13 episodes due to low ratings. In November, he launched a production company titled Two Shakes Entertainment. Its first show, the comedy drama Glamorous, was initially ordered by The CW before premiering on Netflix in 2023. In 2019, he guest-starred on the IFC sketch comedy show Sherman's Showcase.
In 2020, he starred in the Netflix romantic comedy film Love, Guaranteed. He also appeared in the CBS anthology series The Twilight Zone, as well as the Netflix animated series Hoops. In 2021, Wayans appeared in five films: the comedy Barb and Star Go to Vista Del Mar, the Apple TV+ crime drama Cherry, the romcom Long Weekend, the Netflix Western The Harder They Fall, and the comedy Supercool. He began hosting the Peacock game show Frogger, based on the video game of the same name. He also appeared in the NBC sitcom Kenan that same year.
Wayans began hosting the NBC game show Raid the Cage in 2023, based on the Israeli television series of the same name. In 2024, he starred alongside his father Damon Wayans on the CBS sitcom Poppa's House, loosely inspired by their real-life relationship. Despite winning an NAACP Image Award for Outstanding Supporting Actor in a Comedy Series for his performance, the series was canceled after its first season. The same year, he appeared in the Apple TV+ show Shrinking as Derrick #2. He was nominated for Outstanding Guest Performance in a Comedy Series at the Black Reel TV Awards for his performance. He also starred in the Netflix romcom Players, and appeared in the Netflix comedy film Kinda Pregnant in 2025.
Wayans will appear in the upcoming horror parody film, Scary Movie, the sixth installment in the Scary Movie franchise. He is set to appear in the CBS comedy Overstepping, which was first announced in November 2024. In February 2026, it was announced that he would lead the NBC drama pilot Puzzled based on the Danielle Trussoni novel The Puzzle Master.
