Damon Wayans Sr. got entangled in a family love triangle ... Chappelle's material included anecdotes about a transgender friend and jokes that touched on the limitations of transgender experiences ...

And while Damon Sr. was happy in love ... "There was absolutely no hesitation at all [in my voice]," Robert recalled to The New York Times Style Magazine in a December 2024 interview.

Damon Wayans Sr. has detailed his “awkward” family gatherings after he fell in love with his nephew’s ex-girlfriend. The “My Wife and Kids” alum, 64, revealed the dating oversight during ...

Damon Wayans Sr. is far from being the last Boy Scout. After the “My Wife and Kids” star, 64, admitted to dating his nephew’s former girlfriend after his 2000 split from ex-wife Lisa ...

Damon Wayans Sr.’s admittance that he once dated his unidentified nephew’s ex-girlfriend went viral after Shannon Sharpe’s “Club Shay Shay” podcast aired. In the aftermath of Wayans ...

Damon Wayans Sr. opened up about dating his nephew’s ex and how it all started with a post-divorce crush that turned into something deeper. The 64-year-old comedian and actor confirmed the long ...

At such a critical moment in US history, we need reporters on the ground ... I mean, for a family member, that’s off limits, Damon,” Sharpe replied. Damon Wayans photographed in 2025 (Getty ...

Damon Wayans Sr. found a way to make family gatherings an “awkward” affair. The comedian recently admitted to “Club Shay Shay” listeners that he once dated his nephew’s ex-girlfriend.

Sonja Flemming/CBS via Getty Damon Wayans Sr. likes to keep things in the family — in more ways than one. While appearing on the April 2 episode of the Club Shay Shay podcast hosted by former ...

Damon Wayans Sr.’s decades-long career has yielded many interesting stories, with a majority of them having to do with members of his large family. The veteran actor recently spoke about a ...