Damon Wayans Sr. Breaks Silence On Pulling 'The Jackson 5' With His Nephew's Ex-Girlfriend

Damon Wayans Sr. got entangled in a family love triangle in his past dating life!

The comedian admitted to going out with his nephew's former romantic partner after he separated from his ex-wife, Lisa Thorner.

Damon Wayans Sr. comes from a tight-knit family known for their creative collaborations. His brother, Keenen Ivory Wayans created the iconic sketch show "In Living Color," featuring Damon and other siblings.

During an appearance on the Club Shay Shay podcast with Shannon Sharpe, Damon shared a surprising confession: he once dated his nephew's ex-girlfriend. At 64, he reflected on the relationship, admitting, "I was in love with her." 

He also humorously referenced the Jackson family dynamics, likening his situation to Jermaine Jackson marrying Randy Jackson's ex-girlfriend. In his words, "You ain't never done the Jackson 5?"

When Sharpe questioned the appropriateness of the relationship, Damon clarified that his nephew and the woman were not in love. The relationship began around 2001, after Damon's divorce from Lisa.

He recounted feeling an instant attraction to her, saying, "I saw her and I was just like, 'Oh my God. I'm in love,'" only to discover afterward that she had previously dated his nephew.

Damon shared more insights about the romantic endeavor and dived into the dynamic of working with his family. He revealed that he sought his nephew's blessing before pursuing a relationship with a woman he was interested in.

The comedian also humorously noted that family gatherings can become awkward under such circumstances. The Wayans family is known for their collaborative spirit in the entertainment industry.

Currently, Damon stars in the CBS show "Poppa's House," alongside his son, Damon Wayans Jr., and has family involvement from his brother Marlon and sister Kim, who directed an episode. 

In discussing the appeal of working with family with PEOPLE, Damon emphasized that the inherent chemistry and trust they share is something most actors take years to develop, making their collaborations seamless and natural.

Despite his notable appearances in various films and TV specials, the 64-year-old comedian prioritizes stand-up comedy and frequently tours as a stand-up comic.

He is also recognized as a talented writer, director, and producer, with credits including "The Last Boy Scout," "Mo'Money," "Blankman," and "Bamboozled."

In 2022, The Blast shared that CBS was developing a father-and-son comedy that featured the duo, with the script co-written by Damon Sr. and producer Kevin Hench. Although the project was untitled back then, it had reportedly been developing for a while. 

The storyline focuses on "Poppa," a happy-go-lucky talk radio host who must help his adult son transition into full adulthood before he turns 40. The older Wayans will portray Poppa, while Damon Jr. will play the son, who, despite sharing his father's charm, lacks his drive.

This project will be produced by CBS Studios and executive produced by the Wayans men and Hench. It is noteworthy that CBS has been the home for the younger Wayans' Two Shakes Entertainment since its inception.

Damon Jr. began his television acting career with a notable recurring role before landing leading roles in popular series such as "Happy Endings," "New Girl," and the CBS sitcom "Happy Together."

Although "Happy Together" only ran for one season, it featured an episode titled "Like Father, Like Son," which showcased the dynamic between the Wayans men on screen. 

His other popular projects include his father's Showtime sketch comedy series "The Underground" and films like "Supercool," "Cherry," and "Barb and Star Go to Vista Del Mar." Recently, he wrapped up work on the Netflix series "Players" and is also an executive producer for the drama "Glamorous."

His father, Damon Sr., is a four-time Emmy nominee known for co-creating and starring in the groundbreaking series "In Living Color," which marked a pivotal moment in his career.

He is also recognized for his role as Roger Murtaugh in the "Lethal Weapon" franchise and was set to appear back then alongside Pam Grier in the upcoming Tubi thriller "Cinnamon."

Damon Sr. publicly supported Chappelle amid the backlash he faced for his jokes in the Netflix special "Closer," which some considered transphobic. 

In an interview, Damon Sr. praised Chappelle for empowering comedians to express themselves freely, likening his influence to an artist who makes significant sacrifices for their craft, such as Van Gogh. 

Chappelle's material included anecdotes about a transgender friend and jokes that touched on the limitations of transgender experiences, such as the ability to have children.

Damon characterized Chappelle's willingness to address controversial topics as a brave act that could inspire other comedians to share their authentic voices. 

He emphasized the need for a broader conversation about the constraints that comedians often face due to political correctness and the fear of being canceled for their words.

That was quite the revelation from Damon Wayans Sr. and his interesting family!