In the latest episode of Club Shay Shay, Shannon Sharpe sits down with the legendary Damon Wayans, a true comedic icon and Hollywood heavyweight.
Damon opens up about his extraordinary upbringing in a large, tight-knit family, revealing the tough love, financial struggles, and sibling dynamics that shaped his path to stardom.
From his rebellious school days to his first foray into stand-up comedy, Damon shares raw and hilarious stories about his life before fame, including his experiences with family discipline, navigating school with a clubfoot, and his early run-ins with comedy as therapy. Damon dives deep into his career, reflecting on his time with In Living Color, the birth of his iconic character “Homie the Clown,” and his battles with the entertainment industry, including his brief stint on SNL and the challenges of working on toxic sets.
He also shares a hilarious encounter with boxing legend Mike Tyson, who once tried to beat him and his brother Keenen up for making fun of him during a comedy bit. He also opens up about the complexities of fame, family, and money, offering his thoughts on relationships with friends, financial success, and the struggles of cancel culture.
Damon shares his admiration for Eddie Murphy, recalling how Murphy’s trailblazing comedy career inspired him, while also addressing the complex relationship between Black comedians and their freedom to express themselves on stage, including the controversial topic of cross-dressing. He goes on to talk about Orlando Brown, who he worked with as a kid. Damon also shares stories about his friendship with basketball legend Michael Jordan and what it’s like to have a friendship with someone as iconic as MJ. He even opens up about the dumbest purchase he ever made, offering a humorous take on the lessons he’s learned about money. As for fame, Damon shares his thoughts on the difficulties that come with it —how it’s hard, painful, and managing relationships with family, friends, and money can be a real challenge. He addresses the impact of cancel culture on his career, admitting it’s made him hesitant to return to stand-up. Damon also reflects on his connection with Katt Williams, sharing insights on working together on My Wife and Kids. He touches on the difficult dynamics of nepotism in Hollywood, working with his family, and how he feels about his son, Damon Wayans Jr., stepping into the comedy spotlight. Damon’s time on My Wife and Kids was a pivotal moment in his career. He talks about making a conscious effort to represent Black families in a positive light. His passion for inclusion shines through as he discusses how important it is to have Black people as a part of his sets and the broader television and film landscape. In this episode, Damon doesn’t shy away from discussing Kanye West, offering a nuanced perspective on Kanye’s current behavior while acknowledging his love and admiration for the artist despite the controversy. With a healthy dose of humor and heart, Damon discusses his personal evolution, from his marriage and divorce to his current health challenges, including living with type 2 diabetes and surviving a brain tumor.
This episode is a celebration of family, resilience, and the hard-earned wisdom that comes with a life well-lived. Damon shares how he now values the beauty of his family and faith more than ever and what he wants his legacy to be.
Tune in for a candid, inspiring, and hilarious conversation with one of comedy’s brightest stars.
