Comedy legend Damon Wayans took a trip down memory lane on the latest episode of Club Shay Shay, sitting down with Shannon Sharpe for an unfiltered conversation about his storied career, family legacy, and the challenges that come with fame.
Wayans, one of 10 siblings in the famed Wayans family, opened up about his tough yet loving upbringing, detailing the financial hardships and strict discipline that shaped his path to stardom. From his early school days—navigating life with a clubfoot—to discovering stand-up as a form of therapy, Wayans shared both raw and hilarious stories about his journey before making it big.
The conversation shifted to In Living Color, the groundbreaking sketch show that launched his career. Wayans recalled the origins of his iconic “Homie the Clown” character and the behind-the-scenes struggles he faced in Hollywood, including a short-lived run on SNL and the difficulties of working in toxic environments. He even shared a wild story about Mike Tyson attempting to fight him and his brother Keenen after they poked fun at the boxing champ in a comedy sketch.
Beyond comedy, Wayans offered his thoughts on cancel culture, revealing how it has made him hesitant to return to stand-up. He also reflected on the freedom (or lack thereof) that Black comedians have on stage and addressed the long-debated topic of cross-dressing in comedy.
Sharpe and Wayans also delved into his Hollywood connections, including his friendship with Michael Jordan and the dynamics of working alongside family. He touched on nepotism in the industry and how he feels about his son, Damon Wayans Jr., carving out his own path in entertainment. Additionally, he shared memories of working with a young Orlando Brown and insights from his time alongside Katt Williams on My Wife and Kids, where he made a conscious effort to portray Black families in a positive light.
Money was another hot topic. Wayans humorously recalled the dumbest purchase he ever made and discussed the complexities of managing finances in Hollywood. He also spoke about the highs and lows of fame, admitting that navigating relationships with family, friends, and money hasn’t always been easy.
The conversation took a personal turn as Wayans opened up about his health challenges, including living with type 2 diabetes and surviving a brain tumor. Through it all, he shared how his perspective has shifted, emphasizing the importance of family, faith, and leaving behind a meaningful legacy.
Before wrapping up, Wayans offered a nuanced take on Kanye West, acknowledging both his admiration for the artist and the controversies surrounding him.
Packed with humor, wisdom, and heartfelt moments, this episode of Club Shay Shay is a must-watch for comedy fans and anyone looking for an inside look at the life of one of Hollywood’s most influential funnymen.
