Sheryl Underwood On Dating Shannon Sharpe, Queens Of Comedy Beef, Mo'Nique, Katt Williams & Skip

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In this candid episode of Club Shay Shay, Shannon Sharpe sits down with comedian, actor, and TV host Sheryl Underwood. Sheryl opens up about her journey in comedy, from working a 9-to-5 while performing late-night gigs to breaking through on Def Comedy Jam. She reflects on the grind it took to succeed, including her groundbreaking role as the first female finalist in the 1999 Miller Lite Comedy Search.

Sheryl and Shannon reminisce about their first meeting in 1993, when Shannon was starstruck by Sheryl’s comedic talent. They laugh about their early friendship and their first date.

Sheryl shares how mentorship from Damon Wayans and her ability to connect with audiences propelled her career. She also discusses balancing adult and clean comedy, inspired by legends like Bernie Mac and Bob Saget, and her mission to unite men and women through relatable humor.

The conversation takes an emotional turn as Sheryl talks about the impact of Monique’s performance in Precious and pivotal career moments, from her Def Comedy Jam debut to overcoming illness during her iconic Showtime at the Apollo performance. She also opens up about the challenges of acting, landing her role in Beauty Shop, and the support of Sherri Shepherd.

Sheryl advocates for more opportunities for comedians like Earthquake and D.L. Hughley to reboot classic sitcoms. She shares stories of working with figures like Master P and Warren Beatty, emphasizing her commitment to authenticity. She also credits Tom Joyner for giving her one of her first radio opportunities and stresses the importance of radio in Black culture. Sheryl highlights the need for more women in leadership roles in media, especially in radio and sports.

Sheryl reflects on her early recognition of Katt Williams' talent and her advocacy for him, alongside her gratitude for mentors like Uncle Luke. She discusses her business acumen, shaped by growing up in an entrepreneurial household, and her responsibility to care for her disabled sister. This sense of duty shaped her work ethic and drive to succeed.

Sheryl also addresses the challenges Black talent faces in entertainment, from fair compensation to systemic barriers. She praises creators like Tyler Perry, Issa Rae, and Regina King for paving the way but acknowledges the ongoing struggle for equity. They discuss how Black culture, especially rap music, is undervalued despite its influence on mainstream media.

The conversation turns personal as Sheryl shares her experiences with respect, survival, and trauma. She opens up about painful moments, including sexual abuse, and the resilience these challenges have built in her. Sheryl stresses the importance of forgiveness, grace, and the healing power of family.

Sheryl discusses her views on love, relationships, and vulnerability, sharing what she desires in a partner and the societal expectations placed on successful women. She reflects on lessons learned from her Southern upbringing and the value of mutual respect in relationships.

With heartfelt anecdotes, Sheryl emphasizes the importance of mentorship, collaboration, and creating opportunities for the next generation of comedians. This episode is a masterclass in resilience, authenticity, and the art of making people laugh through life’s highs and lows.

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About Club Shay Shay:
Club Shay Shay is a weekly podcast hosted by Shannon Sharpe – 3x Super Bowl champion, member of the Pro Football Hall of Fame and co-host of First Take on ESPN. Each week Shannon will sit down with athletes, celebrities and influencers to break down, analyze and discuss the latest headlines in sports, pop culture and everything in-between. Get on the VIP list at Club Shay Shay NOW and never miss an episode!

Sheryl Underwood | EP. 153

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