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.

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