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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Welcome back to Part 2 as Sheryl 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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Shannon Sharpe and Chad “Ochocinco” Johnson react to a wild weekend of AFC and NFC Divisional playoffs. Top stories include the Chicago Bears finalizing a contract with Ben Johnson to be the next HC, Heisman winner Travis Hunter's NFL future could be in Cleveland, time is ticking for Baltimore Ravens QB Lamar Jackson’s Super Bowl hopes and much more!

03:10 - Ben Johnson will be the newest head coach of the Bears
09:41 - Travis Hunter going to the Browns?
12:35 - Ravens vs. Bills
28:47 - How many chances will Lamar Jackson get?
34:46 - What’s the problem in Dallas?
42:10 - Eagles vs. Rams

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Shannon Sharpe and Chad “Ochocinco” Johnson react to a wild weekend of AFC and NFC Divisional playoffs. Top stories include Washington Commanders rookie QB Jayden Daniels carries his team to victory over the top-seeded Detroit Lions, Patrick Mahomes and the Kansas City Chiefs advance to their 7th straight AFC Championship game, Unc says the Dallas Cowboys can't have a culture as long as Jerry Jones is at the helm and much more!

03:14 - Commanders vs. Lions
20:21 - Chiefs vs. Texans
41:44 - Cowboys can’t have culture because of Jerry Jones

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On the Tuesday, January 21 episode of 520 in the Morning, Jeff Teague, DJ Wells, and B Hen react to Ohio State beating Notre Dame in the college football national championship. Ohio State wins their first national championship since 2014, and beats Tennessee, Oregon, Texas, and Notre Dame in the first year of the 12-team playoff. The guys then react to the Boston Celtics blowing out the Golden State Warriors 125-85, and debate whether it’s time for the Warriors to move on from head coach Steve Kerr.

Timeline

2:00 - Ohio State Wins Natty

14:00 - Warriors Lose To celtics

26:00 - Cavaliers Continue To Roll

30:00 - Mavericks Win

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Shannon Sharpe and Chad “Ochocinco” Johnson react to Ohio State defeating Notre Dame in the College football National Championship. Later, Unc & Ocho interview DaMichael Jenkins and his wife to share their story after being racially profiled in viral video outside their Ohio home.

03:19 - Introduction
06:15 - OSU v ND
30:00 - DaMichael Jenkins joins

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Shannon Sharpe and Chad “Ochocinco” Johnson react to the Chicago Bears hiring Detroit Lions OC Ben Johnson as their head coach, Matthew Stafford and Cooper Kupp's uncertain future with the Los Angeles Rams, reports the Cleveland Browns will draft Heisman Trophy winner Travis Hunter in the 2025 NFL Draft, and much more!

03:20 - Ben Johnson agrees to be head coach of the Bears
09:50 - Kupp not sure if he’ll stay with the Rams
24:54 - Ro Sparks read
28:14 - Browns may take Travis Hunter at 2nd overall
32:21 - Jalen Milroe
33:17 - University study on Womens Friendships
43:00 - Q and Ayyyy

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Bubba Dub gets real about the state of America on Martin Luther King Jr Day, Trump’s inauguration, and the ongoing fight against racism. From Ohio State’s national championship win over Notre Dame to Elon Musk stirring up controversy with Nazi symbolism, Bubba Dub breaks it all down with no filter!

He touches on everything from economic struggles, the state of Black unity, and how we can uplift each other while keeping it 100 in the face of challenges. Oh, and you know he’s got to say something about Snoop Dogg switching sides too!

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We’re back with Season 3, Episode 26 of Club 520, where Jeff Teague and the guys debate who would win between Milwaukee Bucks star Giannis Antetokounmpo and Kevin Durant of the Phoenix Suns in a game of 1-on-1. Jeff is adamant that Giannis would be too strong for KD to deal with and would bully him down low. The guys then talk about the best Cinderella championship teams in NBA history and how cool it was for Kawhi Leonard to show up in Toronto, win a title for the Raptors, and leave the next year. Jeff talks about whether Chicago Bulls’ Zach LaVine is a Top 5 shooting guard in the NBA, and much more.

Timeline

3:00 - Mall food

8:30 - Snoop & Trump

30:00 - Jayden Daniels

38:00 - Draymond vs. Poole

56:00 - Zach Lavine

1:04:00 - Scottie Pippen

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On the Monday, January 20 episode of 520 in the Morning, Jeff Teague, DJ Wells, and B Hen react to Jimmy Butler’s return for the Miami Heat after serving his 7 game suspension. The guys talk about whether the time off gave Jimmy and Pat Riley time to clear the air on a path forward with the Heat. The guys then react to the Los Angeles Clipper beating LeBron James and the Los Angeles Lakers, Giannis going off against the Philadelphia 76ers, Nikola Jokic’s triple double, as well as recap the NFL Playoff games from this past weekend.

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Shannon Sharpe and Chad “Ochocinco” Johnson react to Josh Allen and the Buffalo Bills fending off a late run by Lamar Jackson and the Baltimore Ravens after TE Mark Andrews drops the potential game-tying 2-point conversion. Later, Unc and Ocho discuss Philadelphia Eagles RB Saquon Barkley having an explosive game against Matthew Stafford and the Los Angeles Rams to advance to the NFC Championship Game for the second time in three years, Unc wants Lamar to get at least one Super Bowl to solidify his legacy and much more!

03:20 - Show start
04:00 - Intro
05:42 - Ravens v Bills
50:10 - Eagles v Rams

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