Club Shay Shay - Roy Wood Jr. Part 1

Club Shay Shay - Roy Wood Jr. Part 1

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Roy Wood Jr. — comedian, writer, and one of the sharpest political voices in comedy — joins Club Shay Shay for a raw and insightful conversation about free speech, family, and finding truth in laughter.

Roy starts by looking back at his time at CNN, where he was invited to join New Year’s Eve Live with Anderson Cooper and Andy Cohen. He explains why he turned down drinking on-air, knowing that one wrong moment could jeopardize his role. That experience taught him early on how delicate free expression can be in corporate media.

From there, Roy dives into the fallout surrounding Don Lemon’s firing after his controversial remarks about Nikki Haley. He admits that moment reshaped how he viewed the tension between truth and image inside the news world. Hosting CNN’s I Got News for You only reinforced that lesson — showing him that journalism, unlike comedy, often filters honesty through politics and brand management.

Roy recalls one of the toughest breaks of his career — the cancellation of his sitcom pilot with Whoopi Goldberg. He describes how the loss initially crushed him, but ultimately became a turning point. Whoopi’s encouragement reminded him to keep pushing forward, and he returned to stand-up with a renewed sense of purpose and creative control.

He also reflects on how late-night shows like Jimmy Kimmel Live! have become one of the few remaining spaces where comedians can still tackle uncomfortable truths. To Roy, comedy has always been about exposing what people are afraid to say — a mission that’s becoming harder as networks and audiences grow more cautious.

In a more personal moment, Roy opens up about fatherhood and how becoming a dad changed the way he sees his career. He talks about balancing his work on The Daily Show with raising his son, making sure he’s present while showing him the value of purpose and patience. Roy admits that being a father keeps him grounded — it’s what motivates him to stay authentic, to build something that lasts beyond applause.

As the conversation unfolds, Roy praises comedians like Trevor Wallace for using digital platforms to shape the next era of stand-up and Katt Williams for his unapologetic honesty. He also gives love to Marlon Wayans for his versatility and ability to evolve without compromising authenticity. Roy explains that whether it’s political satire or social storytelling, comedy’s greatest power is still connection — making people feel seen through laughter. Roy Wood Jr. shows why he’s one of comedy’s most essential voices. Honest, fearless, and deeply human, he delivers a masterclass in turning truth into humor — and proving that integrity will always be funny.

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Chris Bosh

Chris Bosh

Episode 4 of Club Shay Shay features two-time NBA Champion, 11-Time All Star and Olympic Gold Medal winner Chris Bosh.  In an insightful and wide-ranging conversation, Shannon and Chris discuss Chris pursuing a career in music after his retirement from the NBA, producing a track for Gucci Mane, his musical influences, the relationship between hip-hop and the NBA, and much more. Chris also revisits his illustrious basketball career: playing against Kendrick Perkins in high school, attending Georgia Tech under Paul Hewitt, being drafted in the same ’03 class as LeBron James, Carmelo Anthony and Dwayne Wade, becoming an All Star in Toronto, forming the Big 3 and winning two Finals in Miami. He also discusses his 2008 Olympics run & defending against the Lakers in Kobe’s infamous 81-point game. No aspect of Chris’s storied basketball career and burgeoning musical career is left untouched in this captivating and compelling interview.#DoSomethinB4TwoSomethin & Follow Club Shay Shay:                                                                 https://www.instagram.com/clubshayshayhttps://twitter.com/clubshayshayhttps://www.facebook.com/clubshayshayhttps://www.youtube.com/c/clubshayshay Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

12 Okt 20201h 29min

Snoop Dogg

Snoop Dogg

In Episode 3, Shannon welcomes Snoop Dogg — rap icon, actor, entrepreneur, LA Laker superfan and close friend — to Club Shay Shay.Shannon’s conversation with Snoop touches on a wide range of issues: from the protests in support of racial justice taking place across the country to how Snoop’s early music touched on many of the issues being discussed today. Shannon and Snoop take a look back at some of the stories that defined the rap mogul’s illustrious career, peeling back the curtain to working with 2Pac, Dr. Dre and the other artists with which he’s collaborated throughout his longstanding career. Snoop reveals his 5 favorite hip-hop albums of all time, plus his personal favorite LP from his own discography. He also delves into his acting career, including his role alongside Denzel Washington in ‘Training Day.’Snoop breaks down all the headlines surrounding the Lakers and Clippers, as well as what’s going on in the NFL. He also talks about starting the Snoop Youth Football League, and the many success stories that have come from it.#DoSomethinB4TwoSomethin & Follow Club Shay Shay:                                                                 https://www.instagram.com/clubshayshayhttps://twitter.com/clubshayshayhttps://www.facebook.com/clubshayshayhttps://www.youtube.com/c/clubshayshay Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

5 Okt 20201h 11min

Floyd Mayweather Jr.

Floyd Mayweather Jr.

Episode 2 of Club Shay Shay features Shannon's first ever taped conversation with boxing legend Floyd Mayweather Jr.Shannon & Floyd delve deep into Floyd’s historic 50-0 boxing career, from his 1996 Olympic Bronze medal to his 2017 win over Conor McGregor, and the fights along the way that led him to become “arguably the most accomplished boxer of all time.”Floyd discusses the struggles he faced growing up in poverty, and how his drive and will to win in the face of adversity and racial injustice led him to greatness.  He also touches on how starting his own promotional company helped him achieve independent financial success, his personal and professional relationships with his father, Floyd Mayweather Sr., his favorite boxers of all time, how he would have fought Sugar Ray Leonard, and much more.#DoSomethinB4TwoSomethin & Follow Club Shay Shay:                                                                 https://www.instagram.com/clubshayshayhttps://twitter.com/clubshayshayhttps://www.facebook.com/clubshayshayhttps://www.youtube.com/c/clubshayshay Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

29 Sep 20201h 29min

Sterling Sharpe

Sterling Sharpe

Club Shay Shay is officially open! The Hall of Famer takes it back to where it all began, as he welcomes in his brother & “father figure” Sterling Sharpe  — the first time the two former NFL stars have had a sit-down interview together. Episode 1 of Club Shay Shay is the definitive history of Shannon and Sterling’s upbringing, as well their respective journeys to prominence.Shannon, 52, and Sterling, 55, grew up in a rural area in South Georgia, in a 1000 square-foot cinder block house, with no running water and a thin, leaky, tin roof. The two brothers discuss growing up together with their older sister, Libby, and their influential grandparents, Barney and Mary Porter.Sterling and Shannon detail their college careers and they both tell their sides of the 1990 NFL Draft, when Shannon was selected by the Denver Broncos in the 7th round (192nd overall). Sterling, the 7th overall pick of the 1988 NFL Draft, played at South Carolina before being drafted by Packers. The 5-time Pro Bowler and 3-time All-Pro played 7 seasons in Green Bay. The two brothers delve into Sterling’s playing days, including his career-ending injury and its aftermath. #DoSomethinB4TwoSomethin & Follow Club Shay Shay:                                                                                             https://www.instagram.com/clubshayshayhttps://twitter.com/clubshayshayhttps://www.facebook.com/clubshayshayhttps://www.youtube.com/c/clubshayshay Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

22 Sep 20201h 19min

Welcome to Club Shay Shay

Welcome to 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 Undisputed on FS1. 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!Follow Club Shay Shay:https://www.instagram.com/clubshayshay/https://twitter.com/clubshayshayhttps://www.facebook.com/clubshayshayhttps://www.youtube.com/c/clubshayshay Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

16 Sep 202044s

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