Club Shay Shay - Roy Wood Jr. Part 1
Club Shay Shay29 Okt 2025

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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Episoder(2262)

Dwyane Wade

Dwyane Wade

NBA legend, 3-time Champion and soon-to-be Hall of Famer Dwyane Wade is here inside Club Shay Shay for an all-encompassing conversation with Shannon. The Miami Heat great sits down and dishes out the behind the scenes stories from his illustrious career in the NBA, what led to his success, and perspective on the game today. From playing with LeBron, to this year's Miami Heat featuring Jimmy Butler, you'll want to hear all that Wade shares in this wide-ranging interview. Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

12 Jun 20232h 11min

Jacquees

Jacquees

Shannon welcomes in Jacquees into Club Shay Shay! The two Georgia natives chat about how the self-proclaimed "King of R&B" reached fame in the music industry, working with several big names and eventually signing with Cash Money Records. Hear him tell stories involving Gunna, Torey Lanez and many other artists! Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

5 Jun 20231h 23min

Ne-Yo

Ne-Yo

Ne-Yo joins Shannon this week inside Club Shay Shay, with the 3-time Grammy Award winner sharing stories about his beginnings, reaching stardom and how the music industry has evolved. Ne-Yo tells Shannon about all of his famous partnerships and collaborations, and what the future holds for the singer and songwriter. Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

29 Mai 20231h 5min

Tabitha Brown

Tabitha Brown

Shannon welcomes in Tabitha Brown to Club Shay Shay this week, where the social media personality and actress tries to convert Shannon to veganism! Hear from Tabitha as she details her rise to fame, and the kinds of messages she delivers to her millions of followers every day. Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

22 Mai 20231h 30min

Timbaland

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Timbaland joins Shannon inside Club Shay Shay this week, where the artist and producer shares stories and lessons taught to him from artists all across the music industry. Listen in as Shannon and the four-time Grammy winner go over his career — working and learning from popular names such as Missy Elliott, Drake, Jay-Z and many others. Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

15 Mai 20231h 20min

Omarion

Omarion

Joining Shannon inside Club Shay Shay this week is R&B singer, actor and dancer Omarion! From his days in B2K to appearing in numerous films, he talks with Shannon about his career and personal life. Hear from the chart-topping artist on how he got his start, and the thought processes behind the biggest decisions he's made in his career. Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

8 Mai 20231h 22min

REWIND: DC Young Fly on his comedic process

REWIND: DC Young Fly on his comedic process

In this special rewind episode of Club Shay Shay, revisit some of Shannon's favorite segments from the show so far. Today, listen to Shannon talk with actor, writer, comedian and musician DC Young Fly about his comedic process, performing live and the modern state of comedy. Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

1 Mai 202320min

Steve Harvey

Steve Harvey

Steve Harvey is here in the club! The comedian, actor and host of Family Feud sits down with Shannon for a wide-ranging conversation on his career, family and tells some incredible stories. It's a conversation not to be missed! Learn more about your ad choices. Visit megaphone.fm/adchoicesSee omnystudio.com/listener for privacy information.

24 Apr 20232h

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