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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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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!
Roy Wood Jr. I Ep. 187
hhttps://youtu.be/r0ISX_IArrY
Club Shay Shay
https://www.youtube.com/c/ClubShayShay
source
- Actor
- American Politics
- Andy Cohen
- black comedy
- Club Shay Shay
- CNN
- Comedy and Politics
- Comedy Central
- Comedy Evolution
- Comedy Icons
- Corporate Media
- Cultural Commentary
- Don Lemon
- Entertainment Industry
- Free Speech
- Jimmy Kimmel
- Kamela Harris
- Katt Williams
- kattwilliams
- Late Night Comedy
- Marlon Wayans
- Media Censorship
- Political Comedy
- Roy Wood Jr.
- roywoodjr
- Shannon Sharpe
- Social Commentary
- Sports
- Stand-up Comedy
- The Daily Show
- Trevor Wallace
- TV News
- Whoopi Goldberg
I believe along with mental health issues, many mass shooters, specifically younger ones are looking for recognition and are copy cats. The media has been responsible not only news outlets, authors and tv show producers as well. And of course the availability of firearms which is not the case in many other developed nations.
Trumps true power base that he holds to is the Heritage Foundation. Heritage Foundation are the ones funding him and are the author's of Project 2025. Heritage Foundation is the final boss in this.
Roy Woods Jr is a breath of fresh air, especially to this show. I appreciate his insight on the topics discussed.
This one was it.
Mannnnn. Roy get that YouTube channel up! Want too see you win!🫡
When a Veep runs for top dog the gloves come off and they take the heat for any of their boss's ideas /policies or foibles. The heat that Kamala took was certainly turned up due to her being a person of color and a female. Not to mention the flames of hate and bigotry faned by tRump & maga.
Nothing like a well versed bruvah‼️💯‼️
Shannon Sharpe is quickly becoming one of the best interviewers of our time.
Roy Wood Jr and Ali Saddiq are 2 of my favorites. This was a great interview! 👏🏾
Shanon does a great interview!
I've seen this guy face on TV
Before. Never had a interest.
Those stimulus checks weren't life changing. It's not like each American got $10 k or better.
Long distance calls were clutch….
This was a good interview. Makes me glad that I support NPR, college radio and independent media.
Glad Roy is receiving his flowers; came from the interview with Trevor Noah (super vulnerable interview) to this one. Great stuff. Now we need you back on The Right Time to talk about the MLB.
I hope that more people watch this episode. It is really good and informative.
I’m so glad he brought up “Funk It”
Excellent interview!!! Music n More, mannn whatttt!!! The old days
On probation you're wired, you're the puppet and they pull the strings, if you find yourself in that situation, do your time and walk out free
Great conversation
Roywood is the Only one to make Trevor Noah look like a quest on the show because if they gave Roywood the Platform it would still be alive today other than the entirely white scripted audience and the clearly monetized / bought off likes to purvey a successful channel when Nobody's watching it in real life.
Love Roy Wood Jr!!!
wow parole officers sound awful
Very good interview. You know a famous millionaire has the same thoughts and fears
2:35:50 RIP PATREEKY
This is a great interview on politics, comedy and life.
There is 37 trillion dollars in home equity in this country, Donald wants that, in Florida they're forcing every home owner to buy flood insurance if they live in a flood plane or not, they'll be offering home equity loans to help home owners cover the cost🤪 there's going to be a blood bath in Florida, you rich ppl can buy up those properties for pennies on the Dollar
2:55:00 Shay has good improv skills. That was a solid and respectful firing. 😅
One of the best interviews I've seen in a long time. This was incredible. Roy is soooo articulate and clear with his thoughts and Shannon has some great questions. And also just lets Roy talk and it was amazing. Such a great interview. Listened to the whole thing in one day.
Love the content from this one! And I plan on getting his book!
12:33 What values are you suggesting we compromise on?
Regarding media censorship, do we just forget about the censorship during COVID!!!!!????? Also, Don Lemon was lying and was putting out information that had no factual context. That's not journalism
I voted for my BEST INTERESTS!!!!!!!!
I disagree about the lie and sticking with it. White people believe that the lesser people will be destroyed during Trump's term and they will survive and everything will be great.
Don' screwed himself
Shannon… Bulls in 🖐🏿
Wow man I fully enjoyed this interview for beginning to end. I felt like I could relate to some of Roy's experiences and I look forward to reading his new book and watching his next special.
Hey did Shannon ask Roy about his lineup yet?
Don't you ever questioned a master lol