Club Shay Shay – Roy Wood Jr. Part 2 (October 29, 2025)

Host: Shannon Sharpe
Guest: Roy Wood Jr.

Episode Overview

The second part of Roy Wood Jr.’s appearance on Club Shay Shay provides an in-depth, candid journey through his comedic career, personal struggles, and family history. The conversation, hosted by Shannon Sharpe, is raw and humorous, ranging from showbiz anecdotes to reflections on fatherhood, legacy, and resilience. Roy discusses surviving tough breaks in the entertainment industry, navigating early life challenges, the lessons he’s drawn from mentors (and cocaine-wielding coworkers), his mother’s strength, and his forthcoming book, The Man of Many Fathers: Life Lessons Disguised as a Memoir.

Key Discussion Points & Insights

The Comedy Set Environment and Working with Legends (03:19–07:22)

• Roy Wood Jr. shares his approach to being on set:

  • Stays chill and keeps his distance initially to avoid the pitfalls of being "too chummy" and risking his job.
  • Recounts the camaraderie and support from the "Daily Show fraternity" after his tenure ended.
  • Highlights positive experiences with prominent actors, specifically recounting comedy improv with Keanu Reeves for an upcoming movie, Outcome:
    • “Keanu ain’t afraid of you stealing his shine... that’s a big issue on a lot of comedy sets, you’ll have one star... the writer will come up and be like, yeah, don’t do that joke.” (05:27)

• On sharing the spotlight:

  • “Kevin Hart is definitely... he definitely passes the ball in a scene to make sure you shine. Jon Hamm passed the ball.” (06:15)

• Navigating showbiz social scenes and staying out of trouble:

  • Roy avoids party settings where “the cocaine comes out... that’s where probation helped me.” (07:20)
  • “I don’t ride in cars with people. I drive. Or I’ll meet you there. I don’t know what’s in your car.” (08:15)

Early Career Breaks and Industry Setbacks (08:54–13:12)

• Working with Whoopi Goldberg on a sitcom that never aired:

  • Roy describes Whoopi’s skill (“off book for an hour, ain’t never seen no shit like that before in my life, man” (09:08)) and how the show's collapse indirectly led to his spot on The Daily Show.

• On missed opportunities:

  • “All of this can be snatched and taken away from you... nine times out of ten, it’s not even because of something you did...” (12:26)

• Landing the Daily Show:

  • The failed sitcom opened the door for Neil Brennan to call about Trevor Noah’s new Daily Show.

HBCU Experience and Early Hustles (13:49–20:05)

• Choice to attend a HBCU:

  • Inspired by family lineage and black marching band culture in Birmingham, Roy chose FAMU for college: “There’s just culture there, you know?... from a black school system to an HBCU, it just felt no brainer.” (14:14)

• Baseball Dreams and Growing Up Fast:

  • Tried out for FAMU’s baseball team: “Got cut in 30 minutes.” (16:04)
  • Juggled school and 30-hour workweeks as a teen due to family financial struggles and unstable household utilities.
  • “Grew up listening to your mama borrow money from niggas... the only way to keep that from happening is to be able to self-sustain.” (18:15)

• Entrepreneurial/“hustle” streak:

  • “I’d rake leaves... then at night I would go to a house that didn’t have leaves in the yard and pull the leaves out.” (23:26)

Loneliness, Self-Reliance, and Early Standup (20:05–36:19)

• On maturing early and not having a childhood:

  • “No. Not once we moved to Birmingham... But when I really started digging deep on myself, I did this so I wouldn’t be a burden on my mom.” (20:05, 21:50)
  • Used crime as a misguided form of self-reliance: “There’s a degree of excitement to committing crimes... but I did this so I wouldn’t be a burden on my mom.” (20:32, 21:50)

• Differentiating loneliness from being alone:

  • “I think the problem with true loneliness is that you can immediately become so desperate for human contact that you’re willing to do anything, go anywhere, hang with anybody.” (30:16)

• Comedy as a path:

  • Not a class clown in high school, but became known for heckling and cracking jokes from the baseball bench (32:21).
  • Inspired by Ricky Smiley and early standup shows he watched at FAMU and Florida State (33:30).
  • “The first time I saw the power of words just destroy the room, man.” (33:30)

Comedy Career, Influences, and Industry Navigation (36:19–54:53)

• Never quit mindset:

  • “By the time I graduated college, I was three years in it... I never thought about quitting. I’m lucky, man.” (36:27–37:59)

• The Prank Call Era:

  • Grew a viral following from prank call CDs, which were distributed via Black-owned stores and later picked up by mixtape DJs (38:15–42:20).

• Comedic influences:

  • “Sinbad. Chris Rock, George Carlin. Sinbad was just a beast, man.” (43:28)
  • “My early standup was a terrible Martin Lawrence impersonation.” (44:50)

• First big break with D.L. Hughley:

  • Roy fabricates his way into opening as a local radio comic, earns the gig by shining on stage, and gets instant validation from DL, skipping the normal club politics:
    • “DL’s vouch skipped me straight to the front of the fucking line.” (49:49)

• On the grind and self-marketing:

  • Deep respect for Lavell Crawford and Bruce Bruce’s “intentional, diabolical” approach to marketing: going to malls, barbershops, and community events. (51:19–52:51)

Navigating Comedy’s Complex Social Ecosystem (54:53–63:56)

• Stories from the road:

  • Outlining the tough reality of bombing at home and at venues like the Apollo:
    • “I bombed. Ooh, I bombed. And it’s worse when you bomb at the crib...” (62:24)
    • “I got booed, but no sandman. So whatever you wanna call that, right?” (62:49)

• On Cat Williams’ infamous Club Shay Shay appearance:

  • Roy reflects on industry infighting and Kat's candor:
    • “My goal at any comedy show is to leave before the cocaine comes out.” (60:03)
    • “Most of the shit Cat was talking about, the cocaine was out, okay?” (60:03)
    • Both respect Cat’s political and comedic nimbleness: “Cat can just be silly, and then he can be poignant.” (63:56)

• Comedy as journalism:

  • “Comedy is journalism. We’re all reporters. Every comedian you name is a reporter... reporting on the world as they see it or themselves.” (65:37)

From The Daily Show to Self-Mastery (66:27–77:47)

• Making Black stories matter:

  • Trevor Noah gave Roy room to explore complex Black issues in media, such as the Million Man March and Chicago’s gang conflict de-escalators (66:27–69:52).

• Control and independence:

  • Learning from Dave Chappelle’s career (and legacy of self-reliance):
    • “It’s hard to starve a man that can grow his crop and cook for himself. You can’t starve him.” (72:52)

• Industry heartbreaks:

  • Roy recalls being fired over Twitter and overlooked for jobs after being promised advancement:
    • “I got fired from radio. I found out I got fired from radio over Twitter. Damn.” (73:54)
    • “The same as I did after getting fired over Twitter, the same as I did after the handshake sitcom. I’m not scared. Right. Because I’ve slept in fucking bus stations. All I need to do is make sure that the boy got a roof, he got clothes, and he got food.”
    • “Once you accept that you’re completely and unapologetically fucked, only then are you free.” (75:13)

Cautionary Tales and Life Lessons (77:49–97:31)

• Pranking J. Prince – When Jokes Cross Boundaries:

  • Roy nearly learned the hard way that not everyone can be pranked, particularly Houston legend J. Prince:
    • “Where you at? ...We spend the next 20 minutes trying to call J. Prince to, like, make sure shit is cool, right?” (84:24)
    • “I was in Houston a total of three hours. I landed, went to the studio, prank called J. Prince, the shit went sideways, I went to the airport, back in Birmingham...” (86:01)

• Lessons from teenage jobs:

  • A story of snitching on his coworker “Cocaine Mike” at the hospital dish room and the lesson it taught:
    • “If you are exceptionally good at your job, the rules do not apply to you.” (91:02)

Reflections on Family, Legacy & Fatherhood (92:22–102:48)

• Father’s complex legacy:

  • “I didn’t have the best father, but I became a great father. I didn’t have the best examples of love, but I still seek the opportunity to create that construct for my son.” (96:07)

• Discussing his upcoming book:

  • Top three lessons for men:
    1. “It is okay if you didn’t get everything from your dad... I got everything I needed.”
    2. Importance of supportive partners and choosing marriage wisely (per Mary Harman’s advice).
    3. “Regardless of when your father passed, I think we’re all men of many fathers... we are all poured into by innumerable people in our lives.” (97:31–98:19)

• The presence of his late father’s spirit after his passing:

  • “Showed up as a ghost for two weeks straight...I heard him doing was getting ready for work.” (100:05)

• Working with Trevor Noah:

  • Praises Trevor’s mastery of channeling anger constructively:
    • “I’ve never met a black man with a better understanding of what to do with his anger than Trevor Noah... I’m the angry motherfucker from Alabama...But Trevor was very measured and very kind. Still very on the nose, but he knew how to not lead with anger.” (101:27)

Notable Quotes & Memorable Moments

• On surviving showbiz politics:

  • “All of this can be snatched and taken away from you...nine times out of ten, it’s not even because of something you did.” (12:26)

• About his set presence:

  • “I don’t ride in cars with people. I drive. Or I’ll meet you there. I don’t know what’s in your car.” (08:15)

• On comedy as a lens on society:

  • “Comedy is journalism. We’re all reporters. Every comedian you name is a reporter.” (65:37)

• Philosophy after setbacks:

  • “Once you accept that you’re completely and unapologetically fucked, only then are you free to move throughout this country without care and concern.” (75:13)

• On Trevor Noah’s leadership:

  • “I’ve never met a black man with a better understanding of what to do with his anger than Trevor Noah.” (101:27)

• On fatherhood:

  • “I didn’t have the best father, but I became a great father. I didn’t have the best examples of love, but I still seek the opportunity to create that construct for my son.” (96:07)

Timeline of Important Segments

| Timestamp | Segment Description | |-----------|---------------------| | 03:19 | Roy’s set etiquette, working with big names, and the risk of being “too chummy” | | 05:08 | Hilarious improv with Keanu Reeves, respect for collaborative stars | | 08:54 | Story of sitcom with Whoopi Goldberg, learning from canceled projects | | 13:54 | Choosing an HBCU, family legacy, and Birmingham culture | | 16:04 | Baseball tryouts at FAMU, early hustles, and life lessons from adversity | | 21:50 | “I did this so I wouldn’t be a burden on my mom.” Motivation behind early grind | | 36:19 | Never considering quitting comedy; early career grind | | 38:15 | Rise of his prank call CDs and viral success | | 49:49 | D.L. Hughley gives Roy his “big break” in standup | | 60:03 | Comedy, drugs, infighting, and Cat Williams’ industry revelations | | 65:37 | "Comedy is journalism"—on political comedy and self-reflection | | 73:54 | Fired from radio, accepting industry heartbreak | | 84:24 | Pranking J. Prince in Houston—dodging real-world consequences | | 92:57 | Father’s legacy; on being a “nepo baby” and black excellence | | 96:07 | “I didn’t have the best father, but I became a great father.” | | 97:31 | Key lessons from his book for men and fathers | | 101:27 | Reflections on Trevor Noah’s mentorship |

Final Takeaways

Roy Wood Jr. speaks with uncommon candor about the instability of the entertainment business, the need for self-sufficiency, and the importance of mentorship and community. His journey—from a hustling kid in Birmingham to a nationally respected comic, radio prankster, and writer—is rich with lessons about resilience, resourcefulness, and legacy. The humor throughout is real, grounded, and tinged with wisdom earned from setbacks and survival.

Roy’s closing message to men:

• “You got worth, man. You matter. And being present for those kids, that’s important. It’s paramount... we’re all men of many fathers.” (97:31–98:19)

On his own purpose:

• “I look at my son every day, man, and I’m just grateful. I wouldn’t have achieved half I’ve achieved in the last 10 years if not for his presence.” (99:38)

Recommended For

Anyone interested in standup comedy’s inner workings, Black culture and HBCU experiences, stories of grit in the entertainment industry, or personal tales of breaking generational cycles. Roy’s blend of humor, realness, and insight makes this a powerful episode for listeners seeking life lessons with laughs.