Roy Wood Jr. On Bombing at The Apollo & How Failure Fueled His Success | Glass Half Full With Craig Melvin

Summary

Podcast Summary: Glass Half Full with Craig Melvin Episode: Roy Wood Jr. On Bombing at The Apollo & How Failure Fueled His Success Date: May 5, 2026

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Episode Overview

Craig Melvin sits down with comedian, writer, and former The Daily Show correspondent Roy Wood Jr. for a deeply personal, candid conversation about the moments that shape us—especially the hardest ones. From being fired on Twitter and bombing at the Apollo, to navigating complicated family dynamics and embracing the lessons hidden in setbacks, Roy reflects on how adversity fueled his growth both professionally and as a father. With humor and vulnerability, this episode explores how facing fear and failure head-on can become the foundation for lasting success.

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Key Discussion Points & Insights

Facing Defining Moments and the Power of Failure

• Roy shares that his most transformative moments were often low points, not career highlights. He recounts several pivotal setbacks, such as:
  • Getting fired over Twitter from his longtime radio job at a Birmingham station ([03:24-06:49])
  • Auditioning unsuccessfully for The Daily Show in 2007-08 before eventually earning a spot ([07:54-09:23])
  • Leaving The Daily Show because of uncertainty around the host transition ([12:00-14:49])

Quote:
"My life has just been a series of moments of just jumping into the fog without a parachute... The moments where growth came in my career, they were not moments where everything was being wonderful and celebrated and beautiful. They were moments where I was most scared, but also most courageous."
— Roy Wood Jr. [03:24]

Resilience and Jumping Into the Fog

• Roy and Craig discuss career transitions, the uncertainty of show business, and what it means to take risks.
• Roy explains his decision to leave The Daily Show amid host ambiguity, mergers, and industry shifts, emphasizing the importance of knowing when to move on and create new opportunities ([12:00-14:49]).

Quote:
"You're asking me to stay around with all of these different variables? No... This is the best time to make myself available for some other opportunity. I'ma jump into the fog."
— Roy Wood Jr. [14:25]

Evolving Landscape of Political Satire and "Shameless Society"

• The pair reflect on the changing impact of political satire, noting how public shamelessness dilutes the satire’s power ([16:31-17:13]).

Quote:
"Political satire used to have the weapon of shame... We have a shameless society. You can't embarrass people anymore."
— Roy Wood Jr. [16:31]

Family, Fatherhood, and Breaking Generational Cycles

• Roy opens up about his childhood, his complicated relationship with his father—a celebrated journalist—and reconciling his personal experiences versus public perception ([18:41-24:34]).
  • The impact of parental absence and inconsistency.
  • The emotions triggered by hearing others celebrate his father’s legacy, feeling the lack of connection himself.
  • Discovering the root of his father’s struggles through genealogy and "Finding Your Roots."
• Craig relates with his own family history, reflecting the importance of widening perspective and understanding generational trauma.

Quote:
"People think they're telling you that to make you feel good, but it's pissing you off because you're just getting more and more accounts of just how good he was to other people. But he fell short with you."
— Roy Wood Jr. [21:01]

• Roy discusses the resolve to break this cycle for his own son, emphasizing transparency and communication even as a busy entertainer and father.
• His drive and work ethic are directly linked to family hardship: starting to work at 15 to help keep the lights on at home, which instilled the hustle and adaptability he credits for his success ([26:14-31:50]).

Quote:
"I don't want to die early, Craig, and my son's account of me is good stories from strangers. So let me tell you who I am... Some of that is your granddad. But a lot of it is people that—I’m just grateful that God put me in their orbit. And that's the book."
— Roy Wood Jr. [26:31]

The Blessing of Adversity

• Roy and Craig discuss how tough childhoods build resilience, humor, and ingenuity—how adversity made them who they are ([28:28-29:23]).

Quote:
"That tenacity was birthed from a need to survive. And I'm not gonna sit here and act like I had the craziest, most, toughest, most poverty Ghost Face Killer... But also, there's an emotional trauma that comes with that."
— Roy Wood Jr. [29:09]

Bombing at the Apollo & Lessons from Failure

• In the “Craig’s Curiosities” segment, Roy shares a vivid account of bombing at the legendary Apollo Theater—a formative failure, not just career embarrassment, but a lesson in humility and growth ([32:17-37:50]).
  • Describes the unique, intimidating setup of the venue and the physical sensation leading up to being booed.
  • Emphasizes that the pain of failure is necessary and shapes future success.

Quote:
"You can't run from failure... Learn from it. Base yourself in it, man."
— Roy Wood Jr. [36:26]

On Parenting, Being Present, and Chasing Perfection

• Both discuss the tension between career ambition and being present as fathers ([38:36-40:16]).
  • Roy is candid about the guilt of being away, trying to maximize quality time, and constantly questioning if it’s enough.

Quote:
"The idea that I can lay down and go, all right, I did a good job today, because I feel like you have work, you have parenting, and you have rest and recreation. I feel like you can only pick two of those a day to be good at."
— Roy Wood Jr. [38:40]

Legacy, Community, and Giving Back

• Roy hopes to be remembered for supporting his college, city, and state (Florida A&M, Birmingham, Alabama), and his efforts to give back, particularly in youth literacy and sports programs ([40:20-41:43]).

Quote:
"I'm lucky bro... I'm very lucky to make it out of a place where a lot of folks don't make it out of... and I hope that my body of work will show that all three of those things were the truth."
— Roy Wood Jr. [41:14]

Glass Half Full or Half Empty?

• Roy quickly says he views life as "glass half empty," driven by the belief there’s always more to do, though he acknowledges it's not always the healthiest attitude ([41:51-42:32]).

Quote:
"I've always said that to me, the light at the end of the tunnel... is the train coming to run me over. So I have to keep running, even though it's dark."
— Roy Wood Jr. [41:55]

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Notable Quotes & Memorable Moments (with Timestamps)

• "My life has just been a series of moments of just jumping into the fog without a parachute..." — Roy Wood Jr. [03:24]
• "You're asking me to stay around with all of these different variables? No...This is the best time to make myself available for some other opportunity. I'ma jump into the fog." — Roy Wood Jr. [14:25]
• "Political satire used to have the weapon of shame... We have a shameless society." — Roy Wood Jr. [16:31]
• "People think they're telling you that to make you feel good, but it's pissing you off because you're just getting more and more accounts of just how good he was to other people. But he fell short with you." — Roy Wood Jr. [21:01]
• "The boo was way longer and way worse..." — Roy Wood Jr. (on bombing at the Apollo) [36:26]
• "I've always said that to me, the light at the end of the tunnel... is the train coming to run me over. So I have to keep running, even though it's dark." — Roy Wood Jr. [41:55]

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Suggested Timestamps Guide

• [03:24] — Roy on the "moments in the valley"
• [06:49] — Fired over Twitter, leading to The Daily Show
• [09:23] — Early failed Daily Show audition
• [14:25] — On leaving The Daily Show and embracing uncertainty
• [16:31] — Satire, shame, and the current media landscape
• [18:41] — Growing up, fatherhood, and family revelations
• [26:31] — Breaking generational cycles & lessons for his son
• [29:04] — The hidden blessing of adversity
• [32:17] — Bombing at The Apollo Theater
• [36:26] — On facing and learning from failure
• [38:40] — Wrestling with perfection in parenting
• [40:20] — Legacy and giving back
• [41:51] — Roy on his "glass half empty" perspective

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Tone, Style, and Takeaway

The conversation is warm, genuine, and laced with humor, but unflinching about pain, fear, and family complexity. Both host and guest bring candor and wit, making the weighty topics accessible and relatable. For listeners (and especially anyone in creative professions or wrestling with family scars), Roy’s journey offers encouragement: that our greatest breakthroughs are so often born from our lowest lows—and the courage to leap into the fog.

Recommended for:

• Fans of stand-up, The Daily Show, and memoirs about resilience
• Anyone seeking perspective on family, failure, and personal growth

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Book Mentioned:
The Man of Many Fathers: A Love Letter to Non Traditional Fatherhood and Mentorship by Roy Wood Jr.

Transcript

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[Craig Melvin]

Hello there everyone. Craig Melvin here from my basement bar, my bourbon bar here. And this is Glass Half Full. This is where we talk about the moments and the milestones that shape or shape people personally, professionally shape people that you, you think you know. Roy Wood Jr. You thought you knew him at least. I thought I did. He's of course the hilarious guy who's a correspondent on the Daily Show. Bunch of standup specials acting as well the correspondence dinner where he brought the house down. He's also written a new memoir, more on that in just a moment. But Roy and I had a wide ranging and fascinating conversation. Deeply personal as well. He talked about his family. He talked about those, those little moments along the way that really turn you into who you are ultimately going to become. And there were some times where it got a little, little emotional as well. But I hope you enjoy our conversation.

[Roy Wood Jr.]

All right.

[Craig Melvin]

Roy Wood Jr. We, we like to start every athlete episode with a toast. I'm a bourbon guy, so I've got my, my nectar of the gods here too.

[Roy Wood Jr.]

I told I'm going scotch today. We're going scotch today. Craig Melvin. We going to pull up a little, little sip of that right there.

[Craig Melvin]

That's about four fingers. You my kind of, my kind of po.

[Roy Wood Jr.]

It's okay. I work on Saturdays. You don't want to work on weekdays.

[Craig Melvin]

What's one thing that Roy Wood Jr. Would like to toast?

[Roy Wood Jr.]

I would like to toast to free speech and may it long live truly and holy eventually.

[Craig Melvin]

Cheers to that, brother.

[Roy Wood Jr.]

Yeah man,

[Craig Melvin]

that's a good toast. I can get behind that. On the podcast we like to talk about Moments, the moments that have shaped who we become personally and professionally. The moments where you face your fears, just the big moments in your life where. What would you say is one of those defining moments that shaped your life?

[Roy Wood Jr.]

You know, when I look back at my life and I look back at the totality of it, most of the major things that really changed me were in my lows. It wasn't my highs. Like, it was never. Oh, when I did Letterman or when I booked that gig, everything changed. It was like, nah. When you found out you got fired from the radio station over Twitter, that was pretty monumental. When you made the decision to leave the Daily show, that was pretty monumental. When you quit on a comedy club Booker, who was 60% of your work at the time, that was pretty monumental. And all, like, very scary decisions, but necessary decisions. And for me, my life has just been a series of moments of just jumping into the fog without a parachute. And then, you know, I don't want to say figuring it out on the way down. You have some degree of strategy, but, you know, the moments where growth came in my career, they were not moments where everything was being wonderful and celebrated and beautiful. They were. There were moments where I was most scared, but also most courageous.

[Craig Melvin]

You've done most of your growth in the Valley, not at the top of the mountain.

[Roy Wood Jr.]

Absolutely, absolutely.

[Craig Melvin]

Go back to being fired on Twitter from the radio station.

[Roy Wood Jr.]

You know how radio is, man. Morning radio is crazy. Morning radio. I don't think anybody gets to leave morning radio the way they want. At the time, I was doing mornings at a station in Birmingham, Alabama, and this is a station where I had started as an intern when I came out of journalism school, and everything was cool. And I got into a dispute with the station. At the time, it was an internal dispute, but. But in 2010, I was doing. I took a job back at the station to host the show. Big deal. Hey, Roy woods coming home. He coming back to the station. That made him. As soon as I get back to Birmingham, Craig, I book a sitcom. Oh. Oh. So I go, hey, for three months, can I do the show? From a hotel room in Burbank, they say, cool. We do the show, everything's great, sitcom gets renewed, and. And I go back to my bosses and I go, look, give me three more months in Burbank. And the way they looked at it is that that was three months that you weren't in the community. And if you can't be in the community, we don't think you need to host this show. So we're going to give you a choice. Go do the sitcom or do this show. And I told him I would think about it. And I think just saying I would think about it was, it's like a relationship. It's either me or them other women. Let me think about it, bro. I woke up the next morning to Twitter notifications. I thought I was dead. People talking about, man, we gonna miss Roy. I always love Roy. I'm like, is heaven a Ramada Inn in Burbank? And I looked online, and they had sent a. They'd sent a statement to local media saying that the show was canceled. And the running.

[Craig Melvin]

That's kind of beat up.

[Roy Wood Jr.]

And that's a place that I given 12 years of my life to. And I'm not. I mean, it's. It's. I mean, we're 15 years past it, so I, like, I got a different mindset on it now.

[Craig Melvin]

Yeah, that's the business world.

[Roy Wood Jr.]

It can turn. It can turn on you in a heartbeat, man.

[Craig Melvin]

It can turn on you in a moment. It can turn on you in a moment.

[Roy Wood Jr.]

But if that don't happen, I don't get the Daily Show.

[Craig Melvin]

There you go.

[Roy Wood Jr.]

And that's, I think.

[Craig Melvin]

And that's one of the things I have found talking to a lot of people, like, you're in these moments where it's like, oh, woe is me. I can't believe I got fired. I can't believe I didn't get picked up for another season. And then all of a sudden, some time passes and it's like, okay, that window closed, but this door just flung wide open.

[Roy Wood Jr.]

Yeah.

[Craig Melvin]

And we're not. And we're not having this conversation. Had you not gotten to the Daily show, like, that would still. That would be the biggest moment, it would seem to me, for you, professionally.

[Roy Wood Jr.]

No. Yeah.

[Craig Melvin]

Yeah.

[Roy Wood Jr.]

By far the perfect marriage of my comedy skill set and my journalism degree. You just have to be prepared and you have to be ready, you know? And, you know, getting the Daily Show, I think not. Not just getting the Daily show, but working with staff.

[Craig Melvin]

You didn't get it. You earned it.

[Roy Wood Jr.]

That's fair. That's fair. Yeah.

[Craig Melvin]

They weren't like, oh, let's go out. Give it a. No.

[Roy Wood Jr.]

You earned that. You know, I had auditioned before and didn't get it. I auditioned in, like, 07, maybe 07, 08. I didn't know that, dude. I do. I hope nobody know, because it was a terrible audition. But the tape. The tape is out there somewhere, floating. They got the tape.

[Craig Melvin]

Was it one of those auditions where even in the room. You knew this, this. This.

[Roy Wood Jr.]

Oh, no. Is not going to take the story. Let me tell you how when I knew I wasn't getting it. So. So I'm. I'm sitting there, I go in and audition. I think it's okay. I go back out the room, and I leave my car keys in the room, so I can't leave. So I have to sit outside the audition room and wait for the person in there auditioning to finish. And I'm listening through the door. And this brother's murdering. Just every joke is killing. He hitting the inflections, and I can hear it. And he walks out the room. Yeah. See y' all later. Yeah. And they all giggling in there. And then I walked my ass in there, and everybody got quiet, and I come out. Oh, I. I left my. Left my car keys. Just get my car keys. Thank you. Hope to hear from you soon. You ain't going to hear nothing from me soon. That brother's name was Wyatt Cenac, by the way. Oh, just a little. Just a little dude named Wyatt.

[Craig Melvin]

No big deal. Yeah, he was a good guy.

[Roy Wood Jr.]

Black correspondence to do the job. Yeah. But Daily show was a blessing, man. It really was. And not just getting the show, not just earning that, but working with a staff that understood what my comedic voice was and amplifying that. At no point did they try to make me something that I wasn't from a talent standpoint. They let me talk about a lot of super black issues and make them funny in a way that. That work for their audience, man. So I. Yeah, I'd say, by far, the. The biggest feather in my camp.

[Craig Melvin]

I don't watch it as much as I used to. Just not. You know, part of it's just because of this, my schedule and small kids, but it does seem like sometimes that the show itself has lost its way. And I'm not sure. I'm not sure. And I'm not trying to put you on the spot because I know you're. You're an alum.

[Roy Wood Jr.]

Is that. Is that a critique of the Daily show or political satire as a whole? That's fair. That's fair. Because I sometimes wonder if the idea of losing your way is measured in the efficacy of the messaging. And does it reach you and does it get to you and does it resonate, or does the show have a sharp view or an opinion? Because the goal when we was there, when I was there, and I imagine it's still the same, is what can we say that no one else has said about this thing? Yet. And how do we make it funny? I wonder sometimes that the assessment of not just Daily show, but political satire as a whole is rooted in an exhaustion. And also because everybody got a camera phone, now they sitting in the car with a seatbelt on, giving you their opinions, too. So it's hard to avoid all of these opinions. You know, I think because part of why I left. Because it's just. It dovestail into this point a little bit part of why I left the show was because they were still trying to figure out what the hosting dynamic was going to be. I left before Jon Stewart was in the conversation. Right. And so we know it's not House in Minhaj. We may guest hosts. We may get a temporary. We don't know. We're not sure. And I'm thinking, all right, the merger's about to have this Skydance Paramount merger started years ago. Years ago. And I thought the merger was going to happen then. And so I go, well, it's a presidential year. If there's ever a year for there to be a new political satire show of any kind, if I ever have any shot of hosting something, thing one, I know it's not going to be Daily show, so if I want to host something I probably shouldn't.

[Craig Melvin]

Why did you know it wasn't going to be the Daily Show?

[Roy Wood Jr.]

I didn't. It's. It's relationships. Everything is relationships, bro. You know, whether or not somebody's into you, you know that they may not hate you, right? But you know whether or not they're into you. And if the rumor was Hasan Minhaj at the time coming out of the writers strike, when it was, when it was, when you discover that, as it was said in the media, we heard it was gonna be Hassan, but it's not gonna be Hasan now, so. Well, what are we gonna do? We don't know. Well, if you knew for sure that it was Hassan and you hadn't denied that, well, then I know for sure it wasn't me, because I was around the exact same amount of time when you were considering Hassan. I'm not offended. But I also am smart enough to know that it might not be me this time. Yeah, because you clearly didn't have a number two in mind. You've decided to completely revamp the search again. You have the right to do that. And I also have a right to decide whether or not I want to stay while you figure that out. So if I am out, because let me just walk you through my doomsday scenarios in my head at the time, you know, Hasan's not the host. Because the dialogue I had with myself was, if I'm not the host, but it's a host that I like and it's a host that rocks with me, then I will stay through the presidential election and then figure out where I land in the world of media. Well, I know it's not Hassan anymore. Okay, well, then who's it going to be? I don't know. Could be Chelsea Handler. Might be Sarah Silverman. There were rumors, you know, man, what if it's Leslie Jones? If it's Les, I like Leslie. I'll stay. I don't know if Chelsea would have me. I don't really have a deep enough relationship with her. She may bring in her own correspondence. What if the merger hits and they do a cost cut and they cut the show from four days a week to one day a week? Well, if you have a show that's one day a week, you don't need these six correspondence. But if you got a show that's one day a week, you don't need these six. You only six correspondence for a one day a week show. You don't. And if it's a merger, you're cutting costs. So the first thing you're going to do is cut salary, which means you're going to cut talent. I'm one of the senior correspondents, so in my brain, I'm in the crosshairs of that cut. And when you couple that with coming off of a radio show where you got fired over Twitter. Yeah, bro, they shoot movies and then don't release them.

[Craig Melvin]

Yeah, yeah.

[Roy Wood Jr.]

What's promised really? What's. What's truly promised in this. So you're asking me to stay around with all of these different variables? No. There's an election coming up, and if anybody's trying to do anything new, they're going to need talent for it. This is the best time to make myself available for some other opportunity. I'm a jump into the fog.

[Craig Melvin]

Took advantage of the moment More with Roy Wood Jr. After the break.

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[Roy Wood Jr.]

Bringing it back to your point about feeling like the show has lost his bite, what I sometimes also feel like political satire used to have the weapon of shame because the person that the jokes were targeted at had shame. We have a shameless society. You can't embarrass people anymore. So if I can't embarrass you, then how much teeth? It limits the efficacy of the joke or the humor or the thing that you're, you know, that you're directing at somebody.

[Craig Melvin]

My grandma Florence used to ask that question all the time and she would, she would see something that was just inexplicable or run across something that was just crazy. She would always say, boy, whatever happened to shame?

[Roy Wood Jr.]

Whatever happened.

[Craig Melvin]

And back then, like when we were kids, we were like, yeah, people should. And now you're right. Like no one's embarrassed about anything. No. Speaking of family. Yes, Roy, you write a lot about your family in the book. First of all, it's not pg. We want to make sure that they're not elementary school kids. Elementary school kids can't read this.

[Roy Wood Jr.]

Somebody asked me, they were like, you should come to the library or the reading program.

[Craig Melvin]

I was like, no. If you do start with the story about getting picked up at the liquor store by the guy at the liquor store and he wanted to make sure that you knew he was a drunk and not a pedophile. Yes, it resonated with me because I'm pretty sure in my childhood there was a point where my dad pulled something like that too. But let's talk about dads. Because people who know you, they know the Don Cornelius story. They know how there might have been a universe in which you didn't have to work if your dad had actually stayed on. As the EP of Soul Train.

[Roy Wood Jr.]

Correct.

[Craig Melvin]

But there's stuff in the book that you write about your dad that I don't think a lot of folks know. There's this dad that the world sees, and then there's a dad that Roy Wood Jr. Sees. Growing up, was there a moment when you were a kid when you knew that your dad may not be or what he seemed to everyone else?

[Roy Wood Jr.]

I'd say when I. The first time I saw him and my mom argue, my parents were separated essentially by the time I was born. Married, but separated, you know, it just. It hit the fan for them real early. And then somewhere around third, fourth grade, my parents reconcile and we move in. We moved. My mom and I moved from Memphis to Birmingham, and we move in with my dad. And because I never had my father in my home up until third or fourth grade, I didn't really have a concept of what the role of a father was. It's just. I have a dad who comes to Memphis once a month. He checks some homework, he take me to Liberty Land, shout out to the old school Fair park in Memphis, and then he'd drive back to Birmingham. Because I have aunt and uncles that are in loving relationships, I understood my parents dynamic was a little different. Like, they didn't sleep in the same room. I'm the ninth. I'm my mama's only child, but I'm the ninth of 11 kids. I have two younger half brothers with whom my father was raising with another woman. So there were nights my dad didn't come home. But I'm used to him never being home. So if anything, the nights he was home were kind of the more odd nights. But it just felt like parenting. And also when we got to Birmingham, you know, my mom had a much more affluent kind of, you know, black, not aristocratic, but, like, she was around more successful black folks in Memphis. Got it when we got to Birmingham, and I got my Little League teammates and they got a mama that's an alcoholic. And then you ride home with these teammates and they got the abusive stepdaddy. And I saw every possible bad home. I just came home. My dad just wasn't home. That's like, Memphis. All right, cool. Like, it didn't seem like dysfunction, but it wasn't until middle school and high school when my parents started arguing a lot more, that it started dawning. On me, the history between them and what that means. Like, damn. Like the days where you dread seeing your pop's car in the driveway. And I don't know if anybody can relate to that, but there's. I can relate.

[Craig Melvin]

I can relate. Yeah.

[Roy Wood Jr.]

You walk in the house and you see his keys on the counter, and you just take a deep breath before you walk through that doorway. Here we go.

[Craig Melvin]

Here we go, right? Here we go. Let me brace for some drama, you know?

[Roy Wood Jr.]

You know you have a man that has won every journalism award, interviewed every relevant person. My pops covered every major war and riot, from the Soweto riots and Zimbabwe up to Rodney King. You name a riot or war, he was there. I know, but at home, there's. There's. There's a. There's a lot left to be desired. And it wasn't until my pops died when I was 16. And you get older. And when I got the job at the radio station, the radio station, everybody at that radio station was essentially hired to some degree by my dad. They all got their ends in journalism. Everybody in journalism in that city knew and worked with my pops. And the older I got, the more you start hearing all these great stories about this man. And people think they're telling you that to make you feel good, but it's pissing you off because you're just getting more and more accounts of just how good he was to other people. But he fell short with you. One of the worst things that happens. I followed my two younger brothers on social media, and I love them to death. And we tight. I'm tighter with them than I am any of my older siblings because of the age gap differentials. But my two younger siblings, they. When Facebook first started, whatever this nonsense is, six, seven years ago, like, you know, Facebook could just show you a picture and remember the memory from the good old days. Right?

[Craig Melvin]

Right.

[Roy Wood Jr.]

I don't, bro. I don't even go on Facebook or Instagram on Father's Day or my pop's birthday or the day he died. I don't touch social media because I know they're posting tributes to Pops. And it's not that I don't love and don't appreciate what good things I was able to glean from my father, but my little brothers will post a picture, and they got the old school Polaroid joints that print it, and it has the date at the bottom of the picture. So they'll post a picture with them and dad doing some regular him at football practice watch. He never showed to none of My stuff, he never go to Nana Masto. Pictures of them on road trips. And Craig, I can look at the date on the picture and tell you whether or not the lights was on at the house, that me and my mama was staying there. And so I don't know what you do with that. I don't know how you put that together. The one thing I'm thankful for is that I was able to do finding your roots. And that television show gave me a lot of insight into my pop's upbringing that he never gave me because he never brought me around. Most of the folks on his side, not extended family. I know all my siblings, but I don't know cousins, aunts, uncles, or I don't know nobody over on that side of the family. Met them all once at his funeral. So I go on that show and Henry Louis Gates starts talking to me about how my dad lost his dad when he was four. Then when he moved to Chicago with his mother, there was no. According to census data, there was no new male head of household ever in his life. When he was 16, he suffered a debilitating physical trauma. So now you're disabled for the rest of your life and you got no pops to pour self esteem into you. At some point, that depression is going to manifest itself in one of many ways. And for him, it was sex or women or whatever. Whatever attention. It was eroy.

[Craig Melvin]

It's funny you bring that up because for a long time I harbored this resentment toward my dad. Charlamagne and I have talked about this a fair amount. And I mean it to the point where, like, we were estranged in my teens and twenties for a while. And as I got older and as I started doing what I'm doing now, you know, journalism and talking to folks, meeting different folks, asking questions, questions. And my aperture was widened. And you get to a point where you realize, well, my dad was an addict. And I didn't fully appreciate how that addiction would manifest itself in fatherhood. And then I got to a point where I started doing some research. My dad was born in a prison in West Virginia. My grandma, she ran numbers, she ran liquor. She got in trouble, she got locked up. And I tell people one of my sources of pride is she was in the same prison as Billie Holiday. But so he grew up never feeling like he belonged. His father was never around. And when he did come around, he didn't even know who his dad was until he was 12 or 13. My father. And so for a long time, I was expecting him to be something he wasn't capable of being. He hadn't seen it.

[Roy Wood Jr.]

So he couldn't get the training. Never got the training, never got the trainer.

[Craig Melvin]

It's that generational trauma we all always talk about. But. But you. You're breaking it. You have a son. Yeah. And how old is he?

[Roy Wood Jr.]

He's nine now. And I have been around, you know, when I was holding him when he was born, you have the thoughts of all the things you're going to do with your son. You're going to do this, do this. And, well, who did I learn that from? And. But where did I learn that? And I'm sitting there holding my son, and I just realized so many moments that my pops, my father and I never had, and it made me really angry. And then as I started thinking of all of the people that somehow I guess filled in the gaps, whether they know it or not, on being a mentor or giving me game, I became very touched and proud. And I was like, well, because I don't want to die early, Craig. And my son's account of me is good stories from strangers. So let me tell you who I am. Let me tell you why I am the way I am. And some of that is your granddad. But a lot of it is people that. I'm just grateful that God put me in their orbit. And that's the book. It's just stories of the end. Some of it's funny. But at the end of. At the end of it all, there was something to be learned, there was something to be gained. And I speak as much as I can about the complexities between my pops because it's not an indictment of him. It's just all in the spirit of how these things changed how I grew up. If you argue with my mom and you don't pay the power bill and you know, she's in law school and all of her money is tied up in tuition and what little bills she can pay. That's manipulative. It's abusive at its core. So then I see that, and then I go out and I start working 30 to 35 hours a week at 15 and 16, so that not knowing the next time you and your mama, you and my mama get into an argument and you don't pay something, I can go upstairs to the Nike shoebox and pull out a hundred dollars and give it to my mom, and we can make sure the heat stay on so we ain't sleeping triple layered. So that in turn gave me the work ethic that's made me everything I am today.

[Craig Melvin]

See? See, it's.

[Roy Wood Jr.]

What do you do with that? Well, people go, Roy, you work hard. Yeah, but I worked hard because.

[Craig Melvin]

But that's. That's the blessing. That's the blessing. Have you ever thought about that? Because I've thought about this sometimes. Like, if I had grown up in a house with Heathcliff Huxtable, not Bill Cosby, Dr. Huxtable. If I had grown up like that. I don't know if I'm talking to you like this. If the road had been smooth for 18 years, would Roy Wood Jr have been as funny as he is?

[Roy Wood Jr.]

No.

[Craig Melvin]

As insightful as he is? No. I don't think so either, do you?

[Roy Wood Jr.]

That tenacity was birthed from a need to survive. And I'm not gonna sit here and act like I had the craziest, most, toughest, most poverty Ghost Face Killer. Pick the roaches out the cereal.

[Craig Melvin]

John.

[Roy Wood Jr.]

John peed the bed five in the. We had. We had dessert some nights. Not only did we have meals, we had dessert. But also, there's an emotional trauma that comes with that. And it to the point of that, like, changing the way you move. And I had. I remember my junior year of high school, we get to high school early, and we walk the halls and socialize. You just don't go to class. You don't go to homeroom, right? And our principal pulled me aside and pulled me into his office one morning, and he showed me the list of everybody in the school. He showed me everybody's GPA. And I had the second to last GPA in my class at a 2. 2. The person below me had been expelled. And the principal's giving me this long lecture about the education and the importance. And you must. And I just. I couldn't tell them because it was illegal. I thought my mom or somebody would go to jail. But I'm like, bro, I work 35 hours a week, and then I come to this building and try to learn this. So sorry If I forgot Ms. Shaw's US history homework. There's a joke I used to tell back in the day when I was younger that I was a C stud and I didn't want A's, how much do I need to know to not take this class again? That's a C. But that was my approach. And once I learned that standardized testing can offset lower GPAs, and my mom is an educator. My mom's been in higher ed for coming up on 40 years, 50 years now. We had all the Kaplan act and SAT practice test. Man, I act out the roof and got in college. I think I graduated school ultimately, like maybe a 2, 5. But you can't explain to someone, hey, my grades are low because I'm breaking child labor laws to make sure there's enough money to make sure the IRS doesn't take the house because my father didn't believe in paying in taxes. And when he died my senior year, the first thing the IRS did was try to come for the house and the cars. So I had to take a day off from school to take all of his collectible cameras and sell them at pawn shops. So, yeah, I missed the history test.

[Craig Melvin]

Yeah.

[Roy Wood Jr.]

Sorry. But the hustle, the ingenuity, you call the audibles, and when you get out on the road, you know how to survive anything. Hang on. I'm take a sip after that one. Because I'm going to take a sip.

[Craig Melvin]

You take two. Take two. We're going to pivot to a section called Craig's Curiosities. These are just things that I've come up with that I've always been curious about.

[Roy Wood Jr.]

All right, Chris. Curiosity. Curiosities. Go.

[Craig Melvin]

Tell me about a time that Roy Wood Jr. Bombed on stage.

[Roy Wood Jr.]

The Apollo Theater probably stands out as the most legendary.

[Craig Melvin]

Not the Apollo.

[Roy Wood Jr.]

Yeah, the Apollo. Not just like a regular. You know, like, Apollo is like a functioning.

[Craig Melvin]

Yeah.

[Roy Wood Jr.]

Talent place outside of the TV shows we see. I went on and basically I. I was nervous. They smelled it. I was talking too fast. I didn't have confidence in my body language. And technically, I didn't get booed, but I got booed. So you're supposed to perform for three minutes. Somewhere around 2 minutes, 20 seconds, I can feel the boo. This is what they don't tell you about the Apollo. The Apollo is. It's a very wide room, but it's shallow.

[Craig Melvin]

Yes.

[Roy Wood Jr.]

So everybody's right up on you. Like the Apollo Theater, from stage to the back of the room is like sitting across a high school basketball court. The same way you can see somebody's face on the other side of the court. That's the back of the Apollo. So you can see every single black person's face. And you can see the disapproval just slowly dripping down they face. You can see muscles starting to contract as they prepare the boot. You can see the collarbone. You know, you get them little ligaments above the collarbone. Get the stretching. And I could feel the boo coming. And I cut my performance short, and I said good night, and I walked off the stage. And as soon as I walk off the stage, it's time to go back out on the stage to get Kiki Shepherd. Because it's me and the other comedian, we were separate. And in those days, this is 2002. In those days, amateur comedy was separate from amateur night, so it could be judged more fairly. Yes. So they bring me and the other comedian back out on stage and we stand there. And now Kiki shepherd is standing over. They needed to get her first gun. Give it up. What y' all think about Dexter? Angry. Yeah. And now what y' all think about Roy Wood Jr. The boos were longer and louder than what they would have been had you stayed on stage. Stayed on stage. If you'd have just stayed on stage, at least the sandman could come get you. And then you can do something funny with the Sandman and just go, oh, I lost. It's okay.

[Craig Melvin]

More with Rory Ward Jr. When we come back.

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[Craig Melvin]

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[Roy Wood Jr.]

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[Craig Melvin]

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[Roy Wood Jr.]

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[Roy Wood Jr.]

Prices subject to change.

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Visit today.comxfinity for full offer terms and details. Hi, it's Kate Snow, NBC News anchor, host of the podcast the Drink. This month, I'm grabbing a matcha latte with comedian Taylor Tomlin. The Drink is always about someone's journey to the top, and Taylor's story is remarkable. She tells us all about her unlikely path from performing in churches all the way to headlining her own Netflix specials like her latest Prodigal Daughter. And she opens up about her religious upbringing, what drew her to stand up and how she feels when she gets on that stage. Hope you'll listen and follow the Drink wherever you get your podcast,

[Roy Wood Jr.]

but it's that Thing of that, you can't run from failure, bro. You can't run from the boo. Learn from it. Base yourself in it, man. The boo was way longer and way worse. And the Apollo Theater, also, here's another important little fact about the TV magic y' all don't know. After you get booed and the show ends, you just leave the theater, and now you're out on the sidewalk with the same 3,000 people who booed your ass 20 minutes ago.

[Craig Melvin]

And they're this close to you.

[Roy Wood Jr.]

Yeah. And they all put their head down and like some New York. And this is New York. This is my first time in New York as well. So it's just a whole week of just culture shock. You gotta tighten up, man. You gotta tighten up. It's all right. It's all right. You have some guts. You came up here, you came up to New York. You got some guts. All right. All right. But you gotta tighten up. That was a rough one because that was also my first television credit, and I'm out of college, and, you know, it's happening. My career. Good. I'm finna be in the Ice Cube movie. Wrong.

[Craig Melvin]

Wrong. But again, had it not been for that moment, you don't end up where you are now. Yeah, the booze shaped you.

[Roy Wood Jr.]

It got me in a place where that following year, like BET's comic view was the premier comedy showcase show. And an appearance on that show would ensure that you got booked at numerous clubs and your money got. And your money went up by being booed on the Apollo. I no longer have tape to submit to bet. So that essentially regressed me to for about two years before I could finally get a comedy club tape that was decent enough that BET people could forget about the boo.

[Craig Melvin]

Two quick questions for the road. Give me one moment. That Roy Wood Jr. Is still chasing perfection in parenting.

[Roy Wood Jr.]

Man.

[Craig Melvin]

We're all chasing that. Is that realistic? That's not achievable.

[Roy Wood Jr.]

I don't know, man. It's the idea that I'm not present enough. I know I'm not present enough. I'm gone for a reason. I make sure my son knows why. But the idea of I can lay down and go, all right, I did a good job today because I feel like you have work, you have parenting, and you have rest and recreation. I feel like you can only pick two of those a day to be good at.

[Craig Melvin]

That's fair. I just. I don't know. I would maintain that. Someone said to me years ago, because I, it's better now because I've got a more of a set schedule. But when I was crisscrossing the country as a correspondent, yeah, I'd spend three days somewhere and wouldn't see my son or later my daughter. But quality over quantity. So if I, you know, you make sort of make peace with the fact that you're not going to be at every baseball game or basketball game or recital, but when you are around, you're there and you're dialed in or. And I tell my kids all the time, I'm like, you know, I'm gonna miss some stuff, but we're taking hella vacations. Which is, which is how I make up for the guilt, you know.

[Roy Wood Jr.]

Yeah, I try to do that with my son, man. I try my best. The thing I try to communicate more than anything in detail is why I am away and what is happening when I'm away. So we swap videos. Hey man, I'm in Vancouver today. This is, this, this is a sound man. Here's the job that is occurring today so that you don't just think I'm away and that you're not being thought of.

[Craig Melvin]

What's one moment that you would hope people remember you for?

[Roy Wood Jr.]

I just hope that Florida A and M and the city of Birmingham know that I always rode for them and always tried to do stuff to help them. I know that at the end of all of this, in terms of my entertainment trajectory, all roads lead back to Birmingham. I'm lucky, bro. I'm very lucky to be. To make it out of a place where a lot of folks don't make it out of. I'm talking about Alabama. And so to be able to go home and do what I can to pour back into local programs. Yeah, you know, I do what I can now on the literacy and the reading side and there's, you know, there's literary nonprofits I work with and Birmingham Urban League and my high school. We try to do stuff to promote sports and, you know, trying to be part of people that, you know. Major League Baseball came a couple years ago for the Willie Mays trip.

[Craig Melvin]

I was there.

[Roy Wood Jr.]

And then they poured money into the west side in Fairfield and redid his park, which now creates a viable facility for local kids to now play the sport of baseball without having to travel with impossible public transit to another side of town to do something that'll keep you out of a gang and off the streets. You know, I'm just somebody. I love my state, I love my college, I love my son. And I hope that my body of work will show that all three of those things were the truth.

[Craig Melvin]

You know, the show is called Glass Half Full. Would you say you consider yourself a glass half full person or glass half empty person?

[Roy Wood Jr.]

Half empty.

[Craig Melvin]

That was quick. That was quick.

[Roy Wood Jr.]

I don't think I've ever stopped and rested my laurels on anything that I've done or accomplished or a bright side. There's always more to do. And I know that that may not always be the healthiest approach for the proponents of mental health and self care, but when you have opportunities, you have to seize them. You know, people talk about the light at the end of the tunnel. I've always attend. I've always said that to me, the light is the train coming to run me over. So I have to keep running. Even though it's dark. I don't know where I'm going, but I know I have to keep going.

[Craig Melvin]

Cheers, my friend. The book is a. It's a great read.

[Roy Wood Jr.]

I appreciate you, brother.

[Craig Melvin]

It's a love letter to fatherhood and not traditional fatherhood.

[Roy Wood Jr.]

Yeah.

[Craig Melvin]

Cheers to you worldwide.

[Roy Wood Jr.]

Thank you, brother. Good times.

[Craig Melvin]

Well, there you have it. Roy Wood Jr. And you thought you knew him, right? His book, by the way, it's called the man of Many Fathers. A Love Letter to Non Traditional Fatherhood and Mentorship. I would maintain, but I really enjoyed that. I hope you enjoyed it as well. Hope you enjoyed the podcast. Thank you so much for joining me on today's edition of Glass House Half Full. If you enjoyed our conversation, the corporate overlords want me to encourage you to like, subscribe and share this episode with your friends. Even if they're not your friends, you could share with them, I guess. You can also drop a comment and let us know what you thought of the conversation. I'm even open to suggestions for future conversations, areas for improvement as well. Leave me a comment. I'll see you next time. Cheers. The Glass is Half Full this episode of Glass Half Full is produced by Sadie Bass, Tyree Nobles and Jarrett Crawford, along with Lilia Wood. Our editor is Ali Strom and sound design and mix by Joe Plore. Additional production support provided by Ann La Gamayo, Bailey Coronis and Megan Sarnacki. Ashley Domagola is our production manager. Our head of audio production is Jessica Finton.

[Roy Wood Jr.]

Ariana Davis.

[Craig Melvin]

Santana is our executive editor. I'm Craig Melvin and this has been Glass Half Full, a production of the Today Show. See you next week.

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