How Getting Arrested Saved My Comedy Career | Roy Wood Jr.

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This is me and I can kick new a stand-up comedy. He goes, "Yes, so long as it's not in the billets." There were days where the gig put cancel on you while you were driving there, and that gig was the gas money home. You sleep in your car that night, and you get a construction job for eight hours. You get the money? You drive your back to Birmingham. You have to show the game what you're willing to give up. Do you think if you never got arrested that you would have gone into comedy? If I'd never get arrested, I'd end up in prison for something worse. Were you feeling killed? You know, just knowing that your dad wasn't there as much, and you were away from your son, like, what was that feeling like as a father? So, you wrote a book that talks about you being raised by many different fathers. So the man and many fathers is essentially, so here's what happened. When you have a child, you start trying to figure out how you're going to teach the child the things you want to teach them. Before you can figure out what you, and how you're going to teach them, you have to think back of, well, how was I taught those things? And then you start doing a bit of a parental audit on your parents and what each parent did or didn't do and what they were present for or not present for, and my father passed when I was 16 years old. So I didn't get everything, I didn't get, I didn't get the game from him. Not everything I could have been shit of gotten because I was too young to know what questions to ask, and he was too old and tired to tell me. So for whatever reason, I didn't get everything that I needed from that man. When I look back at my life as a whole and everything that I have of worth and just what values I hold, I learned them from other people, other men. And it's not a knock on the women in my life and the women that I've come across and been blessed enough to interact with who have taken me under their wing, but as a young teenage boy with no father, the first thing you seek out is male guidance and leadership. My mother was still on this earth. So if I needed advice from a woman or I needed a more delicate touch on something, I had someone to go to for that, I didn't have anybody to go to for the mentorship side of the game. So that became a almost like a, not inert, but unconsciously I would gravitate towards man never older than me because I just, I needed guidance, I needed something. And the more I looked at the lessons that I wanted to teach my son, I started making a list of all of these, these men, these people, and the more I looked at the list and the lessons I learned from them, I was like, oh, this probably could be a book because this is all a bunch of short stories. Yeah. So I mean, you have like grand mentors, like of course there's professors and former bosses, but then there's also pamps that I learned stuff from this gang members I learned stuff from. It does not matter. I think that if we really all look back at our lives and had a moment of reflection of where you learned certain things, I bet you half of it didn't come from under your home. And so with that, armed with that knowledge, I set out to make a book and I called it the man and many fathers, you know, it's really more than anything. It serves as kind of a preliminary life rule book for my son to have some guidance on. Should I pass before I can give them all of the game? And so given you writing this book about having many different father figures, mentors in your life, growing up in Birmingham, Alabama, did you not have the best relationship with your father or did you not get the guidance at home? I mean, a little bit. I mean, but you have to remember who, like my father, you know, my pops was a different type of dude. You know, my pops is a civil rights area journalist. So he was a radio news reporter and, you know, he dedicated his entire career to telling stories of black struggle. So he wasn't always home, you know, so there's that. I'm my mother's only kid, but I'm also the ninth of 11, you know. So you don't have a man that's always home and present and a fatherly sense. But you knew who he was as a professional. I mean, Hill, when I look at what I've done and my body have worked the last 10 to 15 years professionally, I'm just a funnier version of my dad. Oh, what's the black issue? Cool. Let me sprinkle a joke on it. All right. Let's talk about it. My dad just did it with vitriol instead of humor. Do you feel like you ended up getting into this profession because even though you didn't have the best relationship with your father, you still wanted to be like him in some kind of way? I don't want to be like my dad. But I grew up, I grew up somewhat resentful because yeah, you got another family across town. And I know how that makes my mom feel so I can't be completely cool with you about that. Yeah, you, my pops, all right, go grocery shopping, we talk about dating and getting your learners premium, all right, but there was always this angering resentment underneath all of that. And so for me, as I got older, you know, I got into my 30s, my comedy became more socially aware, more socially conscious. I just had to sit back and realize I'm him professionally speaking at least of him. I'm the same, we're the same, I am an extension of him and they're still honoring that because we both worked in service, you know, of America, but first and foremost, black Americans. Those were the stories that he fought to tell, to bring light to those were the issues that he fought to have conversations with lawmakers about, I'll try to do jokes about the same things, you know, and, you know, you can have all of this anger in your heart as somebody, but it's not going to get you nowhere, it's not going to do nothing for you. You know, I got into journalism because I want it to be true, it's got that's why I got into journalism. I didn't get into journalism because my father had a 50 year career in it. I thought that was so cool and so fascinating. And then you just look up and it's just, yeah, I'm him and there's nothing you can do about it. And so, you know, one thing that was really cool, I did the White House correspondence dinner. So my pops is a co-founder of something called the National Black Network, which at the time in the 70s was a syndicated radio service that delivered news focused on black American issues that did not exist prior to that. So if you were a black person and you wanted to know specific stories that were happening that are relevant to what you believe in, you'd hope the regular radio news broadcast would carry it, but my pops and some other gentlemen in Chicago at WVON, they create this syndicated service where they're recording three, four minute news packages and then sending them things out across the country to black radio stations. So you knew the news without having to leave black music, so it was, it was very similar and creating the sense of black journalistic media, which eventually extended to the growth of television and BET news and, you know, everything that TV one was doing, radio one at the time. So I get on stage at the correspondence dinner. I start talking about the attacks on the media and the censoring of the media and the media, the cuts and their firing local reporters and like radio news reporter doesn't even really exist as an occupation anymore unless you're at NPR and I don't even, as of today, I don't know if they have funding right now. So the correspondence dinner is the section in the room and there's a table in the center of the room and it's pretty much all black journalists and so many people at that table at some point in their life worked with my father or were hired by him at some point in their career and these people are serious ferocious fighters about issues to see that part of his legacy was humbling because I'll never have that. Yeah, you told this story that really inspired me that says there was a point where your dad was he was sick and he wasn't doing to well and he asked you for a baked potato. And you go and get this baked potato and he takes a couple bites and he says, how did I do? And you were thinking that he was talking about this baked potato. But later you realize that he may have been talking about just as a father, how did he do? And knowing what you know now and having these experiences, does that change the way that you view your father? I don't, in hindsight, I don't think it was a fair question to ask a 16-year-old because you'd never given me all of the information I needed to make a fair assessment of that because I need to know why you did or didn't do certain things, you know. I think one of the biggest things that I learned over time with my dad was the most beneficial piece of information I got came from Dr. Henry Lewis Gates when I did finding your roots. And so, you know, I go on the show, you know, the DNA show where they tell you you're lineage and they track you back as far as they can through paperwork and all that. Dr. Gates discovered that my dad lost his dad when he was four. He was disappeared in the middle of the night in Southern Georgia in the 1920s. So, you already know what that means. That's straight up lynching. Like, nobody just doesn't come home. That doesn't happen in a set, not in those days. So, so, my pop-source is pop-source when he was four. Then, through census data, they find out that there was no male head of household. There was no man living in that house with my dad and his mom. The rest of the time that he was, you know, a child. He was 16. He had a terrible accident and was disabled for the rest of his life. He went with a lamp and a cane. At 16, he had a cane for the rest of his life. He can't imagine what that does to yourself a steam. You got to work in mom, but you ain't got no man that'll help build you up and get you that confidence back. I would imagine those two things shaped the entirety of his arc. So, when you have that information now as an adult, it's hard to be as mad as you was. It's hard to be as you got to let a lot of that go. And that was the main thing I learned in writing this book was that so much of what I felt towards my pops when my son was born because, oh, I didn't, he wouldn't have for nothing. I've been here for all of this stuff. And I don't have no pictures of him when I was two. What was he at? Like that type of stuff. You let go all of that when you be like, oh, yeah, he had his issues too. We forget that our parents, our parents got a lot of unpacked stuff too. Right. And we assume them to be perfect because we're always the grandness of our parents. They're these larger than my figures. And then you get grown and then you go, well, you didn't do everything. Well, no, I didn't. I didn't know what I was doing. You know, I'm self-medicating with women. So, I'm having babies all over the place. So, it's the question of how did he do the eyeness of the answer that doesn't change. Yeah. But the reason that it was just eye. Right. It's a little bit more understandable. And it's sad and it's unfortunate, but it's an essential journey to go on. I encourage anyone to really sit and evaluate why your parents weren't what you needed them to be. And they may not give you the answer because a lot of parents are too old and too callous to their own ways because they don't want to confront. Right. Like anybody that's ever done working themselves, they know you got to take accountability for what your demons are. And you got to own your demons. And then you have to figure out how to fix them. So, if you're going to your parent and going, why weren't you this, this, this, and this, they're going to have to sit and have some long thoughts with themselves. And for a lot of them, you don't know what the trauma is. They may not ever want to unpack that. Right. Because they know it will devastate them. So, you're not going to get what you need from your parents, but you have to try and identify and triage it as best you can so that you can understand when those impulses might be appearing in yourself and how to not pass that down. If your son, one day, was to write a book about his father, you, what would you hope that he would say? I hope he would understand why I was away. I hope that he would understand that the moments I missed, I missed because I was trying to support him. It's not up to me what he says. All I can do is be clear about what I was trying to do and what my intentions were. And I think that's more than what I was extended from my dad. So, I think if you give your kids at least that, you know, he's not going to have a big potato conversation with me to write about. So, you lose your father at 16 and then you end up getting into college and then you have this experience in college where you end up getting suspended from college and you get arrested. Yeah. Can you walk me through that all the way around? Okay. So, you got arrested and then you get suspended because I got arrested. Got you. Where'd you go to call you a Florida in them. So, you kind of have to rewind it. So, my pops income was the bulk of the income in the house. No, my mom worked, but there were two, there were two income household. My dad dies. That's half the income. So, that's an issue. And, you know, my dad was so pro-black. He didn't pay taxes, right? So, with a lot of black men. He didn't pay taxes. My father didn't pay taxes because the Voting Rights Act had an expiration date. It was only for like 50 years or whatever. And his feeling was that and that's still not full citizenship. So, if I'm not a full citizen, I'm not paying taxes. So, he just didn't pay taxes. And the government just let him walk around for years. He just didn't pay taxes. And then when he died, oh, Lord, the IRS came to try and take the house. And so, the house you were living in. Yeah, the house we're living in. And so, this is my senior year of high school. Imagine setting your makeup then forgetting it's even theirs. Meet new, grippy setting mist from Maybelline, New York. Gel to mist technology locks in your look for up to 24 hours with flexible all-day comfy grip. Try new, grippy setting mist from Maybelline, New York. Maybe it's Maybelline. So, you're dealing with the passing of your father and the IRS trying to take your house. He's mad and the funeral hasn't happened yet. And the IRS is like, yeah, I'm going to need you to have me by the end of the month. And we like, how much? And just like six digits. And my mom is still legally his wife. So, she's the, she runs the estate. Did you guys have any idea that this issue was happening? Or we didn't, we didn't, you don't think that far down the road. Right. You're just like, oh, you don't pay your taxes. That's crazy man. Anyway, what we eating. Yeah, yeah. And then when the IRS shows up and goes, yeah, we need this house because he didn't pay taxes. The house is in his name. So my mom sent me down. My mom's a G man. Like, so she basically comes to me as I look, we have a fair out of way to pay these bills. I was already working part time or whatever. So I'm kind of like, all right, what's the number? What do we need to hit every month? The objective became my senior year to make it so my mother did not have to worry about me. It's clear to me. You got all this other stuff that you're dealing with. So you deal with that. I'm going to work another job or two. And my senior year after my pop star, I was working 30 hours a week. My senior year, my grades dropped. Of course, you know, in baseball season was a little tougher because we had practice and games during the week. So I was working 12 hours, 14 hours on the weekend, still getting a 30 because we can't pay the bills. Stuff's got to get paid. I got to fix my car broke down. I got to fix it. I can't go to my mom with that. And I got to have a car because she can't pick me up because she had a second job. So the idea of hustling and not being of concern to her became very important because we were just fighting to keep the basically the playbook she ran was I'm going to stall out the IRS and the courts until you leave for freshman orientation in the summer. And then my mom had a lot of grief so she knew how to I'm going to extension, continuance, extension, continuance, ask for new discovery. Just just drag it out till next summer. The daily for freshman orientation. I'm going to give them the keys to the house. And I'll go get an apartment and I'll restart and I'll build my money up and I'll get a house in which she did later on. But that was the playbook when my dad died, he was just keeping the lights and the heat on. So I did my part. The only reason I got into college is because I had outstanding standardized test scores. Everybody looks at C students and they think that you weren't smart was a lot of C students. They were just busy. I'm sorry. I didn't do the essay correctly. I was doing construction at one in the morning on the Interstate. My bad with that behavioral hardware pre-installed from high school. I'm in college now, we're not in college, it's still ain't got no daddy. Still got a mom and she's making stuff work, but I've watched her struggle for so long. I can't call you about this car repair or I want some jeans like you need a whole new wardrobe in college and you want to have a little money to go to the club. You want to underage drink. You want to take a girl on a date and a money. So you start figuring out ways, you got to work, study, and the post office has a mail sort of. I'll take a credit card. I use this credit card to buy all of the stuff that my mom would always figure out a way to get from me, but ain't no telling what level of stress she had to go through. To get it, I'm going to take that off your shoulders and so there's a desire to be independent before you have the know-how and the way, you know, so much of what I've done and trying to do in my life is to make my mother's existence more soft because she deserved it. And then I got arrested and now you got to put up money for a little bit of my bad joy. All that money you saved, yeah, go ahead and put that into a nice attorney for your son so we don't get sent off to a prison. Are you comfortable saying what you got arrested for? Yeah, it was a mail theft. That was, I mean, credit card fraud was the main offense, but because I worked in the post office, all you stole this card from the post office. So we're going to drop all the other charges and we're going to charge you with mail theft, which is a federal charge. And then you face five years of prison, which I ended up getting three years of probation for, which I didn't know at the time I was going to get probation. So like, I get a court appointed attorney and so this is how I got in the comedy. This arrest is the catalyst for why I'm even sitting with you today. So you were not in comedy prior to the year. I was right. I was funny. I had crack jokes and yeah, in her mirror, flat football, I was like, okay, I wrote the bench and baseball on high school. I was a funny person. You're all like kids growing up would always tell you that you're like the class clown kind of a thing. I wasn't quite class clown. Like the quiet one who was tonight, who you didn't think was funny, wait a minute, who said, you funny? Like I was that guy. I didn't want to be the center of attention. Like I would tag the class clowns like that was my job. So your job. So you get arrested and like the police came to the house. This is the night before Thanksgiving, 98. They come to the house, the door, and what do you know, I really thought you're living with your mom said, no, this is, I'm in Tallahassee at this point. I'm in a don't. I'm off campus in an apartment or whatever. This is my junior year of school. And did you know that they were after you? No. We're at the house. We just bought the clothes and chillin in the, because the way we got caught is. The woman that rung us up, we knew. And so as a favor, because she knew the card was stolen, she undercharged us to leave more space on the card. So we could buy more stuff later, which I didn't understand because I'm like, I'm never coming in here again with this car. But she, she undercharged us and that flag store security of dealers. So, because it's like Tommy Hill figure like super, let's just say she worked in the Tommy section or might have been polo chaps back then, but let's just say every sweater in this department costs $90. She's ringin' stuff up for $4.53, like just ridiculous discounts. And so they caught her and then eventually, you know, lean on her and have and she told her that I know where they live, here's their address. They came to the house from, and with the wilders that I just ordered a pizza and I heard that knock at the door and I thought it was the pizza, it was not the pizza, it was the police. They come in for everybody on the ground, we go to jail, I end up standing jail over the weekend because it's Thanksgiving, week or whatever and, you know, there's snow, hail hearings or whatever, that was like a really dark time, like those four days because you're just, oh, this is going to be the rest of my life. And so, you sit there and you get real religious when you're alone, everybody's religious then. And it's, and it's granted, it's county jail, so it's not like this is, I'm not witness in stabbings and chaos, but it's still jail. And that was November, I get out about a week later and of course there's the depression of the realization of you've thrown your life away. So I looked out because it's first time offender and that was enough for it to give me, you know, let me honor my reconnaissance, and so I started doing stand-up comedy that week. It's open mics at like Florida State this comedy night, so that's December. I plead guilty. My sentence scene is not until June. So now I have six months where I've been told by my lawyer, you're going to prison. How long I don't know. Miltep in this date, the max is five, you're a first time offender, you're young, you're in, you were in school, that all fact, there's points, they take your, your worth in this society is boiled down to character point. Well, you're in school and you have a job. So that's worth four positive points, all but your grades aren't good in school, so that's minus one point. Do told me, I'm going to prison and January, I get a letter from Florida A&M saying I'm suspended from school. Two weeks after that letter, I get a check for $7,000 for financial aid, for classes that I no longer need to take because I'm suspended from school, but my FIA had already been processed for the spring. So I have six months before my life ends, as far as I'm concerned, and I have $7,000. So I just started doing comedy. I used the money from the financial aid check to fund the first six months of my stand-up career. I took the bus to every city you can name in the southeast that had an open mic and I slept in the bus station, I slept on the bus, I slept on city buses, I would get to the comedy club at three in the afternoon because I had nowhere to go. I'd sit at kinkos and do a FedEx office now and do computer work, whatever it just sad out my mind, but I was never happier and I know I'm going to prison and I get to, I get to Senate saying in June, and the lawyers there in five years, you get in five years, that's about that. I just don't see this going any other way. I know this guy and he always goes for the max and you're black and he's going to, and the judge goes, we sentence you to five years pro, patient, and like, the sentence was exactly the way the lawyer put it, five years pre, pro, like the pro, and then he went, oh, patient. And I'm like, wait, that means I go free, right? And I look at the judge, I'm like, does this mean I can kick those, cause I had gigs that week. Does this mean I can kick do a stand-up comedy? He goes, yeah, so long as it's not in the billets, I don't think. And you've been just, for the past six months, you've been freaking out dreading this day. I've been training my day just avoiding it. And so now you get this sort of, it's literally, it felt like my life was handed back to me. And I got blessed with a probation officer that understood how important travel was to my matriculation and betterment as a person, cause generally you're not allowed to travel and just bounce all over the place. But I mean, there were a lot of extra stipulations put down, but I was allowed to travel. How do you go from, you know, you're facing these criminal charges to deciding to do stand-up comedy? Was it just like out of desperation? Well, comedy had always been something I was curious about, even as a child. Like you saw certain people growing out of that. Symbad. Symbad first and foremost. And you saw him and you're like, I want to do that. That's interesting. I wanted to do it, but that's interesting. And then it was Carlin, it was Ron Dale Sheridan and, you know, Eddie Murphy, of course, then stand-up comedy starts coming on TV more regularly, Comedy Central comes online in the mid-90s. And then there's the deaf jam era and then there's BT Comic View. And when I got to college in '96, there was a guy from Birmingham named Ricky Smiley. He's a world renowned syndicated radio guy now. But at that time, Ricky was the first, for me, he was the first Birmingham celebrity. He over there doing it. He from the same place. Huh. I should try that one day. Anyway, you all want some clothes from Dylan, like I was focusing on other things, but - Yeah, but it was in the back here, man. - It's when your free will is about to be taken from you. What would you do if it was given back? - Mm. - You would do the max. - Right. - You wouldn't hedge bets anymore. What do I care about getting booed at a show now? I have no friends, I've been arrested. I'm radioactive socially. No one's hanging with me anymore because oh, my worth was attached to my ability to provide stolen goods to these people. Meet new grippy setting mist from Mavily New York. Gel to mist technology locks in your look for up to 24 hours with flexible all day comfy grip. Just plump, dewey hydrated skin that still feels like your skin. Try new grippy setting mist from Mavily New York. - Maybe it's Mavily. - A lot of people in that situation, they would just go into depression, they would not leave their house, right? Everyone faces hardships, obstacles. They hit rock bottom, right? So how do you use that as like motivation to? I now no longer have any fear, any inhibitions. I could be anything I want. - Nothing mattered. Nothing mattered anymore. I have no friends, I'm walking sad. At a job, I worked at Golden Corral 20 hours a week because I had to be gainfully employed to remain in good status with my probation. So I will do the minimum amount of hours here so I can travel all over everywhere else. - Do you remember the moment you saw like an open mic flyer and you're like, I am gonna go do this? Like what was the first? Lake Ella across the street from Golden Corral. There used to be a little look with a court board with all the community stuff happening around the community. And there was a group in Tallahassee called the Comedy Collage. It was a gentleman named Mike Shader. And Mike was, who's a grad student at Florida State and him and his buddies did stand up comedy around town. So I went and watched the show and off of that, that gave me enough confidence to take the bus to Birmingham to do an open mic and Birmingham. 'Cause I didn't want to debut locally and bomb and Tallahassee's small socially. I don't want to see these people like Golden Corral tomorrow who just saw me suck on stage. - Do you think if you never got arrested that you would have gone into comedy? - No. - If I'd never get arrested, I end up in prison for something worse later. 'Cause the dirt we've been doing was starting to snowball. But I just chose to do this because it gave me a sense of belonging and inclusion. And I knew I wasn't sure I saw my mom. - Let's move forward from here. So it's not like comedy clicked right away for you. You're like trying to build a career and it doesn't quite take off, right? - No, I mean, there are always struggles but there are always small wins and mile markers that let you know, hey, don't quit. - Yeah. - I feel like with this career, I can't speak for every other job 'cause I haven't worked a lot of different industries but I feel like most, I feel like life every year gives you two to three opportunities to skip a level or to prove your worth to whatever, or whomever you pray to, that you deserve another little win under your cell. It's a flappy bird, you know? (laughing) Like, I think it's, you know, for me, you can define it's not going well, fiscally. Of course, no, it wasn't making money. But man, this year I got to open for this guy. And the next year I got to open for an all, man, that was a good year. Now, I also got booed a bunch of times in Atlanta. I was on stage for 30 minutes at top flight until I had to, because the hitliner was late. I was on supposed to do seven minutes but I had to do 30 but I only have 10 minutes of comedy that I wasn't a good night. But oh, damn, my book showed time at the Apollo. Got booed at the Apollo, okay. Oh, but wow, because I did the Apollo, that was enough for me to get the tape audition for the Comedy Central thing. So every year there was just a breadcrum. And there was enough of a pad on the back from the comedy gods for me to never lose faith. Wasn't winning by far, wasn't making money by far, but I never lost faith. You know, doing morning radio at the same time, I come home, I end up at the station, you know. There were working for a lot of people that worked under my pops back in the day. And now I'm co-hosting the morning show. And I do that over the next 10 years. I'm doing prank phone calls and I'm using the prank calls to open up other comedy markets for me. I'm using the pranks, I'm selling CDs after shows. That's giving me money to help stretch a dollar to get a little further. I mean, man, that were days where the gig would cancel on you while you were driving there. And that gig was the gas money home. All right, so now you're stuck in Kentucky. What you gonna do? You definitely ain't calling your mama. And you really ain't got nobody. You can borrow money from it. A couple of people you can, you don't wanna call them with that. So you take it back to high school. You sleep in your car that night. And then you get up the next day and you go to a temp service place and you get a construction job for eight hours. You get the money and then you drive your ass back to Birmingham. And then you continue with your week. And then your mama asked you how to gig. Was your sales good as far? And you never miss a beat. You just improvise and you adapt and you roll with it. And you understand that that night sleeping in the car. I remember one night. And this is the closest I came to quitting. I had a pretty rough patch of shows. There was a booker that accounted for about 60% of my work. 60% of my calendar was booked by this single person who just dominated the South East in terms of stages. And it was one of those choose your self-worth or pay the bills. And I don't know, man, but he caught me on the wrong week. And I chose self-worth. I just told him I wasn't working for him no more. Like he was offering it too low. Well, the truth of it was that. I was told, so in comedy, without going off the rails, comedy is three positions within the show. There's an MC, there's the feature, there's the headliner. So you MC for a couple of years until you prove that you have enough time to feature. When you feature, featuring is interesting because you can host for two or let's just say two, two, three years, one to two years of your prodigy. You host for about three years. Featuring, you could be here, it's like AAA baseball. You may be here two years, you may be here a month, you may be here 15 years. You may never be good enough to headline. But what they always say when your featuring was to go from feature to headliner, you need TV credits. Okay, I would get Apollo and BET's kind of you. All those are black credits, we need more mainstream credits so you can appeal to a broader part of town. I cool comedy central premium blend. I do star search, then I do the big dog, David Letterman. Book Letterman. I did Def Jam and Letterman in the same 12 month stretch. - How old are you? - 2006. - Does it say so? - 25, 25, 26. - Okay, so you've been doing comedy for like six, seven years. Under 10 years in, I've done Letterman and Def Jam in a 12 year stretch. - But you still not financially made it? - No, not financially, but my resume is solid enough for you to be headlining me. Other clubs are headlining me. I'm opening for people who have not had a television credit in this decade. That's unacceptable. And so the book was very much like, yeah, but we'll book you when we can, when we find a spot and they're still featuring me and I keep getting off of headline dates for the weeks that I'm featuring. So I cancel on you because I'm gonna go over here in the headline and they got mad and they told me, we'll give you these dates, but you can't cancel them. I go, I can't promise you I'm not gonna, at the top of the year, they give you your calendar for the year. We can give you some dates, but you better not cancel. I go, I can't promise I won't cancel. We can't give you the dates. All right, cool man, I'll hollage y'all. It's the last time I worked for that company. It's 20 years ago. But at that time, that's how I paid the bills. Was working for them. You made a similar decision later in your career, right? At the daily show. It's the same principle. So for someone in this situation right now, because I know there's so many people that are doing something that they may not love or that they may not feel like they're getting the respect that they deserve. They're not getting treated right. But at the same time, that is their lifeline. Like how do you get the courage to say, I'm gonna stand on my principles here. Choose your form of miserable, but you're going to be miserable. You're going to be stuck and you can figure out other ways to try and jump. I do not believe that every jump is safe. I don't believe that you can always make the seamless transition. Keep in mind, though, I started from a place of I'm going to prison. None of this matters. So I. I always, from the jump, I jumped out the plane without a shoot and then found a parachute on the way down. That's, so whatever that, that hesitation, keep one foot here and stretch over here. I've never behaved like that. - I mean, you've slept in your car. You didn't have to, yeah, I've done it all. I've been to the bottom, so you know what that's like. - But for a lot of people, they don't, they don't know what that's like. You have to decide which discomfort, if you had, 'cause really a lot of it with employment comes down to, I have to work so long doing something I don't wanna do, I don't have the time in bandwidth to even focus and build and create the thing I want to do. So then you need more time. So how do you need less money so that you can have more time? So then you gotta figure out ways to cut bills, cut expenses, and you gotta live lean, you gotta sleep, and you gotta cry in the car. You gotta cry in the car, 'cause you don't have enough gas to run the car at night to keep the car warm enough so you can get to the construction job in the morning. You may have to restructure some things. You have to figure out what you, I really think you have to show the game what you're willing to give up. - So what do you say to that person that is in that point in their life right now? - Well, number one, cry, fill it. When the sun rises, figure out what you're gonna do or what the solution is, you know, I think the most important thing you can do is surround yourself with people that are driven. And if you can't do that, then the next step is figuring out what is the one single thing I can do today to better, to better myself. And that exponentially grows. - And why did you decide to keep pursuing your dream of comedy? - I loved it. I was frustrating, but I loved it. I don't know what else I would do. I don't know if there's anything else I want to do. It's like that, it's like De Niro and Puccino and Heat. He's like, I take scores. I don't know how to do nothing else. I don't know if I want to do anything else. Like this is what I do. But there are days that you don't know what is next and what I've learned over time is that even with some degree of physical success, none of its permanent, all these jobs are temporary. And there's always gonna be a reshuffling. There's always going to be periods of uncertainty. And you just have to understand how to move within the space and trust your ingenuity and your drive will get you there. I found out, you know, for everything that I did in radio, I got fired over, I found on Twitter that I didn't have a job in radio, 2012, I think. I've woke up to tweets from a press release that the company had sent out saying they canceled our show, not even the decency of a phone call to me. And this is after giving 11 years of my life to the city of Birmingham and the community through that station, that's the game. - Take me a step back before I get into this 'cause this is a big chapter. So you book your first big sitcom. What point of your career is this in? - I booked my first sitcom, which was Sullivan and Son. A man Steve Byrne, man, he was the star of that show. And he was good friends with Vince Vaughan. Vince Vaughan was our executive producer. And it was a good show. They didn't want me to produce your statement, but Byrne loved me. And he pushed him, pushed him, pushed for me. But that's also a perfect example of understanding this industry. We got three seasons. And so after every season of Sullivan and Son, we would meet with one of the heads of development at TBS and we would have a dinner. And this is like literally like a week after the finale. We would have a dinner. And season one, we have this dinner. And it's essentially at the end of the dinner after we've had dessert and the check is paid. He goes, all right. Let's do this again next year, which was him basically saying season two. - Right. - It was him basically saying season two on the way. So that was our renewal dinner. We had that at the end of season one. We had the end of season two. And the season three, we have another renewal dinner and we're already planning what we're gonna do next. And man, I can't wait for you. Here's some character ideas for next year. A week later that person left TBS and a new person came in to take over TBS. And he canceled every show except for Conan O'Brien. We were done. I still had my gigs and my bills were paid. And you know, I wasn't in any danger of crying in the car, but I definitely had no sense of direction or bearing of what would be next. But all I knew is that I like doing this. So I'm gonna keep doing it. This is what I like doing. And as long as my career has been, whenever I follow what I like doing, everything goes falls into place on the backside of it. So that's what I'm gonna do. - I mean, that must have been a big year for you 'cause that's also the year you had your son. - Yes. - And then he also booked the daily show. Is that a cloud nine moment or do you remember what that feeling was? - I was in Hong Kong. I was in Hong Kong on a comedy tour doing shows for expats. And I got a call. I don't remember what the time differential was, but it was weird. It was like four in the morning or something where I was. Yeah, man, yeah. 'Cause I had auditioned two weeks prior. I was opening for Wendy Williams. Wendy Williams had a comedy tour at the time. And I'm opening for Wendy and I get a call to audition on a Thursday, but it's a show day with Wendy. And so when you're touring with a headliner, you're not supposed to take off days because you're literally throwing off the chemistry of the show, which makes Wendy's job harder. And I just go to a real humbly. And I looked at the legit. There was no way for me to do it and get back in time. It's just what's gonna happen. - Can I go to the, is it okay if I, because they get a fire at me from the tour, they could just do it and we'll find a new opener to replace you, the rest of the run, but they didn't do that. And that was the money I needed to move to New York, was the tour money from Wendy and she didn't fire me. And I got the audition and I came back and did to finish the tour. I go to Hong Kong to do the shows and then I get the call that I got the show and I had nine days to move my entire life across the country. So what was life? Is this the year that you feel like you finally made it or are you, what are you feeling? - I don't feel like, this idea of made it, it's rock, entertainment is rock climbing. Yeah, you got higher, man, you're way up there, yeah. - So if I fall now, it's even worse. So now I'm really thinking about which thing I do next. And now you had a kid on top of it, made it how? I'm in New York, I've never lived here before. I'm working a super stressful job doing an election year. All the pressure in the world is on Trevor. So it's my job to try and take some pressure off of him to be funny when I get opportunities on stage. And now the kid comes like a couple of months into the employment at the daily show. So now you really gotta make this job work. - And your son was in LA at the time or you hadn't had your son? - He was on the way at the time, he was on the way. So my girl, my girl was pregnant and we're like trying to figure all of that out in the midst of me going to New York and we'll be decided on the front end because with late night television man, casket fired, casket fired all the time. Conan O'Brien was on 13 week contracts the first year. Every 13 weeks, he didn't know if he had another 13 weeks. And so I went into the job grateful but also not sure what would happen. Maybe that's trust issues or abandoning issues or whatever, but I'm not gonna move you in this forthcoming baby to New York until I know for sure what the hell is going on. And so that following spring into the summer, my son is born, I feel a little bit more stable. So you know what, it'd been like a long distance relationship eventually turned into long distance parenting. And then once we got into the fall, I felt solid. And I was like, yeah, this is, I know I'm good. They know I'm good. I feel appreciated. Let's go ahead and move the family all out. Let's merge it up and that's what we did. Where are you feeling, Kilt? You know, just knowing that your dad wasn't there as much and you had your way from your son, like what was that feeling like as a father? I felt guilt, but I didn't also wasn't staying with a whole another family that his mom didn't know about. He'll get older and he'll do the math and understand why I was gone. And even now when I'm gone, I try to talk and send messages to it show him why I'm gone. So it's not the same. I do feel sad because I missed a lot because I was working, even when they moved, even when we moved in in New York. I missed a lot, you know, but those for darn good reasons. I had to make the money. And this show is a golden opportunity. You know, when I sat, one of the first things I did when I got hired at Daily Show, I made a list of everyone that had ever been a correspondent at the time was about 70 people. And we talk about, oh, you do the daily show and it could lead to so many other things. Not for most, statistically it doesn't. Like it ends there, kind of thing. With respect to those people, let me say it in the sense that there are not a lot of correls and cobeirs and sandbees and Jason Jones and Lewis Blacks and Rob Cordries and Al Madrigals and like for everyone that you know who went on to do all of the things. There are a lot of people who didn't do as many things. So how do I not end up like that? How do I go and do all the things? Larry Wilmore, you know, like, so I studied them. Because I didn't want to be left and you know, I wanted to take advantage of this opportunity as much as possible. You know what's interesting is YouTube is a similar way. I actually made a list of all the most popular YouTubers from like 10 years ago or so. And most of them aren't around today. Evolver die. So what is that factor that you learned for those that continue to find success even after a job is gone? Well, the secret first is to thrive where you are. So the secret to thrive and at the daily show was to be as unique as possible in your point of view. And as unique as possible in the physicality of how you deliver something, the nuance of it. It's not so much a gesture opinion. It's not what you say. It's also how you say it. And that was the thing that to me was the delineating factor because for every correspondent that there ever been that is beloved and legendary, no none of them are the same. No single correspondent is even remotely close and overlap. Even if you just took the black ones, if you just took me, Jessica Williams, Dulce Sloan, Larry Wilmore, and Wyatt Sinette. And you just put us all in a room to do a thing. That's five totally different spectrums of blackness. So your uniqueness is your gift. And the goal is to not be like anybody else. And that was the first place I felt where I could be that. And it be rewarded, you know? So it's a dream come true, but it's all temporary. I didn't want to quit, but it makes sense to quit. It makes-- I ain't quitting. I hate that word, but to leave or depart. This must be like one of the best times of your life. I assume, like you're-- That's exciting. It's an exciting time of your life in here. Because you're also an excited. You got the trumpness of it all. Right. The country's evolving and race has become in a huge issue, which is right up my alley again. Right. What year is this? So this is 2016-- well, I got there 2015, but we landed at the show essentially. You know, in the midst of Trayvon Martin protests-- on the backside of Trayvon Martin protests and we're leading into-- you know, that gets into a lot of the police reform in Tony Scott and Rihanna Taylor and George Floyd. And like, once you start going through all-- like there were so many seminal moments, Flandel Castillo, like I was right where I needed to be at the right time to deliver the type of commentary to speak to what was happening in the nation at the time. So yeah, it was exciting. And I'm backed by a crew of creatives that never say no. They just go, how do we make this work and make it funny? And how do we still say something? Like, your ideas aren't stamped out. They're encouraged, they're, you know, floated up. You know, this is when I knew I was at a different job. My second fill piece was about the 20th anniversary of the Million Man March. That is a black segment. Black. And I've been at the show three weeks. And I go to Trevor. Yeah, let me talk to black people about why they mad, about stuff. Is that cool? I could make it funny. I think, yes, go. What was working with Trevor like? He was juggling so many plates, man, because he's running a show. And then I was also still needs to have an opinion every day about everything that's happening, which means he still needs to ingest things, a calm and structured and collect it later. I think the biggest thing I learned from Trevor was about understanding and showing appreciation to everybody and how they contribute to the show. You know, we're talking about a man that would sit sometimes and just be embedded with departments. You go about a graphics department. And Trevor just sit there with the graphics due for no reason for 20 minutes. Just not to give him orders, but to connect. Yeah. And that's a very, very important thing. I think he's a master at that. And also, he was a master at regulating his emotions and how to harness that emotion into humor and not just outrage. I remember we had a-- So the day he was showing those days-- I don't know what they do now-- but in those days, we had a morning meeting where we would convene about the news of the day. And the producers would show you clips from last night. Essentially, there's two conversations. What has happened? What is about to happen? And you decide from both menus what the topics for the show are. Five minutes before morning meeting and the Oscar nominations come out. And it's the year that April Rain denotes the Oscar so light. And Straight Out of Compton does it get like all these movies about enslavement and nominations. But Straight Out of Compton didn't get a nomination. It was a creed or something. There was other movies. Whatever it was, it was ridiculous. The amount of black snubs on the acting and film side. And I met work, Mad, and Trayvon Free who's going on to do amazing stuff. There should be a book about just the writers that are left to show and run stuff. And me and Trayvon in the hall, do you believe it? Man, we got to write something. And Trevor comes up, yeah, let's-- here's how we do it. It's like five sentences. Then he walks off, be a Trayvon. That's funny, all right, let's go. So it changes how you-- I think anger is a very valuable emotion to possess. But I think it's a tool, it's a chisel, and how you use it can be very-- it should never be blunt force trauma. But that's what it was like. It was just watching someone who was an architect of emotion and figuring out ways to quantify so many terrible things for people in a way that made it digestible and understandable. How many years were you at the daily show? Eight years. So this is the most stable period of your life, right? Because you've been just trying to always figure out how to get gas money to go from one place to the next. Even more stable than radio. Because radio, there were a couple of years where I wasn't sure of, and I'm co-hosting it, so it was weird. But yeah, yeah, daily shows are far more-- And you're raising your son? Yeah, I have a kid. You feel like Liza Settle, your mom is proud of you. Yeah, yeah, she's watching those. No more watch party. She got a DVR. Yeah. Yeah, it was good. Those were good times. Yeah. And then Trevor announces that he's leaving the daily show. And at this point, you would even host it for him while he is away. Everybody thought that this was going to go to you. And then you find out that you have to audition for this role. And you do audition for this role. Yeah, but the way it went was Trevor stepped down, fall of 22, he leaves at the end of 22. 23 comes. That entire year, they do guest hosts. And then at the end of that year, in October, they still haven't chosen a host. And were you thinking that that should go to you? Like, was everybody in your ear saying, well, this is going to go to you. Yeah, everybody's going, oh, man, you did real good. And that's the saying you did the correspondence. And so that I'll say this, there was a fair argument to be made for considering me for the chair. OK, fine. There's a more fair argument to be made for House and Menha just well. So it was no secret that a lot of people were wanting and thinking and there were discussions about Chelsea Handler and Sarah Silverman. Because I heard Chelsea Handler. So for whatever House and Rumors, there were, I'd heard more Chelsea than anybody else. But I never thought like, this is mine. You should give it to me. It was just, what are y'all going to do? That's really what the question was. It's been 10 months. What are you going to do? And the response I got wasn't something that I felt gave me confidence in feeling like not only would I be the host or not. But even if I'm not the host, we still don't know. So then the question for me became, well, if you're not the host, then you know your time here is finite. And at the time, the merger had been announced. The merger that's happening now was announced years ago, the intent to sell the company. All right. If I'm not the host, will the new host want me as a correspondent? I don't know. It's plausible. And there's no John Stewart in the conversation at this point when I'm deciding what to do. John, as a matter of fact, he's still under contract with Apple at the time. So-- All right, I'm not the host. That means I stay correspondent. How much longer do I want to be a correspondent? It's a fun job, but If you're gonna do what everybody else did, you're gonna have to leave. So no later, you're gonna have to leave You want to be Carell? You want to be Larry Wilmore? You're gonna. You gotta leave So we gonna leave Roy Well, I don't know Roy. I didn't really thought about that Well, you know if they they hire somebody they may fire you. This is all an internal combo if someone having this with you This is me. Yeah, you're right. They might fire me I mean, they may like you let me keep you around. Maybe they'll keep you through the election yet. Yeah, that's true But man, if I left here Most of the people who leave here leave and host Their own thing San B left got on thing all of her left got on thing prepare Wilmore Jordan Klepper Has had to you know what man? I would really like to have my own thing Well, you know when they normally launch new things right? Yeah, right during the election years So if you want your own thing, you're probably gonna have to leave Yeah, but I don't have no thing set up. Yeah, but to even be considered for your own thing you can't be over here under contract Because in an election year they're not gonna let you out of contact like you like once you sign this new contract my contract was up During this time as well, so I just made the decision. I Want to grow I? Love my time here, but if there's ever a window of opportunity to grow this is it's like when the space show You know in the space shuttle the reentry window you have like This three minutes at this angle and this is the only way to get home Do you have these conversations with yourself? Because I know you've talked about the importance of keeping good company, but it almost sounds like You've got the proverbial, you know angel and devil on your shoulder Is that something that you've always tapped into? Leaving a daily show is one of the first times when I really make that decision on my own I didn't talk with agents or managers or PR people. I was like no, what about you love? I spoke with her before she was the first person I told what was her advice. I told my mom I told my mom I was gonna go see yeah, they asked me to come back for another year, but It was a correspondent So I don't think I'm gonna do it. I think I'm gonna I think I'm gonna just figure it out But I ain't gonna give you the chance tell him to kiss you. I'm like mom This is not about cuss out white people This is me recognizing that For me to grow I have to leave and this is the perfect time to leave I hosted the show I Guess hosted the show and I had a correspondence dinner There's no better time for me to have profile to have an opportunity to go somewhere than right now And if I'm going to do anything anywhere else and at the time James Corden had just left and they had an announcement replacement for Corden yet this is the time And there's all eyes on the show. So it's a cool way to kind of Announce to the world that I'm a free agent. There's an election year coming up And if there's ever new political satirical content, it's launched during election years. It's just like yeah, you're right That was it. How did you tell them I'll tell them through my agents? You know, they sent it all for it's not like I wasn't want it They sent an offer for me to come back as a correspondent and I just told them You know, tell them thank you, but you know, no thanks And that was it and then I sent out a tweet 20 minutes later Like it wasn't a back and forth over days and days and people calling and begging and whatever But the network made it clear that their plan was to continue guest hosting until they could figure out What the actual they we're not in a rush to solve this problem, right? That's essentially what they said They didn't say we don't like you that we're not considering you. It's just This problem will solve it when we solve it I don't work for me. But go So I left and it was no drama. It was hard feelings. It was the last week of the writer's straight And so I went in and I knew the show was coming back online the next week where you know staff would be back And so I went in that Sunday night and I cleaned up my office. I took my son with me He's old enough to understand it just like you know He had been there. He'd see he understood I work in TV that I took him with me when I literally packed the boxes in my office So that he could see and understand that like you work places than you leave places It's not a lesson. He'll get now, but when he's 23 you'll understand and I left And I started writing the book jumping helps you find the parachutes sometimes and I've just been blessed to always find a parachute You know and then three months later I get a call from CNN going hey We're thinking about remaking this British show that's done well for 30 years Would you consider hosting it? It's Natasha Rothbill would say growth So you're no longer the feature now You are the headliner. Yeah, but I had to say no to featuring Disguide having get easier without a parachute over time. No, it's still horrific. I'm a parent Was that was that more scary leaving the daily show than turning down that booker who was 60% of your business? No, it wasn't scary because What I learned from turning down the booker is that if I'm working hard and focused there'll be something else. There's a parachute down there Don't worry. I've jumped before Now what am I gonna do? I don't know. I have no idea But I know staying is not The way because a lot of what's happening now with paramount and stuff like that was what that was my doom today scenario two years ago I was at these new owners coming in and the way they've Cancel co-bear that they would just cut salary at the daily show and like get rid of some and so I had all of these Horrific and I was like and you experienced that at Turner. Yes, and I experienced at the radio station I've had jobs snatched away twice So I'm not gonna wait to know No I'm gonna leave while there's a good window for my shuttle Delan. I think life is a series of peaks and valleys at all his employment relationships all of it I love it. I hate it. It's just about is it net positive for you? Does it make your life better? Does it enrich you? Does it enhance you? I'm not a fatalist in that sense that it's all gonna suck but I am Comfortable in knowing that there will be turbulence on this journey That mean you can't still land the plane but the idea of acting surprised that there's going to be turbulence That's I won't say idiotic, but it's irresponsible. It's disingenuous Very disingenuous earlier. I was asking you about did you feel like you make it and you said that you know I don't know if it's just all of entertainment or life is like rock climbing right where The higher you go further you fall, but there's always more room to climb Like what would be the top of the mountain for you? I thought it was the daily show And I quit it I would love to be able To tell stories and give other people opportunities to tell stories But to me if I could be a beacon to anybody back home in Birmingham that you can be from here and make it But that your ideas matter and that your worth Matters beyond the horizon and or your worth matters beyond any small minded people Who's too scared to go in their dreams Dream chasing That they try to talk you out of your dreams This is a true honor and a privilege Roy. I really appreciate you opening your heart man. This was very heartfelt Thank you. Yeah. Thank you. 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