The Dan Le Batard Show with Stugotz - South Beach Sessions - Deon Cole

Episode Date: August 14, 2025

From being the face of Old Spice, to Black-ish, to Conan, to touring around the country... Deon Cole is everywhere. Deon tracks his career, from not even knowing he was funny... to performing on Conan and immediately earning himself a job there... to the "awkward" through-line of all his characters. He also memorializes his mother, recounting her love and support of him and why he named his special, "Charleen's Boy," after her. With Dan, Deon explores his grief, and feeling her presence during the performance. Deon's latest Netflix special, "Ok, Mister" is streaming now, and you can watch "Average Joe" on BET+. Visit deoncole.com for upcoming tour dates and tickets. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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FX's Alien Earth, an original series now streaming on Disney Plus. Sign up today. 18 plus subscription required TNCs apply. Welcome to South Beach sessions. This man right here, Dion Cole, he is thirsty. Look at that. He is starting, he is ready for everything here. He has done just about everything that there is to do in Hollywood, acting, stand-up comedy, writing, producing. You can catch him on blackish and groanish. You've got a new special out, OK mister, on Netflix, Average Joe on BT Plus, and we'll talk to him about an assortment of other things, including writing. for Conan O'Brien, but thank you for making the time for us here. And thank you so much for having me, man, showing your platform. Among the things that I just mentioned, you enjoy which of them the most, which is the most fun of all the things you've dabbled in in Hollywood?

I think stand up because it's more therapeutic, more personal, you know, it's more of my thoughts. And, yeah, it's more me, you know. I've read you say therapeutic a lot when it comes to comedy. Is it because you're not putting these things? anywhere else you're and so you're you're throwing them at the audience and getting them out in the open is some sort of cleansing for you it really is to be honest with you it's um you know instead of holding all these thoughts in and everything i mean to have someone to talk to about it

or anyone an audience that can understand basically because you could have people close to you and you could talk to them and they just don't get it you know what i mean but an audience of people that get it, that will come to pay to hear you talk in their language, you know, it does become therapeutic because it's like, oh, we all, like an A meeting in a sense, you know, it's similar to that, you know, it's like we're, we all agree with this thought pattern that I have. Well, you, you did an entire special on the passing of your mother, correct? I, I haven't seen that a whole lot in comedy, and I'm assuming that if you're treating this as therapy, that had to be some of the biggest you've done.

Yeah, absolutely. It was very difficult for me to do that. It was on an anniversary of her death. I shot it and didn't mean to, but it turned out that way. Because usually with stand-up, you'll tour, right, but you'll leave one city available where you can shoot a special way, and then you'll go there and shoot that special so you won't tour there. But I went to all these different places and all the venues were booked up.

The only place that was open was this place called Kingston and New York and Brooklyn. That was the only place that was available and I didn't go to Brooklyn. So I was like, all right, let's see what's up. And the date they had available, I was like, give me something towards the end of the month. It was in September. My mother passed September 10th. And so I was like, yeah, give me something. it was the end of the month and they came back with that date the day she did and I was like oh no

I can't I can't shoot on that date but it just kept playing in my mind it was like you know well you should celebrate her on that day and you know keep her alive through your stand-up you know and change the name of your special and just dedicated to her and get these thoughts out and man just put it out there so I changed my whole format of that whole special and yeah dedicated to her man can you take me through and I'll leave this alone in a second but just her being there like what was it does that seem real to you is that is that something that you can believe and have faith in that isn't just in that moment when you're emotional that you carry with you years later does it help you at all with the grief yeah it definitely does because once again

I immortalized her you know and when I was shooting it before I went on stage when I got off stage I cried the whole day man because it was the first year anniversary of that day you know and it was like just like I couldn't do it I was weak at certain parts of that special I wanted to sit down I couldn't stand up I was just like and and I also didn't want that to be a crutch that's why I acknowledged it towards the end of the special what that day was and what I was doing i just wanted to go through the special let everybody see it and then let them know later on you know what it was or whatever but at that moment man i just felt her presence and i'm not just saying i really did i felt her presence and i can hear her almost like saying do it we got you i got

you how about her laughter did you hear her laughter i could feel her man i could just feel her warmth man And then I can feel her going to stop cussing so much. Because my mother always say that. Why you curse so much? I'm going to hear that as I'm doing this special, you know. But, man, it rocked me, though, when I was done shooting it, man. Because, you know, you do those specials, you got to do it twice. You know what I mean?

And then edit it together. So not once did it kill me. I had to go backstage, drop, and then they go show to an hour. Yeah, you're spending. I got to go do it all over again, you know what I mean? And I'm like, rocked, you know. So it was definitely one of the hardest specials I ever had to shoot, but it was also one of the most liberating as well.

What are the landmarks or scars that Charlene's boy? wears from growing up in Chicago. What did that life look like for you early? A lot of love, plenty love, man. I never, we were like, I mean, like every other story that has been told, but we had humble beginnings, very poor, but I didn't even know we were poor like that. Like, I had no idea because it was just so much love and stuff, you know, that she provided. And the food that we ate was really terrible food. But, the way she dressed it up it was like man

this is my favorite you know what I mean like it was like crazy how we would eat like Vienna sausages but that would be like my favorite food you know like ramen noodles was like my favorite so the poverty or the hardship

was disguised from you or you were you were a child and so no one else had anything either so right we have what we have you only have what you have You know what I mean? If you showed me something else, then I would see something else. But if you're showing me this and you're going, this is delicious, this is great.

And I like it and it tastes good. And I'm like, man, this is great. Because that's all that I know. I don't know how to cook as a young boy. I don't know. I'm eating what she provided. And it was delicious. And it was like not knowing that it was like the least of the least is food, you know,

the way she made rice and put ketchup in. it like and I was like this is delicious but it's delicious but that's all we had was rice you know what I mean but it wasn't I didn't look at it like that's all we had was rice I looked at it like yay ketchup and rice again let's go I'm happy you got rice he's got rice again today what else was happening though like what it what else in terms of how funny you were what were the things that were imprinting you so outside of the home it was

you know Chicago Southside Chicago is like like nothing else man it's it's a community

of chaos that's why that's how I like to call this sometimes a community of chaos you got like

drug dealers and pimps and stuff like that but they wasn't like trying to as

as terrible this might sound it's almost like what's that what was what was that what was that

mobster show on we're going to get it together with the guy what's the guy's name you gotta give me Gandalfini oh sopranos

sopranos okay yes so you know how they were just a regular basic family but he was a mob boss but he had kids and he had a home and he had their regular that's how I was in Chicago it was like yeah pimps

did what they did right but outside of that We didn't see that growing up like that. I mean, you saw it, but you didn't. But they were like father figures and, you know, like telling you what to do or not to do. Like, don't do this, stay in school, da, da, da, da, well, it was like that kind of chaos. But controlled, you know what I mean? And even with the gangs, like, if they knew that you was in the arts or sports or something like that, they wouldn't mess with you.

They'd get you a pass. Man, we want you to make it, you know, go do your things. thing or whatever and so it was like I said it was like control chaos in a sense but by living their life and seeing that and then seeing what how everybody else is living in the world it almost made you go oh so these guys oh okay so wow they oh they're not as bad as you would think they are but I get it you know and so it gave you a broad view of everything as far as control chaos as well as trying to make it in the city and trying to be who you are and believing in yourself and having other people believe in you, you know, and pushing you on

or whatever, you know, but the city is a character within itself, you know, and surviving that city and surviving that character, it helps you become who you are, you know. Didn't your mother move you away or try to move you away to get you away from the gangs? And then you ended up getting into fights all the time. So when I was, when we were living around like a gang infested area, I used to, this place called Roseland on the south of the city in Chicago. That's why I was at gang infested all day long. But my mother moved me from there, moved me to the suburbs. I ain't even fight when I was in the city.

When I moved to an all-white suburbs, a suburb called Dalton, Illinois, when moved there, I fought almost every week, these white guys who did racial, stuff and was chasing us and hitting us and burning crosses on our lawn. And I'm like, what is going on? You know, like, what is this? I didn't even do nothing to you, you know. Like, I wanted to go back home and my mother, she worked a lot so she, you know, really didn't see everything. She only saw the aftermath of a lot of stuff. But she thought she was, man, she took her last little money to get this house, you know, and get us to live in a better. And that neighborhood was, it was beautiful, it was nice. It's just the people around it.

It was just chaotic, man, the way that they... And it was just straight racism. They didn't want somebody who was black. And it wasn't. It was straight racism. And then what happened was I started meeting the other black people that are living in that neighborhood. And it was happening to them too.

So we decided to, like, kind of hang out together to. look out for each other, and the more that black people that came out there, kids that came out there, and we saw what's happening than them. We would tell them to come hang with us, and after a while it became like a pack of us, you know, which is my best friends to this day. You know, we hung out together, and then we started fighting back, you know, fighting back and standing up for ourselves and all that. Take me through the fights, though. How many months, how many times? The first ones had to be very, you might be terrified.

The first one, I remember the first one like yesterday. I was, it was just a beautiful neighborhood. And I was like, man, I'm ready to walk to Dairy Queen. I've never even had Dairy Queen in my life. I've seen the commercials, but I couldn't believe it was a Dairy Queen. I'm walking to Dairy Queen. And these dudes pulled up in this Chevy, these white boys, they jumped out the car and just smacked me. I remember that.

And I'm just like, and they're just like, yeah, don't walk over here no more. and then they jump back in the car and left and I'm standing there like what happened? I went back home. I told my mother, she was looking for them. We couldn't find them.

And now I'm like walking around the neighborhood a little nervous and then these dudes it was a bowling alley down the street I was going to bowl and they chased me from the bowling alley and then I went to Arby's one day they wouldn't let me eat in the Arby's.

It was just crazy and I was by myself a lot because my mother had to work, you know? And I'm like, oh, so you're just afraid all the time? I was just terrified, like, wow. And then I met a guy by the name of Dave, and he was just saying like, hey, man, it's a community over here that you can hang out with.

And then we hung out and, you know, it was just cool. We just start hanging out with each other and just like looking out for each other. But it was this one white guy who really looked out for us, too, doing a rich cabars at key that's how i ended up learning about a lot of music like like led zepplin and floyd and we started exchanging music like he one day he hid me in his garage he saw me running right he hit me in his garage and i thanked him for that and his father drove me home and we just started hanging out after that but he didn't know nothing about like hip-hop and i would turn them on like

LL Cool J and Public Enemy and all that, and he was loving it, like, but then he'll be like, man, listen to Fleetwood Mac Lennon Skinner. I'm like, man, they jamming. And we would, that was our relationship to exchange music all the time. I mean, this guy became super cool. You say so casually, though, that I was running and he hid me in his garage. Like, how common a thing was it that you were running through your neighborhood

away from people? like it sounds it sounds terrible it brings me to tears it sounds horrible man I used to man I used to run all the time like they used to just chase us

they chased us but how long are we talking about we're talking about months years man this went on this went on for at least about probably about eight months this went on about probably about eight months until

we're not even eight I'll say probably about like six, about six months because when we moved out there it was like the summertime so it was the entire summer until the schools oh you're not even in school there's got all things to be running so you didn't even want to leave your house

probably want to leave my house what I started doing is I started going back to the city and hanging out with my cousins that's what I would do I didn't even want to stay out there no more like that but I couldn't just not hang out or nothing like that so you know when

school time when it was time to go back to school I had to find a route to get to school and they chased us the route it worked for a little bit and then they found out about our route and they chased us and then after a while there was a guy named Chris

one of my best friends to this day he came out there and Chris was the one I was like no we ain't running no more and Chris was like I remember one time these dudes was like go back to Africa

and Chris was like I was like oh man time to run and Chris was like no take us give us a ride And I was like, y'all, like, I couldn't believe he said that. But then I was like, yeah, man, it's about that time. We fight back.

And I was like, all right, man, the deuce, they pulled up in the car. And they was like, what? And he was like, man, give us the ride if you want us to go back to Africa. And Chris was, like, reaching in his pants. And then they took off. But he ain't had nothing. He was just smart like to do that. But, yeah, man.

Yeah, that was nuts, man. And Dalton's nothing like that now, but, and they used to be so terrifying. Are you wearing a watch? Do you still keep Chicago time on your watch? Like, so you, why do you do that? You see the time? Yes, it's a nice watch. What does it say?

It says 525. Right. What time is it here? It's 225. That's right. Why are you staring me down like that? You're like, I'm sorry. I'm sorry.

It's a Chicago. Oh, it's a Chicago book. You gave me threatening menace for no reason whatsoever. I come in here to talk to a stand-up comic, and all of a sudden I take you back to your child. You're demanding that I read your watch. You're quizzing me aggressively. No, I'll just say, I keep it on Chicago time to keep my mind

in a state of mind, man, in Chicago time. I don't care where I am in the world. I keep that Chicago time. It just, just, I don't know. It just does something to my sight. No, but not I don't know. Like there's, I mean, you're doing something. You're doing something for a reason.

Is it because Chicago is a part of you this way? You don't ever want to forget. It is. It's not even forgetting. It's just it is. It's me all day long. I am Chicago. You see me, anything about me,

know that it's, it's Chicago all day long. And I don't, it's just the way I was brought up, man. It's just, and when you go back to, to that city. As much as I go back, my family's still there and everything. It's just part of my fabric. I can be no other way. You know, so yeah, yeah, that city does something to you.

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by being funny? Like where, where do you, what are the roots of you realizing, wait a minute, I'm, I'm someone who, who has charisma. Right. So it wasn't me. It wasn't me. I hadn't had no idea that I had a funny bone in my body. What I did have by being the only child was an imagination. and I would think things through, throughout. Overthink it, think it, like I would just, because it was always me and I always had to figure out stuff. Like I told you before, my mother worked a lot. My father wasn't around.

I just always had to figure it out. You know what I mean? You were alone. Very, very much. And so I just always thought things out, you know, and I just, to the point where I'll be with some friends and something to happen and everybody might laugh. I wouldn't laugh.

I would try to figure out, that happened. And I would do that all the time. I would be that guy that's, no, wait a minute. Hold on for a minute. Yeah, my friends were, come on, we're going to go get with these girls? What I'd be like, but who are these girls? Like, where where they live at? Where are they from? Do they have fathers? Do they have parents? I would be that guy to the point where people were always to be like, boy, you silly. Boy, you're stupid. And I'd be like, no, I'm serious. And they'd be like, no, you're silly. And one day, a friend of mine named Gwil, he was just like, do you should do stand up.

And I was like, that was the first time anybody having said nothing to me. But you didn't know you were funny? No, not at all. Because I meant everything that I said and everything that I thought of. I meant I wanted an answer for it. It wasn't, and I grew up like that.

I just wanted an answer. And I thought differently about things. I can't say that, but I still wanted an answer for it or wondered why this, that happened. And when he told me to do that, I was like, and then he was like, no, everything. He was like, comics aren't like silly like that. He was like, man, that's a lot of great comedians with just very thought-provoking material. And, like, you're kind of like one of those people.

And he was like, man, you should look up some comedians. So I started looking up people. How old are you? Like 22. And at this point, it's not even, it's never mind on your radar, you don't know you're funny? I don't know it. Nobody never told me I was, ever. All I ever got was, boy, you stupid.

Or boy, you silly. That's Dearn. And no access to comedy as, you're not watching the Tonight Show. You're not, you're, I'm not, I'm not sitting up watching none of it. Now, I love stand-up. I love watching Richard Pry and Rare Fox and Moms. But you, an adult, are you getting access to this as a kid? This is as a kid.

I mean, I got turned on to that by, like, watching Deluxe. You know, Eddie Murphy, and, you know, that's what made me love stand-up. But I wasn't like a stand-up fanatic or going, ooh, I'm going to do stand-up. Like, it was never that. I just enjoyed it. I thought that it was great. But hold on. So at 22, you enjoy it from the first time?

Like, 22, you're told to do is when I first did it. But I knew about stand-up before that. You know, I just didn't think that that was something. Where were you headed in life at this point? Like, what were your career aspirations? What were you thinking about? were you going to make a living before you? I was working out a store called Leathermakers, and I was selling coats.

And my mother was trying to get me to get a job at the CTA, Chicago Transit Authority. And my uncle worked there, and she was like, man, if you can get one of these jobs, they got good benefits, you can drive a bus. It'd be great. And it was. It was a great job. Like, if you worked for the CTA, you knew you made some money, you know? And it was like, man, that's what's up.

And so that's what my mind was. My mind was on selling these coats and that was it and trying to get the job of the CTA. I went to school for like a year and that didn't work out and ended up getting chased home and it was just like

it was a lot of like racism but again but listen listen it wasn't white racism it was like southern racism it was black guys down there that didn't like my fucking from up north

that was like, yo, we don't And I went, oh, God, here we go. I'm running through another. Running through another. They're going to run it again. Damn. Your story's super unusual, though. I can't believe so.

Your friend says to you, you should do this, and there's a bet involved? Yeah, bet me $50 that I do it. We went down to the club for three weeks straight that would let me on. And I just was watching these comedians, and I was gone, I mean, I mean, no disrespect to anybody that's watching,

but I was just like, they're not funny. They're not funny like what I was watching. Like, I was watching Ellen DeGeneres and Mitch Hep, Headburn. I'm watching these guys, and I'm going, they're funny. I'm watching Richard. I'm watching Eddie.

You know, I'm like, man, this is funny. And then I started learning about, like, Bernie Mac and learning about Martin and all these things. other guys that I thought were funny. You know, I was like, man, they're funny. You know, Damon Waynes, you know. I'm like, they're funny guys, you know.

So when I went down to the club and everybody really wasn't funny like that, it was like a couple people that was funny, but that was it. But did you have an act? Like, are you just getting on stage and just? I have wrote five, I have wrote a five minute bit. That's all I did. All I did was took some stories that I told some people before, and I remember them laughing at it.

And I was like, I'm just going to tell some things. I'm just going to tell some things that happened to me that I told some other people before and they laughed at. And so do you know at this point now I'm going to try and do this? How soon does that happen? Like, how am I going to chase this? I like the feeling of this or you're just winning a bet? Nah, I'm just going after the bet. You know, I need the money, right?

So I just want the bet. After I got our stage the first time, because the first three weeks, they won't let me on. after I got off stage there's Adele Givens and George Wilborn they were hosting the show call I mean at a club called all jokes aside when they finally let me on and I got off stage and people were clapping

and the one guy stood up one guy stood up and clapped for me I went home and couldn't sleep I went oh I think I found why I'm here I just kept thinking that to myself. I said, I think I found out why I'm here.

I just kept saying that to myself. I was like, okay. And then I went back again the following week, and I did that same five minutes, and everybody died laughing again. And I was like, okay. And I started talking to other comedians, and they were like, man, you should write another five,

or do this or do that. And I was just like, man, I think I want to keep, doing this. And so I think I wrote like two more minutes. They had these auditions for Duff Comedy Jam at the time. At the time, a lot of comedian were wearing suits. They were in suits because, and this is what was told to me, I ain't saying that this is the true thing or whatever, but they were like, if you weren't funny, at least you look good. You know, so a lot of comics would wear suits and they would look nice and they would be artists. But I never did that.

I think I did it one time, and I was like, I'll never do it again, because it just wasn't me. I was more like a hip-hop cat. And at the time, Def Jam was popping, they were looking for people who had a hip-hop look and that did stand-up. Now, I only got, I only got like seven minutes, right? And I went to audition with the seven minutes. They was like, choose him. Let's get him. He looked nice.

He looked like a hip-hop star, get him. And so by time I aired, I think I had wrote like 12 minutes, right? When I did Def Jam, I did seven minutes, and that left me with five minutes left. They asked me to go on tour. I only have five minutes. And I went up there and bombed on the tour. I think I did like two, two, three dates out of like a 20 city deal, and they sent me home. Because I didn't have enough material because I didn't.

I just didn't know how to do it. Didn't know how to do it. I knew I was, I had, what I had was funny, but I just thought I can keep doing those same jokes and there's like, nah, but I went home and everybody knew that I was on tour and I just wouldn't leave the house because everyone thought I was gone for three weeks. Oh, so you were legitimately hiding in your home because you felt like such a failure that you didn't want to be seen. Right, because it was such hoopla that I was going on tour that I didn't want to be seen.

So when they sent me home, that was the beginning of me going, I need to write. And I believe that's when my writing career started because I started writing unconsciously after that. And how do you get from there to Conan O'Brien? How do you get to writing for that show? So at that moment, I started writing unconsciously. now by the time I came back when I came back out the house and I went to this

and went to perform I'm murdering shit I'm like unconscious with it so now when you say unconscious you like stream of thought like you're just freestyle and just

I got pads of jokes pads of jokes and now I'm like banging these things out that's all I do now I'm writing right and right right right right right right right right it's got named Ricky Smiley

a great comedian a big brother he offered me to come write for him for these prank call CDs I went and did that they blew up he's still getting rich on those CDs that he's doing

and after that I just man just I think I became like a comics comic I really want to sell tickets because I I just wasn't like known like that.

And I was awkward, like weird, but like comics would be like, man, that boy, he could write, you know. And then I started like writing for a lot of people. And then after that, I ended up going to a festival in Aspen. And one of the bookers over there was like Conan's going to be doing the Tonight Show over in L.A. you should be a guest and I was like oh wow great I went on as a guest did my little five six minutes Conan came in the dressing room and Conan came to me and he said did you get good did you get a good parking space and I was like oh you know they got the parking structure we just we just pull in there he was like this but did you get a good parking space and I'm like

yeah it's a parking structure all of them pretty good it was like this did you walk for I'm like, eh, it's all right. He said, uh, you killed out there. I said, thanks, man. He was like, yeah. So is there a long walk back to your car? And I was like, it might be. I mean, I don't think so.

There's a lot of questions about the surface. Then he goes, all right, see you later. And he leaves. And the thing I know, there was like, he wants you ride for him. Well, what was he doing? What kind of interrogation was that? What kind of interview process was that? He was interviewing you and he hired your base.

on you not answering well his questions about how to go, man. So, well, what, you've done well on the show, and you had a job, how soon after that? Like, it was like, it was like two weeks later. Two weeks later, he was, like, what kind of story is this? Like, what kind of career path is this? But none of this man. What are you talking about? I swear, I didn't submit nothing.

I didn't know it was funny. I'm just sitting on television with him. He's asking me part of you was possible. Went, man, that my whole career has been crazy. Anything I ever got, anything I ever auditioned for, I never got, ever. Everything that I've ever gotten happened like that. Any movie, any TV show, I don't care what you bring up. It happens similar to like that.

Like Conan hired me and I went out there and next thing you, I had an Emmy nomination. I'm not playing, man. I'm not making this up. I had an Emmy nomination, maybe like a year later. And then I had another Emmy nomination. And then I ended up getting my own show, just doing these sketches with Conan on his show.

And then next thing you know, I was leaving. Steve Correel and Nancy Correel was putting a show together called Andrew Tribeca with Rashida Jones. And they had me come in and audition as a sergeant. And as I was doing an audition, Steve was looking, was like, well, I don't know if we should have another, like, black sergeant screaming at people or not. Let's just write a, let's write a character for him.

And then there's like, well, what are we calling? I'm calling DJ Tanner. And they'll end up in full house. They were like, yeah, man, I ain't about I going to remember. Just call him DJ Tanner. And he wrote a character. for me on the show. And I began DJ Tano.

Then now I'm on the show that he just was like, man, write a man. Okay, but hold on a second. It's not like you're stumbling accidentally into every place. Take me through when it is you're doing the unconscious writing, the joke that you're filling the journals with jokes

that you realize, because you did go from I think I found my calling, which is a pretty special thing to feel. And now you bomb so you have the failure of learning and you're like, oh, well, if I actually want this, I'm going to have to get good at it. Like, there your lessons are. But what is the period of time that we're talking about here?

How much struggle is in there? How much grind is in there? From the time that, from the time of me being off that tour to the time I got to L.A., that probably was probably about a good 10 years of me just performing, getting down, doing shows, writing, all of that. So 10 years, but have you before or since felt the kind of shame, professionally that you did when they sent you home.

No. Now, I have felt, I have had bad shows. Yeah, you can bomb, but to be sent home because you did two or three times and you were terrible and you're probably more scared the second time than you were the first and you realized what was happening and you're like, wait a minute, what have I got myself into? I've never felt that kind of shame ever again when it came to stand up like that. Everything that I've done, I've done where I can look in the mirror and go, I gave it my best and I and I rock that shit and I think that that was that was good even if it went or if it

didn't go but it produced 10 years of writing 10 years of fuel 10 years of I know this is what I want from that point on I went berserk right and I mean that like I was like couldn't even hold down a relationship because if we were arguing I would go this is hilarious and then I would go nothing was serious focus was singular focus was I have to, I have to, I have to do this. Okay, but so this is the part that's not the stumbling around, though. This is the part, like, with all successful people, people who arrive in places you do, yeah, there can be some luck, but also you were fueled by something that prevented you from having

loving relationships because you knew what you wanted and nothing could get in the way. Right, but this is before Hollywood. So when it comes to Hollywood and where Hollywood and how, and I'm not saying that everything was stumbled. I'm saying that anything I auditioned for I never got because the auditioned and me I wasn't what they envisioned. I just never was and every time I went out for something I always play some kind of like awkward character and everything I ever done. It was an awkward character even my old spice commercials. It's an awkward character blackish, awkward character, Conan, Andrew Tribeca, all of these characters are how I decided to play that character. So when I go to

audition and I decide to put a twist on it, they're going, nah, no, thank you, but no thank you. And I'm going, I think it's hilarious. And then I go. But the people that I met that believed in how I decided to play that character, whatever, they went, man, that's funny. Yeah, I think we can do that. And so therefore, they took a chance on me, and that's how my whole career has been in Hollywood. Before Hollywood, it was me and my pen and me doing these shows around everywhere that I can go perform. I was performing. I had my own nights and I was just writing

to the point where other comedies like, man, we love this guy's writing skills. And that's all I focused on. That was it. Until I had my manager, Kirsten, come and was like, man, I can do something with you.

And she was the one that introduced me to Hollywood. She was the one that was like, man, come out here and audition for this and do this and do that and da-da-da-da and i was like all right cool and then that's when we started that's when hollywood came about but it wasn't i wasn't even thinking about hollywood i just was going from the show to show what's going on with you and awkward though like what is it you you're probably like i guess you've always been a bit askew and how you look at things right like talking to yourself

trapped inside your own head you're even saying i didn't think i was funny i was sort of quirky unusual like and had a different perspective. Why are your characters always awesome? I just, that's just always how I always been. I always been kind of like laugh, a little different, a little quiet, paid attention. Wasn't like, I let a lot of people down, to be honest with you. Because when they meet me, they think that, oh, he's a standup.

He's going to be hilarious. And then I end up being dead serious. And they go, well, he's no fun. You can let down a lot of people that way because the perception of you is like, Oh, he's not. Well, and the expectation of funny is a bitch. But you've been living with it. Exactly.

It's your career, the expectation of fun. See, I rather pay attention to you than make you laugh. You know what I mean? Like, that's the kind of person I am. I'd rather listen. Oh, but that's not comedy. The comedians are more selfish than that. They rather make you laugh that pay attention.

And here we go with Dion being a little different. Because I'd like to listen. I don't want to throw a pie in my face every time you see. me. I want to like hear your world. I'm, I'm all about worlds. Like, I'm, I'm, I'm interested. Like, oh, what did you do today? What happened today? What did you? What, what got you up this morning? So you're not just disappointing people. You're weirding them out. They don't know what to do. They don't know. They don't know what to do with how serious you are, right? Like, is he creepy? I'm cool. I'm cool, but I'm just saying I'm not what they want me to be like that. Like, yeah, I'm just,

You know, I'm just, I'm more like, man, what did you do today? How would you, how was you, you know, how was your word? Oh, you did what today? Oh, how did that happen? You know? Because, again, it's this material thing that imagination, curiosity, and learning something new that maybe I could talk about or whatever. Well, but that's what that, like your curiosity is feeding the machine. If you, if you start listening, then people will unspool for you things that you might not have thought of or whatever.

And if I constantly talk, I'm going to keep bringing up the same thing in order to make you laugh. That's not interesting. Yeah. What's interesting is, hey, what did you do today? And then let's talk about it, you know. And we can talk about me too, but. No, and then I'll take it. I'll steal it from, Drew, and I will make it my material.

And I'll come on here and yell about smiling, stealing my shit, when my whole act is nine things stolen from an awkward conversation. No, listen, I will also, I will be like, hey, I met this guy today. and he said and I'll make it like that or I like to put myself in situations I normally wouldn't be in, you know? And I'll do that too in order to get

material. I just, you know, or whatever. Chris Rock reads like, I heard he reads like seven papers a day. He reads seven papers. You're looking for treasure and looking for stuff and not even not just feeding the brain and then if something happened, it happens. And me, I like, I went to, where did I go?

I went to NASCAR and was just there hanging out. I was running running away from race running around the track I was running around the track no but I went

and I had a great time man I learned so much just about about how they train these guys and be in the pit and like that was amazing to me you know but but if I didn't

if I didn't go I wouldn't have learned about that. You know what I mean? I'd be at home saying the same shit. You know what I mean? So it was good to do that. It's just good to branch out and do different things, you know. And your career for those 10 years is it, you're making enough money to continue to know,

yes, I can keep chasing this. I'm on an upward, you know, trajectory. Yeah, I'm making enough money where I'm happy. And it's a career. You realize, okay, I am doing the thing I've dreamt of doing. Now when you're writing jokes for someone else, and you're writing jokes for someone else who's not very much like you. Yeah, I'm writing for other people and all that.

I'm not thinking about moving up the, and I'm going to be real with you. I never thought about moving up the rail or moving up until I seen other people do it. Other people motivated me. I would be like, oh, he is in a movie with such a such. I just worked in him last week. Maybe I can Maybe I can do that Oh my

He just got a star In the Hollywood Hot Walk of Fame Maybe I can do that Oh wow He just he just got an Emmy Why can I have it It's always been like that

You know what I mean But thinking about I want an Emmy Like I'm I'm caught up into But when do you start dreaming About the things you want I don't know You're at Conan writing for Conan

and you haven't dreamt much beyond that, right? Like you haven't yet, or you're beginning to? I didn't even writing for Conan, I didn't know the magnitude. I wasn't thinking, Emmy. I wasn't thinking none of that. You know what I was thinking? My mother was like, man, again, she was like, those are going to be some good benefits, like health and dental.

Like, my mother had me all on the benefits. She was like health and dental. And so I just was like, because I was about to, quit coning. Like, I was going to quit on it because it just was, it was too mechanic. It was like a mechanical thing. And I'm like, I'm a stand-up. I'm not used to being at work at 7 a.m. I'm going to bed at 7 a. So it's, it's a little boring and it's not as creative as you thought it was and it's not getting different enough, right? Now, it wasn't that. It was, it was the fact that it just, it was, it wasn't me. You know what I mean?

stand-up is me, you know, for me to write for somebody else was, I mean, I did it before, but this was huge. You know, I wasn't even thinking like that. I remember when they were submitting for awards and stuff, I was like, how do you do that? Like, I got to do what? I got to pay to submit for an award. Like, ah, I ain't even how to do that because I wasn't thinking like that. So you don't have any particular affection or allegiance to late night television growing up, right? So you're getting to Conan. And let's not say that. Now, I love the

Tonight Show. Okay. I loved it with Johnny Carson. I loved with Jay Leno. I watched it because I watched guests come on there and Arsenio Hall. I'm deeply sorry I offended you. I didn't intend. I didn't intend to misrepresent

you at all. Okay. So you do like late night. I just thought that perhaps your perspective on late night wasn't formed in the first 20 years and so you see what's happening right now with late night that we're watching it feels like it about to end it feel like to me it feel like it's the end of an era but it has it just needs to be shaken up you know it has to it has to shaking up it has to go with today's times that's what I think I think that it should stay around I think it's just just being

revamped like I me personally I would love to host a late night talk show. It ain't even no black people doing it. I don't even know why. It's like ain't nobody thought to have nobody do this of color. You know what I mean? Just have a different perspective. It ain't no racial stuff.

It's just having a different perspective. You know what I mean? And to have somebody doing that, I still want to do it. And me personally, I don't know exactly how to do it. I had a show called Black Box that followed Conan's show. And it looked at everything that happened a week prior, and we would talk about it. And I remember John Oliver was like, man, we love your show. And then John did the same show and won all kind of Emmys from it, you know?

And man, shout out to John Oliver on that, you know, definitely. But, yeah, I had that idea a while ago when we was doing. You know, the show just didn't keep going for whatever reason, whatever. But, man, yeah, I would love to revamp the late night. for a template of what's going on because right now it's not working at all and it's just this old traditional way of doing it and it's like with all the news and all the podcast and everything that's going on online right now you know everybody has such great content and so interesting things to talk about you know to go sit on somebody's couch and do these bits or whatever It's like, it just needs to be revamped. That's all that I think.

So you were saying, though, I interrupted you. You were about to quit Conan? Yeah, I was going to quit Conan. I was going to quit Conan. Man, like maybe a month and two months in, I was going to quit Conan. You know, I was like, because I wasn't, they wouldn't let me get nothing on. Anything that I wrote wasn't getting on, you know, I didn't fit in like that. But the one thing that made me not fit in

was the one thing that made me fit in because of me not fitting in became a great thing because me and Conan would do this fish out of water thing where any time he has something, I'll be like, what are you talking about? Anytime I brought up something, he's like, what are you talking about? And this became this dynamic that we had

that became comedy gold on his show, you know? And so the thing that made people go, huh, became the thing that everyone had to write for for me. So is this where the awkward comes from, though? Are you always a little bit of an outsider? Have you always felt like a little bit of an outsider? I always felt like an outsider, but it wasn't nothing I'd feel bad about. Oh, no, you're comfortable. Well, but be confident and comfortable in your weirdness.

And anyone's weirdness is a gift. It's like you, you can impart life wisdom principles to somebody by saying embrace your weird. Yeah, it's really, it's just you being you, you know. Like, imagine Jim Carrey being normal. That would be terrible. You know what I mean? It's like, oh, Jim is Jim, man. It's like, man, that's how I feel about myself.

It's like, D is D. Let D.O.B.D., man. So your jokes weren't getting on, though, and you're ready to quit. And so how? And so you find this dynamic, do your jokes end up fitting? or it's just you've got to you got to pivot and the rest of your time with Conan is going to be something else. So real quick, I was very quick Conan, right?

And I was like, after this week, I'm going to quit. I was like, I can't do this no more or whatever. So now I'm not even showing up and writers meetings with ideas. I'm like eating Doritos and shit and they're like waiting on the day to go by, you know. And they wrote this bit and it was called October Fest and I didn't know what it was.

and they were like, yes, it's called October Fest. And I was like, I was like, what's that? And they was like, it's a drinking day. And I was like, that's crazy. And they was like, wow. I said, everybody got drinking day. I said, except black people. I said, you got Cinco de Mayo.

You got St. Patty's Day. I'm like, and now you got October Fest. I was like, that's some bullshit. And they was like, write that up. That was the first time they said, write that up. And I wrote it up and I gave it to Carlton. And Carlton was looking at it. to do it.

And Conner was like, you do it. I'm going to call you out and you do it. And I said, what? He said, I'm going to call you out the curtain and you do it. And I said, when tonight, he was like, yeah. And I was like, okay, like, all right, went out and did it, blew up. The next week, they were doing a Halloween thing because it still was October, and they were talking about hunting houses and what they thought was scary.

And I'm sitting in there again because I'm leaving. right and then about two days I'm leaving and I'm like eating some carrots and I'm like eating these carrots and I was sitting there and they like and they was talking about what's scary in a hunting house and I was like that's I was like I didn't scary to black people

and they was like so what's scary to white people and I was like man like swimming pools and Kardashians a chicken with no sides And I'm just saying all this really racist stuff, right? But then it's like, write, write that up. I was like, what?

And it was like, write it up. And I was like, all right. And I wrote it up, man. And we shot this thing, man, about this hunting house, about me going to a hunter house. And it wasn't scary. And then I was like, this is a scary hunter house. And I'm going to this one house. And then I think the next day,

TV guys said the Starsboard and they wrote that up and then after that we was off and running so after the first time killing it though you're still going to quit you're still at the yeah but after the second time now are you getting a little more of the feeling that you had this is what I meant to do

so after the first one I was going oh okay but I tried to write again and then it didn't it wasn't working they weren't picking up nothing I wrote So now I'm back to, yeah, I'm definitely going to quit next week. And then they started talking about the time of house thing and I brought it up. And after we did it, it was like, okay, we know the formula now.

But how are you feeling now about the choices that you're making? How are you feeling about like what you're going to do going forward? Because now a different kind of performance than stand up is making an appearance and later you would want to do drama and whatnot. So what's being opened here? So now what's being open is there's a fan base that is loving me. And my audience is changing when it comes to my stand-up shows. My stand-up shows are going from maybe 100 seats. You know, I might sell like 400 tickets a weekend in a huge place,

not selling out at all to. selling out now I'm selling out and it's like oh wow okay and so now that's fueling me to keep going and rocking and doing everything then uh conan gets into it with uh jeleno and then we go on tour and the tour just sent me because i was closing out the tour where Conan was closing the tour out but Right before he closed it, I would go last and I would do like 15 minutes worth to stand up. Now I'm on a whole other page because Conan has like Neil Diamond and Eddie Vedder and all these people coming through rocking with him on this tour. Now I'm rubbing elbows with these cats. I can't tell you how inspirational just watching everything you guys did there was to me.

I don't want to bore you with the entirety of the story. but when I had to go out on my own with our company, because we weren't for mainstream media anymore, what you guys did and what he still does, he's going to end up as the most successful of all of those guys, Carson included, because he's going to own all his own shit. He owns all his shit, man. And he's been doing it from the beginning.

He's been doing it. That's one thing about Conan, man. Conan is going to rock with he's going to keep his ear on the street. He's going to keep his ear down to what the kids is doing or what they're part of. He's going to jump in it. He's going to be innovative with his own thing.

And right now, he is slaughtering. It is, but it is amazing, though. I don't think people understand how much work goes into the funny, and in his case, how much neurosis goes into the funny. Like, he always appears and gives off a great deal of happy. But to be

that good over that many decades and to be that still competitive and hungry and motivated, there's something deep inside that dude that probably pushes people really hard, makes his environments, maybe fun and loving, but also difficult because comedy is work and work

is hard. Man, and he instills that in you. He's the kind of guy where you around him and you become funny. You just, you do or you're laughing constantly. There's no in between. Like he when he walk in the room, he'll come and have right now and go.

But you guys, I mean, and would do 15 minutes on how terrible this podcast. And why I shouldn't be here. But he would be hilarious, man. That was the first time I worked for somebody and I realized how insane dude is. You write a joke for him, right? You have to write the joke. Then you have to write deconstructing the joke.

Like, that's how, yeah, like you'll have a bat coming to studio on a string, right? And the bat will go around him and hit be like, oh, these dirty bats are everywhere and there'll be some bit, right? After the bit is over with and everybody live, then we have to go,

look how shitty this bad is, you know? We couldn't get a better string for this. Now we deconstructing a bit. You had to write that too, you know. Or it just comes natural to him, you know, to deconstruct us. So it was, he didn't lead no meat on that bone, man. Well, he's doing the same thing you're doing when you're curious about people and asking all the questions. He's always getting content, right?

People like that, people like you, your mind is always working on how do I stay ahead with the next thing. But so if you had quit before that second skit, where do you think your life go? I have no idea. I definitely don't think that I'll be where I'm at right now. I think I would be doing stand-up, definitely. But those doors that he provided and the magic that we had and all the bits we did and going these soul food together and all these magical moments that we had or whatever led other people. to see that. And I don't think that I would have met the great Kenya Baris who asked me to come right for a project called the Anthony Anderson Project. You know, he asked me to come over there

and write through a woman by the name of Tamar Goings. They were like, come right on the Anthony Anderson Project. And I said, okay, and I went over there to meet everybody to write for them because he saw me writing for Conan. And then the guy that I was going to be writing for whatever, he didn't want to do it no more and he asked me if I could step in and play that character and the show later became blackish that I was going to write for. I went to be a writer

because I couldn't do the show because I was already on Steve Carell show and so I couldn't do this show but the guy didn't do it and Kenya was like can you step in for me like you really are describing a whole bunch of happy actors

I'm not, and look, and look, I would not say this on camera so it could be in the world like this and not be able to verify it. You can ask King of Barrett, you can ask Deke Rehl, you can ask Colonel Bryant, you can ask all of them. And they'll be like, no, it went exactly like that. So what was purposely consciously, consciously something that you desired, chased God? Like, does it exist? Just, is there such a thing of you wanting grabbing, do it? I wanted my own talk show. That's what I wanted.

And it happened, but it didn't stay. That was the one thing that I, and I still wanted. And I'm going to get it. I'm going to get it. I'm going to get it. And I think I got enough funny and enough people that will follow that. And it's going to happen. And like I said, that's one thing that I wanted that didn't materialize, whatever.

Now, something that I wanted, that did materialize, was the specials on Netflix. I wanted that bad. And I was like, I have to get one. And not only did I have one, I ended up getting three, three and a half, really. And so, yeah, that's something that I really, really wanted. And I chase out there and I got it. Black Box was crushing because of what you had poured into it. And it was crushing because.

We came behind Conan and we did the same numbers as Conan did. And they decided not to go along with it because they didn't get it. You got to understand back then, TBS was a baseball network. It wasn't... It's old white people. Old white people. Old white men. Old white men making decisions.

But the content we had and things that we talked about were hilarious still stands up to this day. When people do see little clips or whatever, they're like, man, what happened to this show? And I guarantee you, I want to do a talk show and I want it to be something that's going to be great. I know the formula to do it and it's going to happen. Do you do some of the choices that you make about family purposely? Like are you trying to do family stuff on television or is there? Absolutely. I definitely do.

Like right now I have this podcast that I'm going to start doing called Funny Knowing You. I'm going to be introducing some people and it's going to be. coming out very soon. And it's going to be talk show almost based in a sense. That's a good name. That's a good, it's a good name. Thank you very much. Yes. And it's going to be, it's going to be very, very cool. Yeah, we're going to be launching, I mean, actually be shooting our first episode next week. And yeah, it's going to be really cool, man, talking to some fantastic comics or whatever. And so, yeah, it's going to, yeah, it's going to go, man. It's going to go. Before we get out of

here. What can you tell the people about your 53rd birthday? My 50, well, my 54th birthday, it's, what about it? Well, I thought on your 53rd birthday and a sort of things happened that ended up with you in the hospital and I don't know the back. I don't know the entire. I don't know the entirety of the story. Yes. It sounded like a day that didn't feel very much like a birthday and had had some content in it that would be shitty, awkward, and perhaps funny. Yes, it was, it was, it was, it was, it was, it was, uh, it was a terrible situation that happened, but, uh, I am better now and I'll be, I'll be bringing it up later on. Okay, I brought, okay, fair enough.

I got, we stumbled toward the finish line here. Just, I'm about to run out of here. He's going to be running. through a scared neighborhood somewhere near you soon tell the people about Average Joe on your way out on B2 Plus. It's on Netflix

and it's on B2T Plus. It's called Average Joe. Please watch it. It's a great thriller twist thriller about a guy inheriting some money that he didn't know he had and some guys coming out to him for it and it's not really his and it's crazy. We just shot season two

out in Africa and it'd be coming out. On my birthday, January 9th season 2, but Average Joe is now playing on Netflix and BT Plus. Please check it out and yeah, man. First time as a lead? First time as a lead.

Ain't that crazy. Yes, first time as a lead, man. Number one on car seat. Never had that happen before. Very proud moment. Yes. Congratulations, sir. Happy for all of your success. It was in the light of all you. Platform. You are amazing. Keep doing

what you doing. Thank you. But I didn't feel like I was amazing a couple of times. One, when I got the time wrong on what it was here, because Chicago's two hours behind. I've been thinking about it since it happened. And when Conan came in and told us for 15 minutes, how shitty of a podcast we were doing.

Thank you for being with us. Thank you, man. I've got good news, and I've got bad news. Let's start with the bad news first. The bad news, summer's almost over. The good news, football is back. Better news, it's tailgate season.

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