Loading summary
Dion Cole
You're listening to DraftKings Network.
Dan
Look, every football game is a grind and if you're like Dan and the crew, you know there's no such thing as one size fits all. Your sleep should be just as custom as Coach's game plan. That's where Sleep number comes in. You get to call your own plays. Softer, firmer, cooler, warmer. Your side, your comfort. Change it warm whenever you want. No more feeling stuck like a busted play. And for all the late night fights over the thermostat, climate series cools up 20 times faster than the competition. True temp bedding kicks heat and humidity to the sidelines so you can actually stay chill all night long. Bottom line, Sleep number is like having a sleep coach in your corner adjusting to you all night because your best game starts with the right rest. Why choose a sleep number? Smart bed so you can sleep just the way that you like. The only bed that lets you make each side firmer or softer whenever you like your Sleep Number Setting Sleep Number's biggest sale of the year is here. All beds on sale up to 50% off the limited edition Smart bed limited time exclusively at a Sleep Number store near you. Sleep Number Official sleep and wellness partner of the NFL. See store or sleepnumber.com for details.
Dion Cole
Are you feeling more fulfilled now that you're back to work this Friday? No. I need a vacation. See the movie that critics are saying is an awesome look at that crowd pleasing, fist pumping all out brawl of a film. You're right about that. They're coming after our family. Go fix this. Oh my. Nobody 2 rated R only in theaters Friday. Right now at the Home Depot, you'll find storage solutions made to fit your needs. Grab an HDX tough tote to protect your tools or keep your sports equipment contained with reinforced snap fit lids. Or stack up and make better use of your space with bins and totes built to last. Whatever your story, we've got the gear to keep it organized and protected at the Home Depot. How doers get more done.
Host
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 Grownish. You've got a new special out okay Mr. On netflix, average joe on bet 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.
Dion Cole
For us here and thank you so much for having me, man. Sharing your platform.
Host
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?
Dion Cole
I think. I think stand up because it's more therapeutic, more personal. You know, it's more my thoughts and. Yeah, it's. It's more me. You know, I've.
Host
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. And getting them out in the open is some sort of cleansing for you?
Dion Cole
It really is, to be honest with you. 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 can 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 AA meeting in a sense. You know, it's similar to that. You know, it's like we all agree with this thought pattern that I have.
Host
Well, you. You did an entire special on the passing of your mother, correct? 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.
Dion Cole
Yeah, absolute. Absolutely. It was very difficult for me to do that. It was on the anniversary of her death. I shot it and didn't mean to, but it turned out that way. Because usually with standup, you'll tour, right? But you'll leave one city available where you can shoot a special at, 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. Only place that was open was this place called King's Theater in New. That was the only place I 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 towards the end of the month. And they came back with that date the day she. And I was like, oh, no, I can't shoot on that date. But it just kept playing in my mind. It was like, you know what? You should sell it on that day and, you know, keep her alive through your standup, 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.
Host
Can you take me through and I'll leave this alone in a second. But just her being there, like, what was. 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?
Dion Cole
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 her death 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 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. And I'm not just saying that. I really did. I felt her presence. And I can hear her almost like, saying, do it. We got you. I got you.
Host
How about her laughter? Could you hear her laughter?
Dion Cole
I could feel her, man. I could just feel her warmth, man. And I could feel her. I could feel her going, stop cursing so much. Cause my mother used to always say that, why you curse so much? I'd be like, I don't know. So I would hear that as I'm doing this special, you know? But, man, it rocked me, though, when I was done shooting it, man. Cause, you know, you do those specials, you gotta 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 two in an hour.
Host
Yeah, you're spamming.
Dion Cole
I gotta go do it all over again. You know what I mean? And I'm like, rocked, you know? So it was. It was definitely one of the hardest specials I ever had to shoot. But it was also one of the most liberating as well.
Host
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?
Dion Cole
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, viana sausages, but that would be, like, my favorite food, you know, like, ramen noodles was, like, my favorite.
Host
So the poverty or the hardship was disguised from you, or you weren't. You were a child. And so no one else had anything either. So.
Dion Cole
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 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. Cause 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.
Host
It is delicious.
Dion Cole
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 we got rice. We got rice again today.
Host
What else was happening, though? Like, what. What else? In terms of how funny you were? What were the things that were imprinting.
Dion Cole
You so outside of the home? It was, you know, Chicago, south side of Chicago is like. Like nothing else, man. It's a community of chaos. That's how I like to call it sometimes. A community of chaos. You had, like, drug dealers and pimps and stuff like that. But they wasn't, like, trying to. As terrible as this might sound, it's almost like, what's that. What was that mobster show on?
Host
We're gonna get it together with the guy, the guy.
Dion Cole
What's the guy's name?
Host
You gotta give me Gandolfini. Oh, Sopranos.
Dion Cole
Sopranos. Okay.
Host
Yes.
Dion Cole
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 the regular. That's how I was in Chicago. It was like, yeah, pimps did what they did, right? But. 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 in a sense, you know, like telling you what to do, what not to do. Like, don't do this. Stay in school. Da, da, da. Whoa. 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 give you a pass, man. We want you to make it, you know, go do your thing or whatever. And so it was like I said, it was like controlled chaos in a sense. But by living that life and seeing that and then seeing what. How everybody else is living in the world, it almost. It made you go, oh, so these guys. Oh, okay, so. Wow. They. Oh, they 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.
Host
Your mother move you away or try to move you away to get you away from the gang? Then you ended up getting into fights all the time.
Dion Cole
So when I was. When we were living around like a gang infested area, I used to this place called Roseland. Roseland on the south of the city in Chicago. That's where I was at. Gang infested all day long. But my mother moved me from there, moved me to the suburbs. I didn't even fight when I was in the city. When I moved to all white suburbs, suburb called Dalton, Illinois, went and 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 what? 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 just. The people around it, it was just chaotic, man, the way that they.
Host
And it was just straight racism. They didn't want somebody who was black.
Dion Cole
And it wasn't. It was straight racism. And then what happened was I started meeting the other black people that lived 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, their kids that came out there, we saw what's happening in them. And we would tell them, 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.
Host
Take me through the fights, though. How many months? How many times? The first ones had to be very. You might have to be terrified.
Dion Cole
First one. I remember the first one like, it was yesterday. I was. It was just a beautiful neighborhood. And I was like, man, I'm ready to walk to Dairy Queen. I have never even had Dairy Queen in my life. I seen the commercials, but I couldn't believe it was a Dairy Queen in my. Walking the 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 was like, yeah, don't walk over here no more. And then they jumped 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. Cause my mother had to work, you know, And I'm like, oh, so you're.
Host
Just afraid all the time.
Dion Cole
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 started 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. This dude named Rich Gabarzik. He. That's how I ended up learning about a lot of music, like Led Zeppelin and Floyd and. And we started exchanging music. One day, he hid me in his garage. He saw me running, right? He hid 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 him on to, 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. Lyndon Skinner. I'm like, man, they jamming, like. And we would. That was our relationship, to exchange music all the time. And me and this guy became super.
Host
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 terrible.
Dion Cole
It bring me to tears, to be honest with you.
Host
It sounds horrible, man.
Dion Cole
I used to. Man, I used to run all the time. Like, they used to just chase us. They chased us.
Host
But how long are we talking about? We're talking about months, years, man.
Dion Cole
This went on. This went on for at least about probably about eight months. This went on about probably about eight months until. Well, not even eight. I'd 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.
Host
Oh, you're not even in school. You got all things to be running. So you didn't even want to leave your house.
Dion Cole
Probably want to leave my house. What I started doing, I started going back to the city and hanging out with my cousins. That's what I would do. I didn't even wanna 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, nah, 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, nah, take us. Give us a ride. And I was like, yo, Like, I couldn't believe he said that. But then I was like, yeah, man, it's about that time. We. 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 a ride if you want us to go back to Africa. And Chris is, like, reaching in his pants. And then they took off. But he ain't had nothing. He was just smart like that to do that. But, yeah, man. Yeah, that was. I was nuts, man. And Dalton's nothing like that now, but. And it used to be so terrifying.
Host
Are you wearing a watch? Do you still keep Chicago time on your watch? Like, so you. Why do you do that?
Dion Cole
You see the time?
Host
Yes, I do. It's a nice watch.
Dion Cole
What does it say?
Host
It says 5:25.
Dion Cole
Right. What time is it here?
Host
It's 2:25.
Dion Cole
That's right.
Host
Why are you staring me down like that? You're like, suffice. Sorry.
Dion Cole
Oh, it's a Chicago.
Host
You gave me threatening menace for no reason whatsoever. I come in here to talk to a standup comic, and all of a sudden, I take you back to your childhood. You're demanding that I read your watch. You're quizzing me aggressively. No, I'll just show you. I said I keep it.
Dion Cole
I keep it on Chicago. I have to keep that 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. I don't know. It just does something to my psyche. No, but not.
Host
I don't know. 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 your.
Dion Cole
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 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 that city, as much as I go back, my family's still there and everything, it's just part of my fabric. I could be no other way, you know. So yeah, yeah, that city does something to you.
Dan
Look, every football game is a grind and if you're like Dan and the crew, you know there's no such thing as one size fits all. Your sleep should be just as custom as Coach's game plan. That's where Sleep number comes in. You get to call your own plays. Softer, firmer, cooler, warmer. Your side, your comfort. Change it whenever you want. No more feeling stuck like a busted play. And for all the late night fights over the thermostat, Climate series cools up 20 times faster than the competition. True temp bedding kicks heat and humidity to the sidelines so you can actually stay chill all night long. Bottom line, Sleep Number is like having a sleep coach in your corner adjusting to you all night because your best game starts with the right rest. Why choose a sleep number? Smart bed so you can sleep just the way that you like. The only bed that lets you make each side firmer or softer whenever you like. Your Sleep Number setting Sleep Number's biggest sale of the year is here. All beds on sale up to 50% off the limited edition Smart bed limited time exclusive at a Sleep Number store near you. Sleep Number Official Sleep and Wellness partner of the NFL. See store or sleepnumber.com for details.
DraftKings Announcer
UFC 319 hit Chicago for the first time in six years. Bet the card with DraftKings sportsbook, the official sports betting partner of the UFC. New customers bet just five bucks. Get 200 bucks in bonus bets instantly. We've got a banger of a main event. We've got Dricus du Plessis vs Khamzat Chimaev for the middleweight world title. It's going to be be crazy. Don't miss out on all the UFC 319 action. Download the DraftKings sportsbook app now and use the code BEACH. That's code BEACH B, E, A, C H for new customers to get 200 bucks in bonus bets instantly. When you bet just five bucks only on DraftKings, the crown is yours.
Gambling Announcer
Gambling problem. Call 1-800-GAMBLER in New York, call 877-8-HOPENY or text HOPENY and 467369 in Connecticut. Help is available for problem gambling. Call 888-789-7777 or visit ccpg.org Please play responsibly on behalf of Boot Hill Casino, Kansas, 21 and over. Age and eligibility varies by jurisdiction.
Dion Cole
Void.
Gambling Announcer
In Ontario, bonus bets expire seven days after issuance. For additional terms on responsible Gaming Resources See DKNG CO AUDIO where, where does.
Host
The funny come from? Like, where have you always been somebody who is funny? Like, is there what you. Were you neutralizing fights and stuff by being funny? Like, where, where do you. What are the roots of you realizing? Wait a minute, I'm. I'm someone who has charisma, right?
Dion Cole
So it wasn't me. It wasn't me. I 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 happened and everybody might laugh. I wouldn't laugh. I would try to figure out why 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 like, come on, we gonna go get with these girls. What? I'd be like, but who are these girls? Like, where they live at, where they from? Do they have fathers? Do they have. Do they have parents? Do they. I would be that guy to the point where people would always be like, boy, you silly, or boy, you stupid. And I'd be like, no, I'm serious. And they'll be like, nah, you silly. And one day, a friend of mine named Gwil, he was just like, dude, you should do standup. I was like, that was the first time anybody ever said nothing to me.
Host
But you didn't know you were funny.
Dion Cole
Nah, not at all. Cause 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, 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, you kind of like one of those people. And he was like, man, you should look up some comedians. So I started looking up people and how old are you like 22?
Host
And at this point, it's not even. It's nevermind on your radar. You don't know you're funny.
Dion Cole
I don't know it. And nobody never told me I was ever. All I ever got was, boy, you stupid or boy, you silly. That's Deion.
Host
And no access to comedy as you're not watching the Tonight Show. You're not.
Dion Cole
I'm not sitting there watching none of it. Now. I love standup. I love watching Richard Prior and Red Fox and Mom's movie.
Host
An adult. Are you getting access to this as a kid?
Dion Cole
This is as a kid. I mean, I got turned on to that by like watching Delirious, you know, Eddie Murphy and, you know, that's what made me love stand up. But I wasn't like a standup fanatic or going, ooh, I'm gonna do standup. Like, it was never that. I just enjoyed it. I thought that it was great.
Host
But hold on. So at 22, you enjoy it from the first time? Like 22 you're told to do is when I first.
Dion Cole
First did. But I knew about stand up before that. You know, I just didn't think that that was something.
Host
Where were you headed in life at this point? Like, what were your career aspirations? What were you thinking about? How were you gonna make a living.
Dion Cole
Before you stepped down? Was working at 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 they was. My uncle worked there. And she was like, man, if you can get one of these jobs, they got good benefits, you could 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 a job at the cta. I went to school for like a year, and that didn't work out. Ended up getting chased home. And it was just like. It was a lot of, like, racism. Oh, but listen, listen. It wasn't white racism. It was like Southern racism. It was black guys down there that didn't. Like motherfuckers from up north that was like, yo, we don't. And I went, oh, God, here we go.
Host
I'm running through another. Running through another neighborhood, Running again.
Dion Cole
Damn.
Host
Your story's super unusual, though. I can't believe so Your. Your friend says to you you should do. And there's a bet involved.
Dion Cole
Yeah, he bet me $50 that I'd do it. We went down to the club for three weeks straight that wouldn't let me on. And I just was watching these comedians and I was going, I mean, no disrespect to anybody that's watching, but I was just like, they not funny. They not funny. Like what I was watching. Like I was watching Ellen DeGeneres and Mitch Hedburn. Heburn. 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 start learning about, like Bernie Mac and learning about Martin and all these 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 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.
Host
But did you have an act like, are you just getting on stage and just.
Dion Cole
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.
Host
I'm just gonna tell some things.
Dion Cole
Just gonna tell some things that happened to me that I told some other people before and they laughed at.
Host
And so do you know, at this point now I'm gonna try and do this. How soon does that happen? Like, how am I gonna chase this? I like the feeling of this. Or you're just winning a bet.
Dion Cole
Nah, I'm just going after the bet, you know, I need the money, right? So I just want the bet. After I got off stage the first time, because the first three weeks they wouldn't let me on. After I got off stage, it was Adele Givens and George Wilborn. They were hosting the show called, 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 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, like, okay. And then I started talking to other comedians and they was 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 Def Comedy Jam. At the time, at the time, a lot of comedians were wearing suits. They were wearing suits because. And this is what was told to me. I ain't saying that this is the true thing or whatever, but. But they were like, if you wasn'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 like seven minutes. 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 the 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 had five minutes. And I went up there and bombed on the tour. I think I did like two, three dates out of like a 20 city deal. And they sent me home. Cause I didn't have enough material. Cause I just didn't know how to do it. Didn't know how to do it. I knew I had what I had was funny, but I just thought, I can keep doing those same jokes. And they was 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.
Host
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?
Dion Cole
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. Cause I started writing unconsciously after that.
Host
And how do you get from there to Conan o'? Brien? How do you get to writing for that show?
Dion Cole
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 perform, I'm murdering show. I'm, like, unconscious with it.
Host
So now when you say unconscious, you like, stream of thought. Like, you're just joke freestyling.
Dion Cole
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, writing, writing, writing, write. This guy named Ricky Smiley, great comedian, 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 wasn't selling tickets because 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 gonna be doing the Tonight show over in la. You should be a guest. And I was like, oh, wow, great. I went on as a guest, did my little five, five, six minutes. Conan came in the dressing room, and Conan came to me and he said, did you get. Did you get a good parking space? And I was like, oh, you know, they got the parking structure. 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. He was like this. Did you walk far? I'm like, eh, it was all right. Nah, you killed out there. I said, thanks, man. He was like, yeah, so is it a long walk back to your car? I was like, it might be. I mean, I don't think so.
Host
It's a lot of questions about the suit.
Dion Cole
Yeah. Then he goes, all right, see you later. And he leaves. And next thing I know, they was like, he wants you to write for him.
Host
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 you based on you not answering well his questions about how to go, Man, Man. So, well, what? You done well on the show and you had a job. How soon after that?
Dion Cole
Like, it was like. It was like two weeks later. Two weeks later.
Host
He was, what kind of story is this? Like, what kind of career path is this, but none of this, man. What are you talking about? Swear.
Dion Cole
I didn't submit nothing.
Host
I didn't know I was funny. I'm just sitting on television with him, and he's asking me for you.
Dion Cole
Sponsors went, man, my whole career has been 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 know, we was. 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 Carell and Nancy Carell was putting a show together called Andrew Tribal with Rasheeda Jones. And they had me come in and audition as a sergeant. And as I was doing auditions, 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. Let's just write it. Let's write a character for him. Will and Dale's like, what we call him. I'm sorry, call him BJ Tanner. Now. They ain't up from Full House. They was like, yeah, man, nobody gonna remember. Just call him DJ Petter. And he wrote a character for me on the show, and I began, DJ Tanner then. Now you. Now I'm on the show that. He just was like, man, write a meme.
Host
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. A 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 gonna have to get good at it. Like, there your lessons are. And. 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?
Dion Cole
From the time that. From the time of me being off that tour to the time that I got to LA, that probably was probably about a good 10 years of me just performing, getting down, doing shows, writing, all of that.
Host
So 10 years. But have you before or since Felt the kind of shame professionally that you did when they sent you home?
Dion Cole
No. Now I have felt. I have had bad shows.
Host
Yeah, you can bomb. But.
Dion Cole
But. But. But to shame that.
Host
To be sent home because you did two or three times and you were terrible, and. 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 gotten myself into?
Dion Cole
Never. Never felt that kind of shame ever again. 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 rocked that shit. And I think that that was good, even if it went or if it didn't go, but it produced 10 years.
Host
Of writing, 10 years of fuel, 10 years of, I know this is what I want.
Dion Cole
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, right? Nothing was serious.
Host
Focus was singular.
Dion Cole
Focus was, I have to. I have to. I have to. I have to do this.
Host
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 but this.
Dion Cole
So when it comes to Hollywood and what 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 audition and me, I wasn't what they envisioned. I just never was. And every time I went out for something, I always played some kind of, like, awkward character. And everything I ever done, it was an awkward character. Even my Old Spice commercials is an awkward character. Blackish, awkward character, Car, 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 going, nah, nah, 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 is back. 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 comedians, 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, 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. 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 show to show.
Host
What's going on with you? And awkward, though. Like, what is it? You probably like, I guess you've always been a bit askew in 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.
Dion Cole
I don't know. I just. That's just always how I always been. Always been kind of like, left 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. So you can let down a lot of people that way, because that perception of you is like, oh, he's not well.
Host
And the expectation of funny is a. But you've been living with it like your. It's your career, the expectations.
Dion Cole
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 rather listen.
Host
Oh, but that's not comedy. Those comedians are more selfish than that. They rather make you laugh than pay attention.
Dion Cole
Here we go with Dion being a little different because I 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. I'm all about worlds. Like, I'm. I'm. I'm interested. Like, yo, what did you do today? What happened today? What. What did you. What. What. What got you up this morning?
Host
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. Do with how serious you are. Right. Like, is he creepy? Why am I cool?
Dion Cole
I'm cool, but I'm just saying I'm.
Host
Not what they want me to be like that.
Dion Cole
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 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, content, and learning something new that maybe I could talk about or whatever.
Host
Well, but that's what that. 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, whatever.
Dion Cole
And if I constantly talk, I'm gonna keep bringing up the same thing in order to make you laugh. Oh, 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.
Host
But no, and then I'll take it. I'll steal it from you, and I will make it my material. And I'll come on here and you yell about smiling, stealing my shit, when my whole act is nine things stolen from. Awkward conversation.
Dion Cole
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.
Host
You're looking for treasure, looking for stuff.
Dion Cole
And not even that. Just feeding the birds. And then if something happened, it happens. And me, I like. Like, I went to. Where did I go? I went to NASCAR and was just there hanging out.
Host
Running away from. Running away from racing.
Dion Cole
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 to be in the pit. And, like, that was amazing to me, you know? But 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. It's good to do that. It's just good to branch out and do different things.
Host
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.
Dion Cole
Yeah. I'm making enough money where I'm, I'm happy, so.
Host
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.
Dion Cole
Yeah. I'm writing for other people and all that. I, I'm, I'm not thinking about moving up the. And I'm gonna be real with you. I, 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 the movie with such and such. I just worked with him last week. Maybe I can. Maybe I could do that. Oh, my. He just got a star in the Hollywood Walk of Fame. Maybe I can do that. Oh, wow. He just got an Emmy. Why can't I have it? It's always been like that. You know what I mean? But thinking about, I want an Emmy. Like, I'm caught up into.
Host
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.
Dion Cole
I didn't even writing for Conan. I didn't know the magnet. 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 gonna 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. Cause I was about to quit Conan'. Like, I was gonna quit coning because it just was. It was too mechanic. It was like a mechanical thing. Yeah. And I'm like, I'm a standard up. I'm not used to being at work at 7am I'm going to bed at.
Host
7Am so 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.
Dion Cole
It wasn't that. It was the fact that it wasn't me. You know what I mean? Standup is me. For me to write for somebody else was. I mean, I did it before, but this was. Was huge. You know, I wasn't even thinking like that. I remember when they were submitting for awards and stuff, I was like, well, how do you do that? Like, I gotta do what I gotta pay to submit for an award. Like, ah, I ain't even had to do that. Cause I wasn't thinking like that.
Host
So you don't have any particular affection or allegiance to late night television growing up? Right? So you're getting to Conan and.
Dion Cole
Oh, let's not say that. No, I love, I love the Tonight Show.
Host
Okay.
Dion Cole
I loved it with Johnny Carson. I loved Jay Leno. I watched it because I watched guests come on there. Okay. Arsenio Hall.
Host
I'm deeply sorry I offended you. I didn't attend it. I didn't intend to misrepresent you at all. So you. 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 do you see what's happening right now with late night that we're watching? It feels like it about to end.
Dion Cole
It feel like to me, it feel like it's the end of an era, but it just needs to be shakened up, you know, it has to shaken 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 being revamped. Like 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 to 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 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 podcasts and everything that's going on online right now, everybody has such Great content and so interesting things to talk about. To go sit on somebody's couch and do these bits or whatever, it's like it just, I just, it just needs to be revamped. That's all that I think. The Disney Plus Hulu HBO Max bundle plan starting at just 16.99amonth.
Host
No one will ever break us apart.
Dion Cole
Catch Marvel Studios Thunderbolts the New Avengers on Disney. You can't escape the past. Alien Earth on Hulu. This ship Collected monsters and Final destination Bloodlines on HBO Max. Death is coming for our family. The Disney Plus Hulu HBO Max bundle plan starting at $16.99 a month. All these and more streaming soon. Visit Disney plush, Hulu hbomaxbundle.com for details.
Gambling Announcer
This episode is brought to you by LifeLock. Between two factor authentication, strong passwords, and a VPN, you try to be in control of how your info is protected. But many other places also have it, and they might not be as careful. That's why LifeLock monitors hundreds of millions of data points a second for threats. If your identity is stolen, they'll fix it, guaranteed or your money back. Save up to 40% your first year. Visit lifelock.com podcast for 40% off terms apply.
Host
So you were saying, though. I interrupted you. You were about to quit Conan. You were. You were.
Dion Cole
Yeah, I was going to quit Conan. I was going to quit Conan, man. Like maybe a month, two months in, I was going to it call, you know, I was like. Cause 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. Because of me not fitting in became a great thing because me and Conan would do this fish out of water thing where anytime he has something, I'll be like, what are you talking about? Anytime I brought up something, he like, what are you talking about? And this became this dynamic that we had that became comedy gold on his show, you know, so the thing that made people go, huh? Became the thing that everyone had to write for, for me.
Host
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?
Dion Cole
I always felt like outsider, but I. It wasn't nothing I felt bad about.
Host
Oh, no, you're comfortable. Well, be confident and comfortable in your, in your weirdness. And anyone's weirdness is a gift. It's like you. You could impart life wisdom principles to somebody by saying, embrace your weird.
Dion Cole
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, is like, D is D. Let D. Let Dion be Dion, man.
Host
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 gotta. You gotta pivot, and the rest of your time with Conan is gonna be something else.
Dion Cole
So, real quick, I was, I was. Gary quit Conan, right? And I was like. I was like, after this week, I'm going to quit. I was like, I, I, I can't do this no more. Whatever. So now I'm not even even showing up in writers meetings with ideas. I'm, like, eating Doritos and shit. Just in there, like, waiting on the day to go by, you know? And they wrote this bit, and it was called Oktoberfest. And I didn't know what it was. And they were like, yeah, it's called Oktoberfest. And 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, why? I said, everybody got drinking day. I said, sup, black people? I said, you got Cinco de mayo. You got St. Patty's Day. I'm like, and now you got Oktoberfest. 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 Conan. And Conan was looking at it to do it. And Conan was like, you do it. I'mma 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 was October, and they were talking about haunted houses and what they thought was scary. And I'm sitting in there again because I'm leaving, right? And in about two days, I'm leaving, and I'm like, like, eating some carrots. And I'm, like, eating these carrots. And I'm sitting there, and they like. And they was talking about what's scary in the haunted house. And I was like. I was like, that ain'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. Chicken with no sides. And I'm just saying all this really racist stuff, right? But then they, like, right there 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 haunted house, about me going to a haunted house, and it wasn't scary. And then I was like, this is a scary haunted house. And I go into this haunted house. And then I think the next day, TV guys said, a star is born. And they wrote that up. And then after that, we was off and running.
Host
So after the first time, killing it, though, you're still gonna quit. You're still at the end, 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.
Dion Cole
So after the first one, I was going, oh, okay. But I tried to write again, and it didn't. It wasn't working. They weren't picking up nothing I wrote. So now I'm about to. Yeah, definitely gonna quit next week. And then they started talking about this haunted house thing, and I brought it up. And after we did it, it was like, okay, we know the formula now.
Host
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 standup is making an appearance. And later you would want to do drama and whatnot. So what's being open?
Dion Cole
So now what's being open is there's a. There's a fan base that is loving me, and my audience is changing when it comes to my standup shows. My standup shows are going from maybe 100 seats. You know, I might sell, like 400 tickets a weekend. And 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 Conan gets into it with Jay Leno, and then we go on tour, and the tour just sent me. Cause I was closing out the tour. Well, Conan was closing the tour out. But right before he closed it out, I would go last, and I would do, like, 15 minutes worth of stand up. Now I'm on a whole nother 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.
Host
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.
Dion Cole
He owns all his shit, man. And he been doing it for. From the beginning, he 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 gonna keep his ear down to what the kids is doing and what they're part of. He gonna jump in it. He gonna be innovative with his own thing. And right now, he is slaughtering.
Host
Slaughtering. 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. 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. 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.
Dion Cole
And. And he instills that in you. He's the kind of guy where you around him, man, 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 in here right now and go, which guys. I mean. And would do 15 minutes on how terrible this podcast is and why I shouldn't be here. But he will and be hilarious. 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. Like, you'll have a bat come in the studio on a string, right? And a bat'll go around him, and he'll be like, oh, these dirty bats are everywhere. And it'll be some big. After the bit is over with and everybody laugh, then we have to go, look how shitty this bat 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, and. Or it just come natural to him, you know, to deconstruct it. So it was. He didn't leave no meat on that bone, man.
Host
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 goes?
Dion Cole
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 standup, definitely. But those doors that he provided and the magic that we had and all the bits we did and the going to eat 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 Barris, who asked me to come write 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 Tamara Goines. They were like, come write 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 write Conan. And then the guy that I was gonna be writing for, whatever, he didn't wanna 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's show. And so I couldn't do this show, but the guy didn't do it. And Kenya was like, can you. Can you step in for me? Like, you really are describing a whole.
Host
Bunch of happy actors.
Dion Cole
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 Barris, you can ask Steve Carell, you can ask Conan o'. Brien. You can ask all of them, and they'll be like, no, it went exactly like that.
Host
So what was purposely consciously something that you desired changed? Chaste got like, does it exist? Is there such a thing of you wanting, grabbing, doing?
Dion Cole
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 want it. And I'm gonna get it. I'm gonna get it, I'm gonna get it. And I think I got enough funny and enough people that will follow that and it's gonna have happening. 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 after I got it.
Host
Black Box was crushing because of what you had poured into.
Dion Cole
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.
Host
It's old white people. Old white people, old white men.
Dion Cole
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 be 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 gonna happen.
Host
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 absolute.
Dion Cole
I definitely do. Like, right now I have this podcast that I'm gonna start doing called Funny Knowing youg. I'm be introducing some people and it's gonna be coming out very soon and it's gonna be talk show almost based in a sense. But that's a good name.
Host
That's a good. That's a good name.
Dion Cole
Very much, yes. And it's gonna be. It's gonna be very, very cool. And yeah, we're gonna 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. It's going to go, man.
Host
It's going to go before we get out of here. What can you tell the people about your 53rd birthday?
Dion Cole
My 50. My. Well, my 54th birthday. It's. What about it?
Host
Well, I thought on your 53rd birthday, an assortment of things happened that ended up with you in the hospital. 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.
Dion Cole
Yes, it was. It was. It was. It was. It was a terrible situation that happened. But I am better now and I be. I'll. I'll be bringing it up later on.
Host
Okay. I brought. Okay, fair enough. 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.
Dion Cole
Your way out on bt. It's on Netflix and it's on bt. It's called 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 after him for it. And it's not really his and it's crazy. We just shot season two out in Africa and it'll be coming out my birthday, January 9th, season two. But Average Joe is now playing on Netflix and BET. Please check it out and. Yeah, man.
Host
First time is a lead.
Dion Cole
First time as a lead. Ain't that crazy? Yes. First time as a lead man. Number one on car seat. Never, never had that happen before. Very proud moment. Yes.
Host
Congratulations, sir. Happy for all of your success.
Dion Cole
It was a delightful platform. You are amazing. Keep doing what you're doing.
Host
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.
Dion Cole
Thank you, man.
Podcast Summary: The Dan Le Batard Show with Stugotz – South Beach Sessions featuring Deon Cole
Release Date: August 14, 2025
The episode begins with Dan welcoming comedian Deon Cole to the “South Beach Sessions.” Dan highlights Deon’s diverse background in Hollywood, including his roles in popular TV shows like Black-ish and Grown-ish, his stand-up comedy, and his work as a writer and producer for Conan O'Brien.
Dan: "This man right here, Deon Cole, he is thirsty. Look at that. He is starting. He is ready for everything here." ([02:33])
Deon Cole expresses gratitude for being on the show, thanking Dan and the platform for the opportunity.
Deon Cole: "For us here and thank you so much for having me, man. Sharing your platform." ([03:02])
Dan probes into Deon’s passion for stand-up comedy, asking which aspect of his multifaceted career he enjoys the most. Deon reveals that stand-up is particularly therapeutic for him.
Deon Cole: "I think stand up because it's more therapeutic, more personal. You know, it's more my thoughts and. Yeah, it's. It's more me." ([03:13])
When pressed about the therapeutic nature of comedy, Deon elaborates on how performing stand-up allows him to express and cleanse his thoughts in a way that feels communal, likening it to an AA meeting.
Deon Cole: "It does become therapeutic because it's like, oh, we all like an AA meeting in a sense. You know, it's similar to that." ([04:18])
Dan brings up Deon’s notable stand-up special centered on the passing of his mother, a deeply personal and uncommon subject in comedy. Deon recounts the emotional turmoil of shooting the special on the anniversary of his mother’s death.
Deon Cole: "I could hear her almost like, saying, do it. We got you. I got you." ([06:12])
He describes feeling his mother’s presence during the performance, which provided him with strength but also led to intense emotional moments post-show.
Deon Cole: "I could feel her warmth, man. And I could feel her going, stop cursing so much." ([07:14])
Deon shares memories of his childhood in Chicago, emphasizing the love and humble beginnings despite financial hardships.
Deon Cole: "Lots of love. Plenty love, man. I never. We were like. I mean, like every other story that has been told." ([08:21])
He details the transition from a gang-infested area in Chicago to a predominantly white suburb in Dalton, Illinois, where he encountered overt racism, including physical confrontations and hate crimes.
Deon Cole: "Damn. But my mother moved me from there, moved me to the suburbs." ([12:44])
Deon describes the constant fear and necessity to defend himself, leading to the formation of a close-knit group with other black youths who supported each other.
Deon Cole: "It was this pack of us, you know, which is my best friends to this day." ([14:39])
At 22, motivated by a bet from his friend Gwil and facing repeated rejections from comedy clubs, Deon embarks on his stand-up journey. Despite initial struggles, including being banned from multiple venues, he perseveres.
Deon Cole: "I went up and bombed on the tour. I think I did like two, three dates out of like a 20 city deal." ([29:15])
This phase becomes a turning point as Deon transitions from performing stand-up to focusing on writing, eventually catching the attention of other comedians and landing writing gigs.
Deon Cole: "After that, I just wouldn't leave the house because everyone thought I was gone for three weeks." ([32:13])
Deon narrates how his dedication to writing led him to write for Conan O'Brien after an impromptu interaction during a guest appearance.
Deon Cole: "He was like, yes, you kill it later. And I'm on a whole nother page because Conan has, like, Neil Diamond and Eddie Vedder and all these people coming through." ([58:11])
He emphasizes Conan’s innovative approach and the rigorous process of joke creation and deconstruction that influenced his own comedic style.
Deon Cole: "You have to write the joke. Then you have to write deconstructing the joke. Like, that's how it is." ([60:00])
Deon discusses his self-perception as an outsider and how it shapes his comedy. He prefers to listen and be genuinely interested in others rather than forcing humor, which sometimes leads to others perceiving him as serious or weird.
Deon Cole: "I'm all about worlds. Like, I'm interested. Like, yo, what did you do today?" ([42:51])
This unique approach fuels his comedic material, allowing him to explore diverse topics and maintain a distinct voice in the industry.
Deon shares his aspiration to host his own late-night talk show, advocating for more diversity in such platforms. He critiques the traditional format of late-night shows and expresses a desire to revamp them to reflect contemporary times and diverse perspectives.
Deon Cole: "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." ([48:42])
He envisions a talk show that embraces different viewpoints and pushes the boundaries of conventional late-night formats.
Reflecting on his journey, Deon illustrates how persistence and embracing his unique comedic style led to significant breakthroughs, including Emmy nominations and roles in major TV shows.
Deon Cole: "I'm making enough money where I'm happy." ([45:31])
He credits his manager, Kirsten, for introducing him to Hollywood and facilitating opportunities that aligned with his authentic self, despite initial setbacks and rejections.
Deon touches upon personal experiences, including a challenging birthday that led to hospitalization, hinting at future discussions around it.
He also announces his upcoming podcast, "Funny Knowing You", aimed at introducing fellow comedians and fostering conversations akin to a talk show format.
Deon Cole: "It's gonna be a talk show almost based in a sense." ([64:56])
Additionally, he promotes his role as the lead in "Average Joe" on Netflix and BET, celebrating this milestone in his acting career.
Deon Cole: "First time as a lead man." ([67:13])
Therapeutic Nature of Comedy: Deon Cole uses stand-up as a means to process personal trauma and connect with audiences who understand his experiences.
Resilience in Face of Adversity: Overcoming systemic racism and personal hardships in Chicago shaped his comedic and professional journey.
Transition from Performer to Writer: Initial struggles in stand-up led Deon to focus on writing, eventually securing a pivotal role in Conan O'Brien's show.
Authenticity and Unique Voice: Embracing his outsider status and genuine curiosity fuels Deon's distinctive comedic style, setting him apart in the industry.
Future Aspirations: Deon aims to innovate late-night television by introducing more diverse perspectives and plans to launch a podcast that mirrors a talk show environment.
Deon Cole on Therapeutic Comedy:
"It does become therapeutic because it's like, oh, we all like an AA meeting in a sense." ([04:18])
Deon Cole Reflecting on His Mother:
"I could feel her warmth, man. And I could feel her going, stop cursing so much." ([07:14])
Deon Cole on Late-Night TV Diversity:
"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." ([48:42])
Deon Cole on Persistence and Success:
"I'm making enough money where I'm happy." ([45:31])
This episode of The Dan Le Batard Show with Stugotz offers an intimate look into Deon Cole's life, exploring how his experiences have shaped his unique approach to comedy and his trajectory in the entertainment industry. Through candid conversations and heartfelt reflections, listeners gain insight into the resilience and authenticity that drive Deon's success.