South Beach Sessions - Deon Cole

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Welcome to South Beach Sessions.

This man right here, here, Deion Cole, he is thirsty.

Look at that.

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 Grown-ish.

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 for us here.

And thank you so much for having me, Mashi, on 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 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?

And so 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 got 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're, we all agree with this thought

pattern that I have.

Well, you did an entire special on the passing of your mother, correct?

Because

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.

I'm 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 stand-up,

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 York and Brooklyn.

That was the only place that 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.

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 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 dedicate it to her and get these thoughts out.

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,

does that seem real to you?

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 her death that day, you know, and it was like just like I couldn't do it.

I was weak at certain 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, but 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 that, 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 I could feel her.

I could feel her going, stop cussing so much.

Because my mother used to always say that.

Say, why you curse so much?

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.

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 two in an hour.

And

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 didn't, 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.

So the poverty or the hardship was disguised from you?

Or you were a child?

And so

no one else had anything either.

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, but that, but this is, 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 you 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 south side of chicago is like

Like nothing else, man.

It's a community of chaos.

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 terrible as this might sound, it's almost like,

what's that?

What was that?

Mobster show

on

the guy.

What's the guy's name?

You got to give me a name Gandalfini.

Oh, Soprano.

Soprano.

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 the regular,

that's how it 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 in the sense, you know, like telling you what to do, what not to do.

Like, don't do this, stay in school, da, da, da.

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'll 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

made you go, oh, so these guys, oh, okay.

So wow, they,

oh, they, 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 Rose in 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 ain't even fight when I was in the city.

When I moved to all-white suburbs, suburb called Dartmouth, 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, what, what is this?

I ain't even doing 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'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.

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 there, kids that came out there, and we saw what's happening to 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, which is my best friends to this day.

You know,

we hung out together and then we started fighting back, you 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 have to be terrified because you're the 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've seen the commercials, but I couldn't believe it was a Dairy Queen.

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,

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 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.

His dude named Rich Gabarzik.

He, that's how I ended up learning about a lot of music, like Led Zeppelin and Floyd.

And we started exchanging music.

Like, he, 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 fleet with mac letter skin

i'm like man they they jamming like 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 that you were running through your neighborhood away from people?

Like it sounds it sounds terrible.

It brings me to tears to be honest with you.

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,

well, not even eight, I 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.

You got all things to be running.

So you didn't even want to leave your house.

I probably didn't 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 that was like, 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, no, 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 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,

man, they used to be so terrifying.

Are you wearing a watch?

Do you still keep Chicago time on your watch?

Like, oh, so you, why do you do that?

You see the time?

Yes,

it's a nice watch.

What does it say?

It says 5.25.

Right.

What time is it here?

It's 2.25.

That's right.

Why are you staring me down like that?

You're like,

oh, it's a Chicago boat.

They 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 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 on Chicago time 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.

It just, just, I don't know.

It just does something to my psyche.

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 that you're.

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 still done everything.

It's just, it's just part of my fabric.

I could be no other way, you know.

So, yeah, yeah, that's that city does something to you.

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Where does the funny come from?

Like, where have you always been somebody who is funny?

Like, is there, were you neutralizing

fights and stuff by being funny?

Like, where do you, what are the roots of you realizing, wait a minute,

I'm someone who has charisma.

Right.

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 would be like, come on, we're going to go get with these girls.

I'd be like, but who are these girls?

Like, where do they live at?

Where are they from?

Do they have fathers?

Do they have parents?

Do they, I would be that guy to the point where people will always be like, Boy, you silly or boy, you stupid.

And I'd be like, no, I'm serious.

And they'd be like, nah, you silly.

And

one day a friend of mine named Gwill, he was just like, dude, you should do stand-up.

I was like.

And that was the first time anybody ever said nothing to me.

But you didn't know you were funny?

Nah, not at all.

Because I meant everything that I said and everything that I thought of.

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 and that happened.

And when he told me to do that, I was like, and then he was like, no,

he was like, comics aren't like silly like that.

He was like, man, it'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 and 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 and nobody never told me I was ever all I ever got was boy you stupid or boy you silly

that's Dion

And no access to comedy as you're not watching the tonight show you're not you're not I'm not I'm not sitting there watching none of it.

Now, I love stand-up.

I love watching Richard Pryor and Red Fox and Mom's Music.

Are 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 Delirious, 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.

What I 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?

How were you going to make a living before you started?

I 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 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 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, it was a lot of like racism.

But

again, chilling.

But listen, listen,

it wasn't white racism.

It was like

southern racist.

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.

I'm running through another.

I'm running through another.

Neighbor running again.

Damn.

Your story is super unusual, though.

I can't believe.

So your friend says to you, you should do this and and there's a bet involved yeah they bet me 50 that i'll 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 ella ellen degenerous and and mitch head head um headburn headburn i'm watching these guys and i'm going now

they're funny i'm watching richard i'm watching eddie i'm you know i'm like man this is funny and then i started uh learning about like bernie mac and learning about uh

uh uh 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 but did you have an act like you are you just getting on stage and just...

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,

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'm 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 a Dale Gibbons and George Wilborne.

They were hosting the show called, I mean, at a club called All Jokes Aside.

And 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,

okay.

And then 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 uh want to uh 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 comedians were wearing suits They were wear 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 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 all this.

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.

Right.

And I want 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 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 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 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.

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

and went and performed,

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 freestyling.

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, write, write, right.

This guy named Ricky Smiley,

a 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

I just wasn't like known like that.

And I was awkward, like weird.

But like a 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 LA

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 could 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 he was like this did you walk far?

I'm like, yeah, it was all right.

He's like, huh.

You killed out there.

I said, thanks, man.

He was like, yeah.

So, is it 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 assistants.

Then he goes, all right, see you later.

And he leaves.

And next thing I know, they was like, he wants you to 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 you based 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 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 i was funny i'm just sitting on television with him and he's asking me path that you sponsor 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 know, we was, I had an Emmy nomination.

I was like,

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 Carrero and Nancy Carrera 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 the audition, Steve was looking and was like,

I don't know if we should have another black sergeant screaming at people.

Let's just

write a character for him.

Will and Dave was like, well, what do we call him?

I was like, call him DJ Tanner.

And they were like, ain't that from Full House?

They were like, yeah, anybody going to remember, just call him DJ Tanner.

And he wrote a character for me on the show.

And I began DJ Tanner.

Then

I'm on the show that

he just was like, man, write a mail.

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,

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 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 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.

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

shame that.

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 gotten myself into?

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 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 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, 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 of you.

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 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.

Conan, Andrew Tribega, 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 or 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 comedians were 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 dah, dah, dah.

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.

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.

Yeah.

Why are your characters always?

I don't know.

I just, that's just always how how I always been.

I 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 stand-up.

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 their 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 like it's your career.

The expectation of funny.

See, I'd 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.

Comedians are more selfish than that.

They'd rather make you laugh than pay attention.

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 all about worlds.

Like I'm

interested.

Like, yo, what did you do today?

What happened today?

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?

Why am I?

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, well, 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.

Well, but that's what it is.

Like your curiosity is feeding the machine.

If you start listening, then people will unspool for you things that you might not have thought of, pretty much.

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.

What's interesting is, hey, what did you do today?

And then let's talk about it.

And we can talk about me too, 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 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.

Looking for stuff, and not even that, just feeding the brain.

And then, if something happens, it happens.

And me, I like, like, I went to uh, where did I go?

I went to NASCAR and was just there hanging out.

And then taste,

running away from

racing.

Running around the track.

No, but I went and I had a great time, man.

I learned so much just about

how they train these guys to be in the pit.

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 to, it's 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, are you making enough money to continue to know, yes, I can keep chasing this.

I'm on an upward

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 the movie with such and 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 Heart Walk of Fame, man.

Maybe i can do that oh wow he just 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 i i'm i'm i'm caught up in but when do you start dreaming about the things you want uh what i don't know you're at conan writing for conan and you haven't dreamt much beyond that right like you 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 Conan.

Like, I was going to quit Conan because it just was, it was too mechanic.

It was like a mechanical thing.

Yeah.

And I'm like, I'm going to stand up.

I'm not used to

being at work at 7 a.m.

I'm going to bed at 7 a.m.

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.

It wasn't that.

It was the fact that it just,

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,

well, how do you do that?

Like, I got to do what?

I got to pay to submit for an award.

Like, oh, I didn't even know 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

Jay Leno.

I watched it because I watched guests come on the air and Marsinio Hall.

I'm deeply sorry I offended you.

I didn't attend it.

I didn't intend to misrepresent you at all of it.

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 feels like to me, it feels like it's the the end of an era.

But

it just needs to be shaken up.

You know, it has to, it has to shake it up.

It has to go with today's times.

That's what I think.

I think that it should stay around.

I think it should just be 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 know exactly how to do it.

I had a show called Black Box that was, that followed Coney'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 kinds 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 podcasts 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, it just, 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?

You were, you were.

Yeah, I was going to quit Conan.

I was going to quit Conan.

And man, like maybe a month, two months 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 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 some, 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, 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?

Yeah, I always felt like an outsider, but

it wasn't nothing I felt bad about.

Oh, no, you're comfortable.

Well,

be confident and comfortable

in your weirdness.

And anyone's weirdness is a gift.

It's like 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, let Dion be Dion, 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 gotta, you gotta pivot and the rest of your time with Conan is going to be something else.

So real quick, I was, I was very quick Conan, right?

And I was like, I was like, after this week, I'm going to quit.

I was like, I can't do this no more, whatever.

So now I'm not 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.

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, 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, except black people.

I said, you got Cinco de Mayo.

You got St.

Patty's Day.

I'm like, and now you got Oktoberfest.

I 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 Connie 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 was October, and they were talking about hunted 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 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 a hunted house.

And I was like, that's, 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 it's like

right 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 hunted house about me going to a hunted house and it wasn't scary.

And then I was like, this is a scary hunter house, and I'm going to something else.

And then I think the next day, TV guys said, A star's born.

And they wrote that up.

And then after that, we were off and running.

So after the first time killing it, though, you're still going to quit.

You're still at the end.

Yeah,

and yeah.

But after the second time, oh, now are you getting a little more of the feeling that you had?

This is what I'm 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 about to, yeah, I'm definitely going to quit next week.

And then they started talking about this Hunting 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

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 opened 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

a hundred 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

Conan gets into it with

Jay Leno.

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 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 Vetter 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 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.

owns all his shit man and he been doing it from from the beginning He's been doing it.

He, 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 and 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, 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 when you're around him, man,

you

become funny.

You just, you do, or you're laughing constantly.

There's no in-between.

Like, he, when he walked in the room, he'll come in here right now and go, but you guys, I mean, and would do 15 minutes on how terrible this podcast is

and why I shouldn't be here.

But he will

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,

like,

you'll have a bat come in the studio on a string, right?

And a bat will go around him and he'll be like, oh, these dirty bats are everywhere.

And then there'll be some bit, right?

After the bit is over with and everybody live, then we have to go, look how shitty this bat is, you know did anybody

we couldn't get a better stream 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 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?

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 to eat soul food together and all these magical moments that we had or whatever led other people to see that.

And I 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 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's 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 it could be in the world like this and not be able to verify it.

You can ask Kenya Barris.

You can ask Deke Rail.

You can ask Colin O'Brien.

You can ask all of them.

And they'll be like, no, it went exactly like that.

So what was purposely, consciously something that you desired, chased, got?

Like, does it exist?

Is there such a thing of you wanting.

grabbing doing?

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 say, and I 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 chased out there and I got it.

Black Box was crushing because of what you had poured into.

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

old white people

and

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'm.

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?

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.

Included.

Yes.

And

it's going to be very, very cool.

And

yeah, we're going to be launching.

I may 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

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, my, well, my 54th birthday.

It's uh

what about it?

Well, I thought on your 53rd birthday, an assortment of things happened that ended up with you in the hospital, and I don't know the background,

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 some content in it that would be shitty, awkward, and perhaps funny.

Yes, 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'm, I'll be bringing it up later on.

Uh, what?

Okay, I brought it.

Okay, fair enough.

We stumbled toward the finish line here.

Just

I'm about to run out of anger.

He's going to be running

through a scared neighborhood somewhere near you soon.

Uh, tell the people about Average Joe on Hackout on B T Plus.

It's on Netflix and it's on BT 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 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 on my birthday, January 9th, season two.

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 Carsey.

Never, never had that happen before.

Very proud moment.

Yes.

Congratulations, sir.

Happy for all of your success.

It was a delightful

platform.

You are amazing.

Keep doing what you're 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 is 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.

But thank you for being with us.

Thank you, man.

We're at the tail end of August, which means summer is almost over.

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