I just announced all my tour dates.

It's called the High and Mighty Tour.

I'm coming to Washington, d c Norfolk, Virginia, Madison, Wisconsin, Milwaukee, Wisconsin, Detroit, Michigan, Cleveland, Columbus, and Cincinnati, Ohio, Denver, Colorado, Portland, Maine, Providence, Rhode Island, Springfield, Massachusetts, Chicago, of Course, Indianapolis, Indiana, Louisville, Kentucky, Albuquerque, Masa, Arizona, Kansas City, Missouri, Saint Louis, Missouri, Minneapolis, Minnesota, Nashville, Tennessee, Charlotte, North Carolina, Durham, North of Carolina, Saratoga, California, Monterey, California, Modeesto, California, and port Chester, New York, Boston, Massachusetts, Portland, Oregon, and Seattle, Washington.

I will be touring from February through June, So go get your tickets now.

If you want to come see me perform, I will be on the High and Mighty Tour.

Hi Catherine, Hi, Chelsea.

How are you.

I'm wonderful and you're in.

An Arctico right now.

I am in the Southern Hemisphere right now.

I am hiding in a closet recording this introduction to you.

I can't tell you what's going on yet because I'm going to download everyone when I get back.

So it has been transcendental.

Well, since everybody is dealing with Thanksgiving stuff, we'll get right into it.

But our guests today had a great book.

I really loved it.

You know, our guests today from The Daily Show and CNNs.

Have I got news for you.

He is here to talk about his new book, The Man of Many Fathers, Life Lessons disguised as a memoir.

You're listening to Roy Wood Junior on this episode of Dear Chelsea, and I have to say, let me tell you something, Roy.

From a woman to a straight man, it is.

So refreshing, Catherine, I think you would agree to read a book by a straight man that is so reflective and self aware, and it was really just such a great book, like thank you for women to read and for mothers to read about how to raise a good man.

I think there's a lot of stuff in here about that and your relationship with your mother more specifically, and your relationship with your father.

So let's start there with your relationship with your father, because you didn't really start out living with your father.

Your mom and you you guys lived alone for a while, and then you started to get into a little bit of trouble, and she decided to move so that you could be close to your father.

So she essentially got back together with your father in a kind of open relationship because you started to act up.

Yeah, now that I'm older, I can say I don't think she ever got back with him.

She moved in.

We moved back in with them, which is a different dynamic because they never slept in the same bedroom like my parents, never as far as I know, ever had sex again.

But the idea of I'm a single mom, I work all day, I'm in grad school all night.

I cannot keep an eye on him.

I will lose him to the streets if I don't make this choice.

So in a lot of ways, I think that my mother sacrificed her own happiness and comfort in a way to ensure that I had some degree of upbringing having a male in the house.

So you guys moved to Birmingham right when you moved back in with your father.

Okay, correct, they're great.

So but you talk in the book.

We're going to jump around a little bit because in the book, since you just brought it up in the book.

You talk about your dad's other you know, he had children with another woman, He had two young sons with another woman, and you talk about her coming over to your mom's house or your parents' house, and your mom flipping out and being like, as long as I don't see any of these women, it's okay, but don't bring them around here, which implies that they were in some sort of romantic relationship.

No, yeah, I guess some sort of open relationship, or you're disrespecting me because I'm your wife, but you have kids, and you take this woman out all over town to the point where people thought that was my mom, Like anytime I Pop stepped out, it was with her, And so for my mom, I think it was I know what's happening, but I'm gonna keep my head down.

The money I'm saving on rent, I'm pouring into law school, and then I'm gonna fucking leave you.

In the meantime.

These women are not gonna be so blatant with the disrespect that they think that they can just come over to your house and say hello to you or check in with you and things like that.

And so that's where my mom drew the line.

My mom is very gangster man like, I just think that it's not a part of herself that she likes to access.

I mean, she went toe to toe Jim Crow in Mississippi in the sixties.

She was the first wave of students to integrate Delta State University, a university that, as of recent is in the news because of two black people Bey found hunged.

So she's talked a lot of shit to a lot of people in strange places and could have paid a much larger price.

So no, she's not gonna be scared of some random woman coming to the house trying to cuss my daddy out.

You gonna get You're gonna get slapped up.

Well, she's gonna come back with a bat, is what happens in the book.

Yeah, my bat and I couldn't even use it anymore.

And littlely after that because the glass ended.

That's a separate conversation.

Well yeah, yeah, you can read about it in the book.

Everybody.

My mom was just very no nonsense, And I don't know how that changed my look on relationships.

I definitely know how it changed my look on marriage for sure.

Like I don't have an idealistic view of marriage I'm not anti marriage, but you're not gonna tell me everybody that is married is successful and truly happy.

So don't throw these thirty year forty year relationships in my face as an example of what could be.

You know, forty years, how many happy mm hmm.

And that's the question Mary, people never answer, right.

Right exactly.

It's kind of like when you talk about raising a child.

I mean I find it analogous to that only because I've done neither of those things.

When you think about raising a child and all the things that come along with it, it's like, how many moments of bliss are there?

Obviously you love.

This person more than anything else in the world, But how many moments of bliss compared to the moments of stress and agony and all of the other things that come with it?

And how how do those moments of bliss just overpower all of the other stuff?

You know, it's kind of similar to marriage, like it can't be.

I guess it has to be more good than bad.

But raising a kid, you know, if you get an if you get an off one or one that's not cooperative, that's fucking stress.

Or really unload on me either.

Yeah, nobody wants to raise the murderer.

No, and I'm sure they didn't set out to do things that made their child commit crimes.

But with my son, I'll say this, it feels like an opportunity for me to create the version of myself that I wish I had been, and then to set that out into the world to better the world, if you will, that idea of it.

You know, I'm not really caught up in legacy or not.

Like I didn't name him Roy Wood the third.

I wouldn't dare that would be really embarrassing.

It's also a love letter to your son in a way.

It's telling your son what you missed.

And I think what you're saying is also it's really powerful for fathers to talk to their sons in this way, especially you know, as men, because the language, you know, the softer the language becomes, and the more insightful it becomes, the less violent the world becomes.

You know, raising a guy is tricky.

Yeah, let's talk a little bit about your relationship with your father.

This guy was like a major communicator.

You say some very funny things about him, but he was very influential.

He was on the radio, he was part of the civil rights movement, right.

Yeah, yeah, I'd say a civil rights journalist is probably the best way to somebmate.

Like he's just a journalist who focused solely on struggling conflict on issues affecting black people globally.

And when you expect time with him, like in the book, it sounds like you were kind of like he just kind of took you wherever he went.

You were kind of his little sidekick, right like, and he wanted to keep you occupied.

He didn't want you out on the streets.

He wanted you to either be in class.

I mean, in one instance, he enrolled you back in school after you've had already finished your school year because he didn't want you hanging around the house, which I think is a clutch move.

Actually, he didn't even enroll me.

He just took me to the school because I would spend the first when Memphis City schools ended, I get sent to Birmingham.

First month in Birmingham, Birmingham City Schools are still in session, So rather than get a babysitter, he just dropped me off at it.

Knowing what I know now, it's probably some teacher he was fucking and like damn, you know how good.

Your dick games got to be to just hey, put my son in your class and teach him shit, I'll be back at three.

And that's what he would do.

Man, My pops would take me around with him and I never got to go do put or have a fun cool father.

It's literally, hey, man, Jesse Jackson's in town for the Democratic National Convention.

I'm gonna go interview him.

You're coming, bring a snack, and that was it.

And if you could pay for it yourself, even better.

Because his dad was hugely penurious, didn't want him to spend any money.

So Roy, like myself, was very resourceful as a young person, creating his own business raking leaves, drumming up a lot of business.

Also, we have something in common, which I texted you about last week, is in the book he tells.

One of my favorite stories, or the one that resonated with me the most, because there's actually a lot of similarities between our childhoods, is that your parents forgot to pick you up from school and you walked home in the freezing cold.

How long did it take you before you got a ride from that guy at the convenience store.

It was a liquor store.

It's way worse than you wish.

It was a convenience store.

I was walking forty minutes before I got to the liquor store, and I still had about another hour to go to get home.

And what was the temperature it was?

It was about fifteen degrees maybe twenty.

It's Birmingham in January.

Baseball season starts late January.

Both my parents thought the other one was going to get me from practice.

I get home and they're fucking watching Jeopardy, just chilling like life is sweet.

And I get into the liquor store and there was just a drunk dude in there, and I'm like, hey, man, just will you give me a ride?

Like he offered the ride, and I'm you know how you like you talk those in that era in the nineties, don't take a ride from a stranger.

I'm like, fuck it, bro, even if you're gonna molest me, I bet you got a heater, so let's do it.

And the guy, God bless him, was a drunk, but he cared enough to cap the liquor and not drink and drive while he took me home.

I know that was a very nice touch to that story.

You think it's almost a misdirec.

You think he is going to molest you, and instead he's like, you know what, I'll save my drink.

It's a laughter.

I get this kid home.

Yeah, he's like, I'm a drunk, I'm not a pervert.

I was like, I respect that, bro.

Yeah, I appreciate that.

But that's the kind of community Birmingham was.

Man, It's just strangers would still look out.

There was still Southern hospitality.

It's just it's a fifteen year old kid shivering to his bones.

Give him a ride.

I told you my parents once did that to me.

They forgot to pick me up from Hebrew School.

And I walked home two and a half miles in a snowstorm, and I immediately I was conn I just walked in.

I saw them the same thing.

They're sitting at the fucking kitchen table.

I was the youngest of six kids, though, so like my parents, both of them together had six children, and so I guess that's some sort of excuse of being just fucking too many, bankrupt of you know, time, emotion, or any sort of logistical planning.

But yeah, I walked in pissed and I was like, fuck both of you and Roy when I texted Roy this.

I was like, I also got left at school, and he said, did you call the cops on them?

I'm like, yeah, as soon as I got home, I called the police.

I was the only child in that house with my parents.

How y'all not notice that I'm not here yet?

Now, the fact that they both each thought the other was going to get you, but neither of them looked at each other and was like, where's Roy when they got home.

Yeah.

But see, that's the thing.

My parents didn't really like completely like rock with each other like that, So if they were in the same room watching TV, they just had to enjoy that moment of peace.

I could understand my mom not looking at him and going, hey, don't forget responsibilities, and then my dad snapping on her about something.

You tell a story about being a kid and getting in an argument with your mom over a toy that you wanted at the moment, and then your mom was like you started to kind of throw a tantrum, and your.

Mom just walked out and left you there.

And then a white woman got involved, somebody who was scared for your safety.

So I want to know in what other ways have trifling white women impacted your life.

Roy, you know what, that white lady was trying to help, but she didn't know she was interrupting an important lesson about discipline, because my mama was one of the ones where I'll just leave you.

I'm not going to argue with you if you want to have a temper tantrum about a fucking voltron lion, I'm just gonna leave you in the mall.

And my mom walked off from the poor little white lady.

Miss you left your son, miss like she knows that was the whole point of it.

I remember one time getting separated from my mom in the fifth grade and having a panic attack in Macy's in the galleria and a white lady comes over and sir, what's going on?

And I'm gonna I'm gonna help you, And what's going on?

Baby?

What's your mother's name?

George?

Come over here?

And this fucking white cashier, Chelsea, pulls up the PA system in Macy's and hands it to me.

And then I'm just on the my mama, where are you?

I'm the women's stockings this Roy click and my mom comes over furious, cusses out the white lady.

My mom is one thousand percent in the wrong.

But my mom is framing it under some sort of I knew where he was, he knew to stay there, you need to mind your business.

But because in my mom's mind, it's they're going to take you from me.

Yeah, right, that's all.

That's all her thoughts were was that you called the police.

You called you have involved an employee, who will involve management, who will involve the police.

So my mom had to come in on the offensive and just immediately like cuss her out like that.

That's that's really the most really weird white women that there was a semi racist incident in Tallahassee with a partner in mind, But like, is it racism?

If they're right?

What's which a partner here?

What do you mean a partner?

Ask you?

Well, I'm not the one to answer that, roy as you know, but what was the other experience?

So in college, me and a partner we went to the mall.

We're like seventeen years old, maybe eighteen, and we walk into Wilson's the Leather Experts.

You have to say the full name of this store.

We go into Wilson's and we're just looking at leather jackets.

White woman's sales rep comes over.

She goes, we don't have Layo Way.

We haven't said shit, She hasn't said hello, how you doing shit?

Can I help you?

My name is whatever, And we go we don't need Leo Way, and we snapped back at her real fast, and she walks off.

And then we looked at the price of it jackets and fucking we need it.

Layaway them shits.

It's like a it's a level jacket.

It's just like starts at one thousand dollars.

We thought this would be one hundred and fifty dollars, like fucking starter jacket, like some NBA Jordan Chalcolne.

It was one thousand dollars.

So me and Barrett spend the next thirty minutes in the store pretending we have money because we don't want her to think we don't have money, because that's how you fight racism.

It's just aggressive browsing.

So's just kept trying on shit.

Let's circle back to your dad.

So how do you look at your relationship with your dad now that you're an adult man with a son, Like, how do you frame it and how do you feel about it?

I think forgiveness without forgetting it's probably the best bucket to put it in for however, our parents failed us, be it mom or Dad.

You get older and you start looking at some of them and I can draw lines to go ahe that's why you did that, That's why you behave like that.

That sucks, but at least I understand now.

One of the biggest blessings for me was doing finding your roots, and I did that, you know, the DNA show or whatever, and they find out all of this history about my dad's side of the family that I never knew was my dad never brought me around his side of the family, only like family reunions, and I know my half said, I know all my half siblings, but his extended family tree never met him.

So I found out that my grandfather was killed when my dad was four what he disappeared in the night without a trace in Georgia in the nineteen thirties, so we know what that is.

The census data that PBS found showed that my father did not have another male head of household the rest of his life.

So for all I know, he didn't have a version of what I had growing up, just somebody there to check his ass and he also was hit by a car when he was sixteen and crippled permanently while running after a woman that had just broken up a girl, because he was sixteen running after a girl who had just broken up with him.

So how do you think that informed his idea and opinions about women and dating and who was there to give him any type of game on manhood?

Truth be told, I walked away from that television show that day just understanding that my pops was pretty much fucked from age four and was solidified at age sixteen.

And anything else he became, he became as a byproduct of trying to get past whatever traumas he was still dealing with.

So you comfort yourself and women, I guess, but you comfort yourself and the people you know that praised you and adore you.

You know, he was loved for his voice because he couldn't be athletic anymore, and you know, he changed a lot of people's lives.

I think that's the part that's like so weird when you have a parent that was different for you than what everybody else got.

Because you know, my Pops dies when I'm sixteen, and then you start hearing all these cool stories and great stories about him, and I didn't get that.

I never saw or experience that.

One of the hardest things for me to do is I follow my two younger siblings.

My two young I'm closest to them because we're closest in age, and with me and the older halfs it's a twenty year age gap up.

So like with the younger ones, one of the hardest things is following them on social media because they'll post pictures with them and Pops and they got the old school polaroid Kodak joints to have the date printed on the photo, and I can look at the photo and look at the date and tell you whether or not the lights were on at our house or they're at disney World or they're at damn six Flags.

My little brother post a picture me and Daddy that summer when we went to the thing and we had a good time, and I'm like, I had to fucking sit and watch you interview Michael Ducaccus in eighty four, like I didn't get to go to nothing fun.

And then on top of that, you're beefing with my mom at the time, but you're living the normal life over there.

And after a while you just got to respect it, Chelsea, like, it's not ideal, it wasn't cool.

But as I got older and I had a son, and I started thinking about the idea of showing him love and what does love look like?

And well, what were the examples I had of love?

I have to look to my dad and the other woman.

I have to and I have to unpack that if if I want to have any shot of understanding how I would show up in love with a woman, I need to look at how my dad showed up, so I have something to compare and contrast my behaviors to.

And that was ie opening because I mean, you know my stand up, I don't talk about my life.

I don't talk about but because it was just so weird, it was so complicated, it was easier for me to just talk about the world.

But you know, I look at the choices he made, and I really feel like my pops didn't understand how to get love right until the end, until like the last ten years of his life.

So you go around, I'm the ninth of eleven kids by five different women.

Just for perspective, so you spend a front half of your life and career dedicated to the job that you love, but also running from this commitment and your responsibly just you know, having kids all over the place, and I start unpacking that, and I look at it to a degree, and it feels eerily similar to my pattern.

Separate.

I mean, I don't have a bunch of kids all over the place.

But and you don't have two partners.

I mean, I bet you wish you did, but you don't, not that I know of.

Do you have two partners?

I tried to set you up sexually a couple of months ago, but I don't know if that panned out or not.

That person would not want two partners either, Just so you know that.

No, I have one child that I co parent with with his mom, and that's that's great.

I've I love what I do, and I think part of it where I feel like there's similarities between me and my dad is comedy is the one place that makes me feel alive.

Entertaining and writing and creating.

Everything else fall second.

So when there are huge respect abilities and big things that I have to take care of, I might all runs not the right word, but I'm anxious avoiding that shit to the end of the day or the end of the week or the end of the month if I have to.

So, you know, comedy as an escape from something you know, or does it fulfill you.

I don't know what the difference is, but I feel like Radio meant that to him, which is why he was so superb at it, which is why he helped so many people while he was doing it.

I did the White House Correspondence dinner and afterwards, just random black people are come, yeah, you're dad.

In nineteen seventy one got me in my first Pepper Bard and I remember I needed a tape recorder and we was at the Presca and your daddy loan meet his audio and like, it's just these He loved what he did.

And also, I think to a degree, just ran from everything else.

So you know, you have to unpack with your parents or if you're going to figure out who you are and what the best parts of them are so that you can take that and pass that on to your children.

You open the book by saying, trying to raise a child before healing your inner child is a motherfucker.

So where what do you feel like you've healed your inner child?

Getting there?

Oh?

Guess what I bought About a month ago, I bought that same black Voltron lion that I was crying to my mom about in Memphis in the eighties, and I saw it.

I saw it at like a collectible story.

I was like, yeah, I might, I'm gonna get that fucking lion.

Now I don't.

I don't have it.

On one of these days, it'll it'll make it to this shelf.

But the idea of you know, I have a responsibility to my son, so I'm not here to play video games and watch baseball all day.

But I do feel like there's a degree of joy and fun that I lost because I had to worry.

I had to rake leaves, I had to cut deals in the neighborhood because I didn't know when the next argument was going to happen between the two of them, and he wasn't going to pay a bill, and then the gas is off or the heat is off, you know, the electricity.

You know, my mom was working her ass off to jobs in night school and law school and grad school.

I don't want to bother her with needing fifty dollars for the sneakers or the field trip.

So I'm gonna hustle.

So yeah, I missed out on a lot of things.

Yeah, I missed out.

I missed out on a lot of things because because I had to grow up a little faster.

Right you know.

Yeah, being a latchkey kid when you were growing up is probably, well not probably, it's a lot different than it is today.

And what it means today.

Oh, it's illegal.

Not what we were doing.

Oh, they would have taken me away from my mom in her heartbeat.

First of all, let's talk about your almost threesome that you had getting a home.

Is that how you're classified?

That's how I classified it.

Yeah, why don't you tell us that story.

It's one of those things though, where like here's the thing they tell kids, Hey, be careful, don't let nobody touch you in your area, right, like make sure no one touches your breast.

They never tell you how pervert spit gain?

Is that?

Is that a better way of putting it?

Like the groom, Basically, you say, when somebody really wants to go out of their way for you or do you a favor and they're too eager to do it, watch out.

Don't trust them.

And I'm like that to this day.

I don't trust anybody.

That's anxious to help me.

What do you want?

What do you need?

It's not all molestation now, it's it's more industry angling.

What's your angle?

What are you trying to do.

It's like when women are nice to me and then like two days in they go, hey, is Trevor Noahs single?

I'm like, ah, you motherfucker.

I knew that's what it was.

So the reason why I told that story in the book is that.

Can give us the story, give our listeners a little version or the abridged version of that story.

I worked at a hospital in the cafeteria and my supervisor used to give me rides home from work if my car was broken down that week.

At a supervisor who did not live on my side of town, there were coworkers who lived on that side of town who would take me.

And my supervisor would go, no, I'm taking Roy.

Y'all go ahead and go home.

I'm taking Roy home.

And we would ride home and he would ask me a million questions about my life and what you're doing, and talk about girls.

I'm sixteen.

For context, this it's like a thirty thirty five year old man and what you're doing, what you're up to take you to the gas station, get your candy, to the point where after a while my favorite candies were already in the car, and I'm just I'm thinking that's odd, but I'm like, oh, this is my this is cool.

Also, I'm sixteen.

At that point, I think I'm out of the molestation window, because they make you believe that, Like for all the back to school specials and all the stuff they talk about with child kidnap and all of that, they made it seem like middle school was the cutoff for attractiveness the pedophiles and perverts.

And so my guard was down.

It was very much down.

And so one day he gives me a ride home and he goes, hey, I need to stop at a friend's house real quick.

You know, I gotta get ready.

I'm going to this thing to night.

I'm go, okay, cool, I'm waiting in the car.

It's a pretty rough neighborhood.

And he goes, you shouldn't wait in the car.

You know, GDS out here, Gangster Disciples, they out here, the GDS or get you whatever, Come on in the house.

I get in the house, I sit on the couch.

Ten minutes later, the cook from the hospital, he walks into the living room.

He's naked.

He's got a towel on, but he's to me, you're naked, You got on none but a towel.

You naked.

You shouldn't be in another room with another man, like your dick should never be flapping.

It's what my uncle Derek told me.

It's like, if your dick's flapping, you don't have enough clothes, go back, put some drawers on.

And he comes in and he sits on the couch and starts making small talk with me, and then my supervisor he comes out from the back.

This is called a power dynamic, everybody, this is a power dynamic from the hospital cafeteria.

He's in nothing but a towel, freshly showered, both of them, still got well, ain't even dried off.

Up top, two shirtless men in bath towel sitting next to me, and they start trying to make chit chat.

And that's when it clicked, and took it took a while, but that's when it clicked.

And I'm like, hey, my mom is waiting for me, and she's going to be looking for me.

And that was the one thing.

But that was the one thing I remember that somebody had taught me at the boy club was that if somebody's harassing you you feel like you're gonna get kidnapped, let them know that, you know, somebody going to the search will begin shortly after you snatch me.

Like, I don't know what y'all trying to do, but whatever it is, we're not gonna do that shit today.

Bro.

My mama waiting on me, and you can see them kind of both looking at you, and they're like asking me, like very like non hospital questions about you know, do you when the last time you had sex?

Do you like blow jobs?

Do the girls give you blowjob?

Like?

It was just very very on the nose, y'all trying to y'all trying to do some shit.

And I say, we gotta get the fuck up out of here, man, and and they agreed, and they got dressed, and they took me home, and my supervisor never talked to me again at work, no more rides home either.

Yeah.

I would think that confirmed, you know, in case you're mistaken.

Yeah, it's confirmed.

When they came out in bathtowels.

I mean, but you compare that to a manager I had.

I had a manager at Baskin Robbins hate it taking me home made it known that he didn't want to but would, but hated it.

We're still cool to this day, are you.

Yeah, because that's honesty, true benevolence.

I don't think real benevolence comes with excitement.

People would rather be doing something else, but they do it for you out of some love or respect or whatever, but or out of.

Some moral ups to do the right thing.

Ye yeah, or they just trying to fuck on the.

Couch right right.

Another similarity we have you and I is I had a big bomb at the Montreal Comedy Festival when I write before I got very successful, and you talk about being booed out of the Apollo and this.

Was supposed to be your life changing moment, and.

So what I want to talk I want you to talk a little bit about when your life changing moment doesn't become the moment that you wanted.

It to be.

How did you stay at the festival after you got booed?

It was so I didn't get booed.

I bombed, but I known booby But I mean it was a loud enough for me to understand that I bombed, And then I had a show the next night, and then I left and I remember being on the plane seeing all of these executives who were there to see me, and ah, it's sickening.

It was sickening.

I was so mortified at my own existence.

I went, It's one of those things where as soon as I walked on stage, I knew I picked the wrong jokes.

I had a joke that could have won me that round, and I saved it, thinking well, when I get to round two, that's when I'm gonna really hit them with the good jokes wrong.

And I had already had in my head like how it was going to play out, because Apollo, this is my first ever TV gig, this is O two.

I know if I do well here and I come back next week, I can get like literally, this sounds stupid, but my goal was to get in an ice Cube movie.

That was the It was the ice Cube to like Hollywood start them Pipeline.

Because Chris Tucker did well on Deaf Jam ice Cube song put him in movies.

Mike Epps did well ice Cube, soam put him in movies.

Kat Williams, Don d c.

Curry some more.

Like there's so many black comics that ice Cube was just like yeah, you you're famous now.

And I was like, this is gonna be my moment.

And I went out there and I ate shit.

Not only did I eat shit.

I was supposed to do three minutes.

I came off stage at two fifteen.

Two minutes fourteen fifteen, so I had one more joke left.

I go, they're not gonna let me do it.

I know they're not gonna let me finish the next joke.

I should leave now so that I don't get booed, and I said, good night.

I walk off stage.

But here's the joke on me.

You walked off stage.

That means you got to go back out and get Kiki Shepherd it where she you know, they put the hand over your head to judge and like, give it up for the first comedian, Yeah, give it up for Roy but Jr.

And the boo was louder than what would have been if I'd have just taken the original boo.

And the ride back to the hotel that night was just like so fucking like, it's it's everything.

You know, you're on a high and then immediately you're at your low as low and it's gone.

Now rip to the forty second Street McDonald's and Times Square, but I went there and had a big macmeal, I see orange to lick the wounds, and just sat there.

It was one of those nights where you're sitting there sad, and then you can see your reflection in the window and you're just like all this happiness streaking by and you're sitting there.

It's just I don't know what's next.

This was the way out and there's nothing I can do now to change this.

And I get back to the hotel we were staying.

I was bunking with another guy, Henry Coleman, great comic out of Memphis, and Henry and I were sharing a hotel room and Henry don Apollo same day got booed.

And we get back to the hotel we're staying at the Night's End in Elizabeth, New Jersey, and it's all open air prostitution and drugs, like the whole street.

Like, I don't know what it is now.

I know that Night's In is still there, number one, but I don't know what it is.

I don't know what that neighborhood is now.

We get back and the sex workers and the pimps and the dope boys that are out there.

They give us a round of applause, and it was one of the most meaningful moments of just it's like community upliftment because they knew we were there in town to do kind like we've been there a couple of days, and we talked a little bit in the parking lot.

They didn't know before we get out the car.

They didn't know whether or not we got booed or not.

They didn't know shit.

And it was like, to this day, I'm still touching.

Almost paid for some sex that night out of respect?

Have you ever paid for sex?

Roy?

Not outright, but right in theory all men have like not like give me a Venmo, thanks a lot, not like that.

Let's talk about walking away from jobs, another element that you and I have in common.

What was your final decision in walking away from the like quitting the Daily Show?

Did you have the CNN opportunity for your show on CNN, which is called Have I Got News for You?

No, you didn't have that job lined up.

No, that wasn't even rumored yet.

I left Daily Show October twenty two.

The CNN conversation happened that following July.

But I don't get the CNN opportunity if I don't quit Daily Show.

It just didn't feel like a place anymore where there was a solid plan for who the next host would be.

And then and I talked about it a little bit in the book about Also, I don't know, I just had ideas, Chelseay, I just had other shit I wanted to do that I know I couldn't do there.

I tried to do some of it there, it never got green.

Look like, I don't want to sound like somebody from SNL whining because I didn't get enough sketches on.

I got to do a ton of stuff.

But you start evolving and changing.

I'm like, well, Also, there was the paranoid of the merger.

I was, look, I don't know how you felt at the time, with all the guests hosting and your name being in the hat.

I was hyper paranoid about the merger.

Way depending paramount sky Dance, which finally happened.

Now that was cooking back then.

No I know, But why why did that worry you?

Because the first thing you do is cut You cut salary, you cut weight, when you merge a company, you cut things.

So whatever it is that's happened to Colbert.

If we really want to believe it was solely budget I thought that to be the Daily Show's fate with no host.

Well, it's the same people, right, right, right right, the same people run Colbert did run the Daily Show.

Okay, so now you're coming off of the writer strike, you you're a call from Comedy Central and they go, what's up?

You're coming back to work or not?

And then I go, y'all got a host?

They go, no, y'all got a plan for how you're gonna find a host?

Nope?

Well I know right there, I'm not on your short list.

Number two.

I know that if I stay, I don't know what I'm agreeing to stay to be a part of.

And I don't know how bulletproof this new configuration of the show will be.

Well, this be recession proof and merger proof.

John Stewart was also not in the cards at the time when I left the show.

That's an important detail because if John's coming back, all right, I stay another year and ride it out through the presidential election.

But if John's not, and if we're gonna cut costs, because even if you merge, right, let's just say they cut the Daily Show to a week.

Hey, we don't need to do this every night, Let's do it weekly.

Well, if you're gonna do it every week, I bet you don't need all these correspondents.

And if you're gonna cut correspondents, I bet you cut from the top, from the highest salary, longest tenure people.

This is just where my doom'sday brain is going at the time.

Right So they're gonna keep guest hosting.

The merger's gonna happen.

They're gonna trim fat.

I might be some of the fat they trim, and by the time they decide that they don't want me, or I decide I don't want to be here anymore, it's gonna be after the presidential election and the window of opportunity to do anything new in late night political satire will be gone.

This is the window right now, This is the window if you ever want to do anything different?

Are you willing to Are you willing to stay here for another year?

And bet?

Not having anywhere else to go, not knowing how the merger is gonna go, not knowing how the Daily Show it's going to be handled in the merger, or do you leave right now and figure it out the same as you always have.

Same as when the sitcom got canceled on TBS, same as when you got fired from the radio station.

Same as when you had the Whoopie the Whoopi Goldberg sitcom on lock and then it didn't happen.

So go back out into what you know, which is the unknown.

It's the most familiar feeling I have is not knowing what the hell is next.

Like everybody looked at it as some sort of courageous choice, but it's just like, no, if there's a new show to be made, it'll happen this year.

I want to be in line for another show.

Prescient, very prescient.

Yes, a lot of people call into this podcast Roy talking about this very thing.

I mean, you know, in different mediums and careers and professions, but when to take a jump or a leap of faith and having you know, not having the confidence to do that, and you talking about it and knowing that you're going to be okay, you know, because you've always been okay because of your work ethic and because of your hustle.

Like I think that's very powerful for people to hear and to know that, Like, you know, when you say no to something, you're saying yes to a whole bunch of other opportunities that may not have revealed themselves yet.

Trust yourself because they won't reveal themselves.

Ceing inn.

I wouldn't have if I was under contract with Daily Show for another year.

The CNN wouldn't even call because Central.

There's no way they're going to let me out of my deal to go do another show and essentially compete against them during the presidential election year.

Not gonna happen, bro, So they were never going to do that.

And then true true to form, there were two things that happened after that.

There were only two shows that came out that year.

It was The CNN Show and After Midnight with Taylor Tomlinson.

Those were the only two, and both of those shows are old ip that are remakes.

So it was even skinnier than I thought it was because I thought there was still room for a new show or a new idea.

There was not.

So, you know, I'm not going to say I lucked out, but I definitely had to leave to put myself in a position to advance and do anything else different, you know, and that it worked out, you know, But it just my advice to your listeners would be whatever emotion or fear you have, you've felt it before.

I think the gift is that you learn how to deal with that pressure or that fear and manage it in a way that makes sense.

Okay, if I leave this show and nothing else happens, what can I do?

Okay?

Oh, I never got around to writing that book.

I should write that book about all the dad shit.

Okay, I do that, and I can sell that script.

Maybe I could sell the script.

Yeah, I mean, you quit the Daily Show, You'll be hot for at least two months.

That's you know that.

I mean that's literally how my brain is processing everything at the time.

So I'm just like, there's other ways, and I think something else will present itself if I'm focused.

It's like the space shuttle where you keep coming around to Earth.

You got two windows of re entry.

You missed this re entry.

You gotta circle all the way back around and run out again.

Like no, I'll just I'll jump now.

At least this way, I have control over when I jump and I'm not pushed.

Yeah, right, exactly.

I love that We're going to take a break and we'll be right back with roy Wood Junior.

And We're back with roy Wood Junior.

We we'll start with a collar to Our first caller is Danielle.

She says, Dear Chelsea, I'm an actor, comic, and now an associate marriage and family therapist, and I love your advice.

I started stand Up in twenty twelve.

I've quit a couple of times over the years, but every time I leave, I can't stop thinking about it, and.

I always come back.

I restarted again in twenty twenty three, and this time I'm determined not to quit.

Right now, I'm hosting a weekly mic at Westside Comedy and I love it.

I'm forty two, with an MFA and acting from USC.

Over the years, I've booked some great roles, and I just finished filming a recurring role on a Netflix show coming out in twenty twenty six.

An agent once told me, you're over forty and haven't been a series regular, so your only hope is stand Up.

But clearly that hasn't been entirely true.

At the same time, I'm now building a career as a therapist.

After earning my MA in clinical psychology, I graduated and finished a year long internship in June.

Here's my struggle.

I constantly compare myself to younger comics who seem miles ahead.

The voice in my head says, why bother?

You'll never get on late night, you'll never get your name on the wall at the comedy store, and you'll never be a real comic.

I bomb Hard hosting four casino shows recently, which left me wondering.

Do I grind away and write material for any crowd or should I focus on shaping comedy that really reflects who I am?

Psychology based material?

Should I be aimed at therapists, mental health professionals and maybe try to get gigs at mental health conferences?

No?

How do I keep moving forward without abandoning myself to comparison or self doubt?

Danielle Well?

First of all, Hi Danielle, how are you?

Hi?

I'm so good, Thank you for having me.

This is our special guest, Roy Wood Junior.

Two comedians that you could talk to right now.

Hi, daniel One time for the West Side with the good Mexican food upstairs.

Right on.

First of all, don't gear your casinos suck?

Okay, just so you know, I'm saying, I mean, you know, because most casinos suck.

I have a residency at a casino that does not suck, but a lot of casinos do suck.

Especially you know that's not your target crowd, so don't let that.

That's part of the process.

Also, bombing is part of the process.

It doesn't feel good when it's happening, obviously, but it makes you a stronger comic.

Roy would you agree.

With that, absolutely, it's the repetition of it all.

Also, you're still stuck on you at twenty twelve, so you're measuring yourself in progress from twenty twelve.

I feel like if you start comedy and stop, you essentially start back at zero again whenever you come back in, because you're a different person.

You can't even do those old jokes anymore.

You can't compare yourself to the young And it's a leap frog game.

Some start late, some start early, Some leapfrog and then fizzle out, some figure it out later.

I think that that part of it.

I think the name of the game.

The advantage you have over any actor is that you can build an audience.

And if you have an audience, then you have control, which means you can write your own thing, you can create your own thing, and you're a comic with the real world experience, like you didn't just do this forever, like you've had regular jobs and shit, you've had an experience.

I think that you lean into the material that will get you rebooked at you know, some of these club spots and stuff like that.

But if you can find your own audience online.

If it was ten years ago, I'd have told you be broad, pray for a Jimmy Fallon Late Night set, and then maybe that'll be the thing that gets you to the Montreal Showcase.

Now, if you become the person that has a sandbox that works exclusively in a thing, you can grow and build from that and have a very viable audience.

You know, when I think about like the guys We Fucked podcasts, or if you think about, say, I'm trying to think of like some of the other stand ups that just went off and did their own thing.

I'm just over here doing the part.

Mark Maron's a great example where it's just I'm just gonna talk about the things that matter to me, and the people who find me are the people who will cherish it honestly.

To pay bills and so you tell me if I'm right or wrong on this.

To pay bills.

Even in New York, you only need twenty cities where you can sell about four hundred tickets.

Maybe let's just let's say a thousand tickets.

If you do four nights, two fifty a show, you could pay bills just on twenty cities.

Now, will you be big?

Will you be huge?

Will you be everywhere?

I don't know that's debatable, but I really do think that the idea of success versus stardom is something that's blurred.

And I think that comedians who are on, who feel like they're on the outside looking in, look at stardom as the only form of success.

You can go do those corporate I bet you one of them therapy conferences will pay your ass twenty five K to one hundred k to Aventure.

I remember there was a guy I opened for.

I think his name is Mark Klein.

If I'm not mistaken, Mark Klein used to call himself the core corp, the corp gesture he only did corporates.

I don't think in my and I'm not saying it's to shit on Mark Klein if he's still out there doing stand up.

I don't think he had a television credit in the two thousands and was living comfortably and great.

So it's all about what your idea of success is as well, because if you could bring humor to the MFA world, there's not a lot of people qualified to even tackle into that, so you could be the beachhead.

Also, look at Leanne Morgan.

I mean, she just hit it.

She's older than everybody here.

You know, she just hit it the last few years.

So you don't know when you know your success or your version of success is going to happen.

But you know, comparing yourself to others is not uncommon.

Everybody is doing that because of social media.

But it's not a great habit.

It doesn't bring out the best in any of us to sit there and look at what other people are doing.

You have to be confident in the fact that you have your own path and that you're going to go down the road that you're going down, that the road that is curated for you by you, you know what I mean.

You're the one who's making decisions around yourself and around your career and what you're going to do, and you have to have confidence in that in and of itself, that's what you're doing something how many other people are doing what you're doing not, you know, probably not very many who have a degree an MFAA.

Do you have a marriage, Family, Child Counseling MFCC and your other Bachelor of Fine Arts?

Did you also say that you had one of those MFA from USC acting MFA.

Sorry, okay, so they're a Master of Fine Arts.

So that's already original.

You know, that's stuff you can use.

And I wouldn't curtail your material to different people.

It's like you kind of like, I feel this way.

I don't know, Roy, you tell me, I do my thing wherever I am, Like, I don't ever adjust it for people, because I just feel like you have to really know what you're doing on stage and be completely committed to that material because if you're or not, that's when you have a bad experience or a week set or you get or you feel like you bombed.

Is when you're not confident, you know, because you can.

Smell t to be something you weren't for an audience that was never going to appreciate the truest version of you.

So now you're just it's like, you know, if you think of comedy as a relationship and you on stage is the first date.

How much are you going to pretend to be something just so that that particular date likes you?

Well, then who the who the fuck are you?

It's a great analogy.

It's just likability and trying to get people to like you enough to go on a journey with you, and some people might not.

I do think one thing that, And I don't know what your writing habits are, but critique yourself often and try to find and squeeze an extra line of laugh out of material.

I'm not gonna like I write the tightest for laugh per minute type sets, but I think a lot of people, especially in New York, a lot of the newer comics, in my opinion, they get very comfortable once the joke gets a laugh or two and they go, Okay, that joke's done.

Like, no, it might not be.

Think of it.

Listen to it a couple of different ways, Like just you can message me offline and I can give you what my approach has always been.

It's just what happens if I tell this joke louder, faster, or a different octave.

You could take words that aren't even funny and make them funny.

Like there's ways to just juice another laugh out of stuff, and be comfortable with hating yourself, because sometimes I listen to audio of myself and I watch it as a hater, like listen to it as he and then I give tags like well what he should have said was this?

Oh, well i'm him.

Well I just tag my own shit just by listening to it.

It's a free joke, so you know that part of it.

Don't run away from it.

But I really do think that the idea of just performing and waiting for you know, comedy Jesus to find us in the back of the comedy clubs, I think those days are gone.

I think it's all about being yourself consistently enough and then growing from there.

I stop short of telling comedians to put clips out every week or every month or whatever, but find a pace that makes sense for you, or be the comic that's responsive to a particular issue on a regular basis.

And maybe that's your thing, or maybe it's the Hey, this current event happened.

Let me show you how this fits into the world of therapy.

Yeah, here's too.

You know that's interesting.

I'm mentioning on like world events, pop culture, whatever, you're the most passionate about through the lens of with that.

Bet Well, I think mental health and therapy stuff like does play more broadly nowadays, Like we all have that language.

It's become Dear Weger, I also want to say that Corpjester dot com is alive and well, so Mark Klein is out there, danns Wow.

Awesome.

Okay, Well, I hope that was helpful.

Danielle very I really appreciate it.

Thank you so much for the time.

Sure, nice to meet you both.

Nice to meet you, Danielle.

Nice to see you, Catherine.

Thank you.

Guys.

We're going to take a quick break and we'll be right back with roy Wood.

And we're back with roy Wood Junior and Senior.

Okay, so our last question comes from Carrie.

This one was just an email, she says, Dear Chelsea, I'm not a stand up comedian, comedian or frontline act i E.

Entertainer.

However, I'm in the entertainment business and understand how it all works.

I'm heavily involved in the music SNL thirty rock comedy scene on the business end.

Years ago, I pursued a guy who's involved with a comedy podcasting and he didn't show reciprocated feelings.

Now, two years later, I'm really interested in another comedian, but I'm scared to be labeled as a chuckle fucker.

I feel like only women get these labels, and I'm not sure how to navigate it.

Do I just say fuck it and shoot my shot?

Or should I look elsewhere?

Carrie?

Yeah, fuck it?

What do you care what?

It's a chuckle fucker anyway, I mean, who gives a shit what anyone thinks.

If you like funny men, you like funny men.

Also, chuckle fucker's reserved for people not in the business.

And this is as a guy who's fucked a couple chuckle fuckers.

Chuckle Fuckers are not people that are within the industry.

You're just somebody in the industry dating people in the industry.

Cops fuck cops, sometimes they fuck firefighters.

I think you shoot your shot.

I do think that I would be very discreet about it.

I wouldn't put a lot of public appearance on that.

Just know that if it's taking off at some point, he's gonna tell a friend or a buddy or whatever.

But you know, why not fill it out and just say hello, oh, just you know.

Yeah, exactly.

I wouldn't worry about your label being labeled anything you're in.

You know you're in the business.

You're in the business.

Just because you're not a comedian doesn't mean you're not.

In the business.

It's all related and who cares.

My god, we're all gonna die soon anyway, it doesn't fucking matter.

Yeah, I don't know how old that person is, but once they get into the thirties, you're going to realize that there's a couple of comics that have all cross pollinated and you know, never openly dated one not is it like a title of girlfriend, but I've dated like two or three comedians.

Well, I think you and Yaminika should start dating.

That's my start.

Rumors stn't start.

You know, she's looking for someone, she's looking for someone to land on, and it might just be you.

It might just be you, and I've told her a long time ago.

I don't know if you step mo material I got a nine year old, you might try and cuss out my baby and then his mam would be over.

Let me stop.

Talking before we let you go.

I just want to know, since you have a political show and you're a political commentator, Well, how do you see what's your view or long lens of our current political situation.

How do you see things?

I think that we are into an administration that, if we are not careful, is going to be controlling the messaging through all of the media, through lawsuits and intimidations and leveraging money as a way to silence voices.

And I don't think that's something that's exclusive to liberals.

If you want to get you know, get into the weeds of freedom of speech and stuff like that.

Like that part, you know, scares me for sure, Like that's real cancel culture when you can't even vocalize or verbalize anything, or someone controls all the airways so you can't even get equal time to spit your opinions and perspectives.

That makes me nervous.

But it was nice to see what I perceived to be the comedy community together on the Jimmy Kimmel joint and all saying well, wait, you can't do that.

And that gives me hope because comedians are still the tip of the spear.

If anything's going to change, I think it starts with comedians and also strippers, because the strippers be dancing for the politicians and.

Thank you very much for that sentiment.

Thank you, Roy Wood Junior.

You can catch him on CNN.

His show is called Have I Got News for You?

His new book is called The Man of Many Fathers.

It's an incredible book.

I recommend every mother getting this and reading it, and any straight men that are listening to this you should.

Read it too.

But I doubt there are a lot of straight men listening to this podcast, and women read more than men, So there we go.

I'm glad to be a woman.

I'm proud of our female listener readers, and who needs straight men anyway?

Thank you Roy Wait for a minute now.

Congratulations, right, We love you, Thank you for coming on.

The word of the week is penurious, adjective given to or marked by extreme frugality.

Penurious, the penurious miser declined to put a coin in the Salvation army bucket.

Penurious.

I just announced all my tour dates.

It's called the High and Mighty Tour.

I will be touring.

From February through June, So go get your tickets now if you want good seats and you want to come see me perform, I will be on the High and Mighty Tour.

Do you want advice?

From Chelsea right into Dear Chelsea Podcast at gmail dot com.

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Dear Chelsea is edited and engineered by Brad Dickert executive producer Catherine Law and be sure to check out our merch at Chelsea ham Dour dot com m