Dear Chelsea - Trifling White Women with Roy Wood Jr.
Episode Date: November 27, 2025The Daily Show’s Roy Wood Jr. joins Chelsea to talk about the life lessons he learned from unexpected people, why nobody wants to do you a favor unless they have an ulterior motive, and debate w...hether his parents had an open marriage way before it was cool. Then: A 40+ standup wonders where to focus her time. And a comedy-adjacent New Yorker tries not to become a Chuckle F*cker. * Pick up a copy of The Man of Many Fathers here * Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees. This Podcast should not be used as medical advice, mental health advice, mental health counseling or therapy, or as imparting any health care recommendations at all. Individuals are advised to seek independent medical, counseling advice and/or therapy from a competent health care professional with respect to any medical condition, mental health issues, health inquiry or matter, including matters discussed on this Podcast. Guests and listeners should not rely on matters discussed in the Podcast and shall not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice. See omnystudio.com/listener for privacy information.
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But our guest today had a great bug.
I really loved it.
You know our guest today from The Daily Show and CNN's 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 Jr. 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.
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, not of them 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?
Correct.
They're great.
So, but you talk in the book, we're going to jump around a little bit because in the book,
because 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 my pop stepped out, it was with her.
And so for my mom, I think it was,
I know what's happening, but I'm going to keep my head down.
The money I'm saving on rent,
I'm pouring into law school,
and then I'm going to fucking leave you.
In the meantime, these women are not going to 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 60s.
She was the first wave of students
to integrate Delta State University.
It's a university that, as of recent, is in the news
because of two black people being found hung.
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 going to be scared of some random woman coming to the house
trying to cuss my daddy out.
You're going to get, you're going to get slapped up.
Well, she's going to come back with a bat is what happens in the book.
Yeah, my bat.
I couldn't even use it anymore literally after that because the glass.
That's a separate conversation.
Well, yeah, she, 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 going to tell me everybody that is married is successful and truly happy.
So don't throw these 30-year, 40-year relationships in my face as an example of what could be.
you know, 40 years, how many happy?
Mm-hmm.
And that's the question married 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 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 off one or one that's not cooperative,
that's fucking stressful.
I can't really unload them 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.
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.
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 submit.
Like, he's just a journalist who focused solely on struggling conflict on issues affecting
black people globally.
And when you spent 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
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 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 Burmonds
Birmingham City Schools are still in session, so rather than get a babysitter, he just dropped me off it. And 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 putt put or have a fun, cool father's, it's literally, hey man,
Jesse Jackson's in town for the Democratic National Convention.
I'm going to 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 peneurious,
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.
Because 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 40 minutes before I got to the liquor store and I still had about a night.
another hour to go to get home.
And what was the temperature?
It was about 15 degrees, maybe 20.
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 in 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, you're like, you're talking those in that era in the
90s. Don't take a ride from a stranger. And I'm like, fuck it, bro. Even if you're going to 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 drinking drive while he took me home. I know. That was a very nice
touch to that story.
You think it's almost a misdirect.
You think he is going to molest you.
And instead he's like, you know what?
I'll save my drink until after 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 15-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 convinced
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 are y'all not noticed that I'm not here yet? Yeah, 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, 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's snapping on her about something. You tell a story about being a kid
and getting an argument with your mom over a toy that you wanted at the mall. 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 going to leave you
in the mall.
And my mom walked off and 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 gallery 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 joyce come over here and this fucking white cashier chelsea pulls up the pa system in macy
and hands it to me.
And then I'm just on the mic,
Mama, where are you?
I'm in women's stockings.
This Roy, click.
And my mom comes over furious, cusses out the white lady.
My mom is a 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.
Because in my mom's mind,
it's they're going to take you from me.
Yeah, right.
That's all her thought were is that you called the police.
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's really the most really weird white women.
There was a semi-racist incident in Tallahassee with a partner of mine.
But, like, is it racism if they're right?
What's, which, a partner of yours, what do you mean a partner of yours?
Let me 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 17 years old, maybe 18, 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 sales rep comes over she goes we don't have layaway we haven't said shit she hasn't said
hello how you're doing shit can i help you my name is eva whatever and we go we don't need lay
away and we snap back at her real fast and she walks off and then we looked at the price of them
jackets and fucking we needed layaway them shits was like it's a leather jacket that shit's like
starts at a thousand dollars we thought this would be a hundred and fifty dollar
like fucking starter jacket,
like some NBA Jordan chalk line.
It was $1,000.
So me and Barrett spend the next 30 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.
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 is 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, ah, 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.
My dad never brought me around his side of the family.
Only like family reunions and I know my half, I don't 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.
Well, he disappeared in the night without a trace in Georgia in the 1930s.
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 16
and crippled permanently while running after a woman
that had just broken up, a girl,
because he was 16, 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,
My pops was pretty much fucked from age four, and we was solidified at age 16.
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 in women, I guess, but you comfort yourself into people, you know, that praise 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 16. And then you start hearing all these cool stories and great
stories about him. And I didn't get that. I never saw or experienced that. One of the
hardest things for me to do is I follow my two younger siblings. I'm closest to them because
we're closest in age. And with me and the older halves, it's a 20 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 in 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 flat
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
Dukakis in 84
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
and the other woman.
I have to.
And I have to unpack that.
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 eye-opening.
Because, I mean, you know my stand-up.
I don't talk about my life.
I don't talk about it because it was just so weird.
It was so complicated.
It was easier for me to just talk about it.
about the world. But, you know, I look at, 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 10 years of his
life. So you go around, I'm the ninth of 11 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're, you're
you love, but also running from this commitment and irresponsibly 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.
No, I have one child that I co-parent with his mom,
and that's great.
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 falls second.
So when there are huge responsibilities and big things that I have to take care of,
I might, I don't run, is not the right word,
but I'll anxious avoid 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 coming.
Yeah, your dad, in 1971, got me in my first.
And I remember I needed a tape recorder,
and we was at the press gun.
Your daddy loaned me his audio.
And like, it's just these, he loved what he did.
Also, I think to a degree, just ran from everything else.
So, you know, you have to unpack who your parents are 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.
I guess what I bought about a mother.
month ago, I bought that same black Voltron lion that I was crying to my mom about in Memphis
in the 80s. And I saw it at like a collectible store. I was like, yeah, I'm going to get that
fucking lion now. I don't have it on one of these days. 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
much baseball all day. But I do feel like there's a degree of joy and fun that I lost because I had
to work. 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, no electricity. You know, my mom was working
her ass off two jobs in night school and law school and grad school. I don't want to bother her.
with needing $50 for the sneakers or the field trip.
So I'm going to hustle.
So, yeah, I missed out on a lot of things.
Yeah.
I missed out.
I missed out on a lot of things 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.
Now, what we were doing, oh, they would have taken me away.
from my mom in a heartbeat.
First of all, let's talk about your almost threesome that you had,
getting a ride 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, we're like, here's the thing.
They tell kids, hey, be careful.
Don't let nobody touch you in your area, right?
Right.
Like, make sure no one touches your breasts.
they never tell you how perverts spit game.
Is that a better way of putting it?
Yeah, like the grooming.
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 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 Noah 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 you need to see.
Can you 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,
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 16 for context. It's like a 30, 35 year old man.
And what you're doing, what you're up to, take you to the gas station.
get you 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 boss this is cool also I'm 16 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 got to get ready.
I'm going to this thing tonight.
I'll 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, G.D.'s out here.
Gangster disciples.
They out here, the GDs will get you, whatever.
Come on in the house.
I get in the house
I sit on the couch
10 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 nothing but a towel
you're 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 on 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 towels sitting next to me
and they start trying to make chit-chat.
and that's when it clicked and it 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 remembered that somebody taught me at the
boys club was that if somebody's harassing you and you feel like you're going to 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 going to do that shit today bro
my mom are waiting on me and you can see them kind of both look at each 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 blow jobs like it was just very very on the nose
y'all trying to, y'all trying to do some shit.
And I was like, we got to fuck up out of here, man.
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 those.
Which confirmed, you know, like.
In case you're mistaken.
I think that was confirmed when they came out in bath towels.
I mean, but you compare that to a manager I had, I had a manager at Baskin-Robbins.
hated 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 compass to do the right thing.
Yeah.
Or are they just trying to.
the 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, right 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 want it to be. How did you, did you stay at the festival after you got booed?
It was so, I didn't get booed.
I bombed, but no one booed me, but I mean, it was allowed 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, uh, is 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 going to really hit them with the good jokes wrong.
And I'd already had in my head, like, how it was going to play out.
Because Apollo, this is my first ever TV gig.
This is O2.
I know if I do well here, and I come back next week, I can get like,
and literally this sounds stupid, but my goal was to get an,
an Ice Cube movie.
That was the, it was the Ice Cube to, like Hollywood Stardom Pipeline because Chris Tucker
did well on Def Jam, Ice Cube saw him, put him in movies.
Mike Epps did well, Ice Cube saw him, put him in movies.
Kat Williams, Don D.C. Curry, some more.
There's so many black comics that Ice Cube was just like, yeah, you, you're famous now.
And I was like, this is going to 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 2.15, 2 minutes, 14, 15.
I had one more joke left.
I go, they're not going to let me do it.
I know they're not going to 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 Shepherded.
where she, you know, they put the hand over your head to judge.
And like, give it up for the first committee.
Yeah.
Give it up for Roy Wood Jr.
And the boo was louder than what would have been if I had just taken the original boo.
And the ride back to the hotel that night was just like so fucking, like, like, it's everything, you know, you're on a high.
And then immediately you're at your lowest low.
And it's gone now RIP to the 42nd Street, McDonald's, and Times Square.
But I went there and had a Big Macmill, High Seat 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 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 I was bunking with another guy Henry Coleman great comic out of
Memphis and Henry and I were sharing a hotel room and Henry at 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 like community upliftment.
because they knew we were there in town to do kind of like we've been there a couple 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 touched like i almost paid for some sex at 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 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 of 22 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 talk about it a little bit in the book about also, I don't know,
I just had ideas, Chelsea. 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.
I don't want to sound like somebody from S&L 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 paranoia 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.
In what way?
the pending Paramount Skydance, which finally happened now,
that was cooking back then.
No, I know, but why was, 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 did run Colbert, did, yeah, run the Daily Show.
Okay, so now, you're coming off of the writer's strike.
You get 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, nope, y'all got a plan for how you going to 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.
Will 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 going to 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 going to do it every week, I bet you don't need all these
correspondence.
And if you're going to cut correspondence, I bet you cut from the top, from the highest salary
long as 10 year people.
This is just where my doomsday brain is going at the time, right?
So they're going to keep guest hosting.
The merger's going to happen.
They're going to 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 going to 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 stay here for another year
and bet not having anywhere else to go, not knowing how the merger's going to go,
not knowing how the daily show is 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 Whoopi,
the Whoopi Goldberg sitcom unlock 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.
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.
Preciant.
Very prescient.
So I quit.
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.
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.
CNN, I wouldn't have, if I was under contract with Daily Show for another year,
the CNN wouldn't have even called because Comedy 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 going to 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 end show and after midnight with uh 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 the writing that book.
I should write that book about all the dad shit.
Okay, I do that.
I can sell that script.
Maybe I could sell a script.
Yeah, I mean, you quit the daily show.
You'll be hot for at least two months.
That's, you know, 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 the earth
You got two windows of reentry
You miss this reentry
You got a 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 Jr.
A decade ago, I was on the trail of one of the country's most elusive serial killers,
but it wasn't until 2023 when he was finally caught.
The answers were there, hidden in plain sight.
So why did it take so long to catch him?
I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer,
the investigation into the most notorious killer in New York,
since the son of Sam, available now.
Listen for free on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts.
Hi, I'm Dr. Priyank Wally.
And I'm Hurricane DeBolu.
On our new podcast Health Stuff, we demystify your burning health questions.
You'll hear us being completely honest about our own health.
I'm talking about very serious stuff right now, and you're laughing at me.
And you'll hear candid advice and personal stories from experts who want to make health care more human.
Sometimes you're there to listen, to understand, to empathize, maybe to give them an understanding or a name for what's going on.
That helps people a lot, understanding that it's not just in their head.
We are breaking down the science, talking with experts, and sharing practical health tips you can
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We human beings, all we want is connection.
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We want to make health less confusing and may be.
Maybe even a little fun.
Find held stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
I'm Robert Smith.
This is Jacob Goldstein.
And we used to host a show called Planet Money.
And now we're back making this new podcast called Business History about the best ideas and people and businesses in history.
And some of the worst people, horrible ideas and destructive companies in the history of business.
Having a genius idea without a need for it is.
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want. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the
airline business. The most Texas story ever. There's a lot of mavericks in that story. We're going to
have mavericks on the show. We're going to have plenty of robber barons. So many robber barons.
And you know what? They're not all bad. And we'll talk about some of the classic great moments of
famous business geniuses, along with some of the darker moments that often get overlooked. Like Thomas Edison
and the electric chair.
Listen to business history on the IHeart radio app,
Apple Podcasts, or wherever you get your podcast.
Hey there, Dr. Jesse Mills here.
I'm the director of the men's clinic at UCLA Health.
And I want to tell you about my new podcast called The Mailroom.
And I'm Jordan, the show's producer.
And like a lot of guys, I haven't been to the doctor in many years.
I'll be asking the questions we probably should be asking, but aren't.
Because guys usually don't go to the doctor unless a piece of their faces.
is hanging off or they've broken a bone.
Depends which bone.
Well, that's true.
Every week, we're breaking down the unique world of men's health,
from testosterone and fitness to diets and fertility,
and things that happen in the bedroom.
You mean sleep?
Yeah, something like that, Jordan.
We'll talk science without the jargon
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It's going to be fun, whether you're 27, 97, or somewhere in between.
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We don't just want you to live longer.
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So check out the mailroom on the IHeart Radio app,
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I'm Wilmer Valderrama, and yes, I grew up watching
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But for me, I saw myself in his story.
From plening canary cages to this night here in New York, it's a long ways.
On the podcast starring Desi Arnaz and Wilmer Valderama,
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The moments it has overlapped with mine,
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how we carry his legacy today.
Listen to starring Desi Arnaz and Wilmer Valderrama.
As part of the My Cultura podcast network available on the IHartRadio app, Apple Podcasts, or wherever you get your podcast.
And we're back with Roy Wood Jr.
Well, we'll start with a caller today.
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 2012.
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 2023, and this time I'm determined not to quit.
Right now, I'm hosting a weekly mic at West Side Comedy, and I love it.
I'm 42 with an MFA in 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 2026.
An agent once told me, you're over 40 and haven't been a series regular, so your only hope
a 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 bombed 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 abandon myself to comparison or a 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, Jr.
Two comedians that you could talk to right now.
Hi.
Hello, Danielle.
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 there
2012, so you're measuring yourself in progress from 2012. 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 ones.
It's a leapfrog game. Some start late. Some start early. Some leapfrog and then physical.
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 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'll get you
rebooked at some of these club spots
and stuff like that. But if you can find your own
audience online, if it was
10 years ago, I'd have told you to 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.
But 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 a pot
Mark Maron's a great example where it's just
I'm just going to talk about the things that matter to me
and the people who find me or the people who will cherish it
honestly to pay bills
and Chelsea you tell me if I'm right or wrong on this
to pay bills
even in New York
you only need 20 cities where you can sell about 400 tickets maybe let's just say a thousand tickets
if you do four nights 250 a show you could pay bills just on 20 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 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 25K to 100K to adventure. 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 C-O-R-P,
the corp jester. He only did corporates.
I don't think in my, and I'm not saying this 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 2000s 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 them to 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 is the road that is curated for you, by you.
You know what I mean?
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, 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 and MFAA or, do you have a marriage, family, child counseling, MFCC?
And your other, and a Bachelor of Fine Arts, did you also say that you had one of those?
MFA from USC, yeah, acting. MFA, sorry. Okay, so there, 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 not, that's when you have a bad experience or a weak set or you get
or you feel like you bombed is when you're not confident, you know, because that you can smell that.
You tried 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're on stage as 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 fuck are you?
It's a great analogy, yeah.
It's just likeability in 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 going to add like I write the tightest
four 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
way. Like, just, you can
message me offline and I can give you
what my approach has always been. It's
is what happens if I tell
this joke louder, faster, or
at 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, like, I listen to audio of
myself and I watch it as a hater.
Like, listen to it as a hate. And
then I give tags, they're like, well, what he should
have said was this. Oh, well, I'm him.
Well, I just tagged 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 stopped 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. Through the lens of therapy is a good idea too. You know,
commenting on like in world events, pop culture, whatever you're,
the most passionate about through the lens of therapy with that bent.
Well, and I think mental health and therapy stuff, like, does play more broadly nowadays.
Like, we all have that language.
It's become derroar.
I also want to say that corpgester.com is alive and well.
So Mark Klein is out there doing a thing.
Wow.
Look at him.
Shut up to Mark Cline.
Awesome.
Okay, well, I hope that was helpful, Danielle.
Very.
I really appreciate it.
Thank you so much for taking the time.
Sure.
Nice to meet you both.
Nice to meet you.
Danielle. Nice to see you, Catherine. Thank you.
We're going to take a quick break and we'll be right back with Roy Wood.
A decade ago, I was on the trail of one of the country's most elusive serial killers,
but it wasn't until 2023 when he was finally caught. The answers were there, hidden in plain sight.
So why did it take so long to catch him? I'm Josh Zeman, and this is Monster,
hunting the Long Island serial killer, the investigation into the most notorious killer in New York
since the son of Sam, available now.
Listen for free on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts.
Hi, I'm Dr. Priyank Wally.
And I'm Hurricane deBolu.
On our new podcast Health Stuff, we demystify your burning health questions.
You'll hear us being completely honest about her own health.
I'm talking about very serious stuff right now, and you're laughing at me.
And you'll hear candid advice and personal stories from experts who want to make health care
more human. Sometimes you're there to listen, to understand, to empathize, maybe to give them an
understanding or a name for what's going on. That helps people a lot, understanding that it's not just
in their head. We are breaking down the science, talking with experts, and sharing practical
health tips you can actually use in your day-to-day life. From when to utilize and avoid
artificial light to how to sleep better. Everything you need to know about fiber and how to poop better.
How to minimize the effects of jet lag and how to stay hopeful in time.
of distress. We human beings, all we want is connection. We just want to connect with each other.
We want to make health less confusing and maybe even a little fun. Find health stuff on the
IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith. This is
Jacob Goldstein. And we used to host a show called Planet Money. And now we're back making this new
podcast called Business History about the best ideas and people and businesses in history. And
some of the worst people, horrible ideas, and destructive companies in the history of business.
Having a genius idea without a need for it is nothing. It's like not having it at all.
It's a very simple, elegant lesson. Make something people want.
First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline business.
The most Texas story ever.
There's a lot of mavericks in that story. We're going to have mavericks on the show. We're going to have plenty of robber barons.
so many robber barons. And you know what? They're not all bad. And we'll talk about some of the
classic great moments of famous business geniuses, along with some of the darker moments that
often get overlooked. Like Thomas Edison and the electric chair. Listen to business history on the
iHeart radio app, Apple Podcasts, or wherever you get your podcast.
Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA Health. And I want
to tell you about my new podcast called The Mailroom. And I'm Jordan, the show's producer.
And like a lot of guys, I haven't been to the doctor in many years.
I'll be asking the questions we probably should be asking, but aren't.
Because guys usually don't go to the doctor unless a piece of their face is hanging off or they've broken a bone.
Depends which bone.
Well, that's true.
Every week, we're breaking down the unique world of men's health, from testosterone and fitness to diets and fertility and things that happen in the bedroom.
You mean sleep?
Yeah, something like that, Jordan.
We'll talk science without the jargon and get you really.
answers to the stuff you actually wonder about. It's going to be fun, whether you're 27, 97,
or somewhere in between. Men's Health is about more than six packs and supplements. It's about
energy, confidence, and connection. We don't just want you to live longer. We want you to live
better. So check out the mailroom on the Iheart radio app, Apple Podcasts, or wherever you get
your favorite shows. What do you get when you mix 1950s Hollywood, a Cuban musician with a dream,
and one of the most iconic sitcoms of all time.
You get Desi Arnaz, a trailblazer, a businessman, a husband,
and maybe most importantly, the first Latino to break prime time wide open.
I'm Wilmer Valderrama, and yes, I grew up watching him,
probably just like you and millions of others.
But for me, I saw myself in his story.
From plening canary cages to this night here in New York, it's a long ways.
On the podcast starring Desi Arnaz and Wilmer Valderrama,
I'll take you in a journey to Desi's life,
The moments it has overlapped with mine, how he redefined American television, and what that meant for all of us watching from the sidelines, waiting for a face like hours on screen.
This is the story of how one man's spotlight lit the path for so many others and how we carry his legacy today.
Listen to starring Desi Arnaz and Wilmer Valderrama.
That's part of the MyCultura podcast network available on the IHard Radio app, Apple Podcasts, or wherever you get your podcast.
And we're back with Roy Wood Jr. and senior.
Okay.
So our last question comes from Carrie.
This one's just an email.
She says, Dear Chelsea, I'm not a stand-up comedian or front-line 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 30 rock comedy scene on the business end.
Two years ago, I pursued a guy who's involved with the comedy podcast scene 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'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 fuckers reserve for people
not in the business, and this is 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 going to tell a friend or a buddy or whatever.
But, you know, why not fill it out and just say hello?
Just, you know.
Yeah, exactly.
I wouldn't worry about your label being.
labeled anything. 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
going to die soon anyway. Doesn't fucking matter. Yeah, I don't know how old that person is.
But once they get into the 30s, 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 as a like a title of girlfriend,
but I've dated like two or three comedians.
Well, I think you and Yamanika should start dating.
That's my...
Don't start rumors.
Don't start rumors.
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, Roy.
And I've told her a long time ago,
I don't know if you stepmom material.
I got a nine-year-old.
You might try and cuss out my baby.
And then his mama be over here to cuss your ass.
Let me stop talking.
Before we let you go, Roy, I just want to know, since you have a political show and you're a political commentator, what, 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 airwaves
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 perceive to be the comedy community coming 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, Jr.
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 a minute now.
Okay.
And on that no, congratulations, Roy.
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 panurius miser declined to put a coin in the Salvation Army bucket.
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?
Write into Dear Chelsea Podcast at gmail.com. Find full video episodes of Dear Chelsea on YouTube
by searching at Dear Chelsea pod.
is edited and engineered by Brad Dickert,
executive producer, Catherine Law.
And be sure to check out our merch at chelseahandler.com.
Hey there, Dr. Jesse Mills here.
I'm the director of the men's clinic at UCLA,
and I want to tell you about my new podcast called The Mailroom.
And I'm Jordan, the show's producer.
And like most guys, I haven't been to the doctor in way too long.
I'll be asking the questions we probably should be asking, but aren't.
Every week, we're breaking down the world of men's health from testosterone and fitness to diets and fertility.
We'll talk science without the jargon and get your real answers to the stuff you actually wonder about.
So check out the mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get, your favorite shows.
On this week's episode of Next Chapter, I, TD Jake, sit down with Denzel Washington, a two-time Academy Award-winning actor and cultural icon.
conversation about change, identity, and the moment everything shifted.
I mean, I don't take any credit for it.
It's nothing I did as special, you know, did knock down a few pegs and recognize it, but
I just didn't put me first.
I just put God first and he's carried me.
Whether you're rebuilding, reimagining, or just trying to hold it together, this one will
speak to you.
Listen to the next chapter podcast on the I Heart Radio app, Apple Podcasts, or wherever you
get your podcast, new episodes drop weekly.
Don't miss one of them.
Hi, I'm Dr. Priyanka Wally.
And I'm Hurricane DeBolu.
On our new podcast Health Stuff, we demystify your burning health questions.
You'll hear us being completely honest about our own health.
My residency colon was like a cry for help, honestly.
And you'll hear candid advice and personal stories from experts who want to make health care more human.
I feel like they never felt like I truly belonged in medicine.
We want to make health less confusing and maybe even a little fun.
Find health stuff on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.
The Big Take podcast from Bloomberg News keeps you on top of the biggest stories of the day.
My fellow Americans, this is Liberation Day.
Stories that move markets.
Chair Powell opened the door to this first interest rate cut.
Impact politics, change businesses.
This is a really stunning development for the AI world
and how you think about your bottom line.
Listen to the big take from Bloomberg News every weekday afternoon
on the IHeart radio app, Apple Podcasts, or wherever you get your podcasts.
I'm Robert Smith.
This is Jacob Goldstein.
And we used to host a show.
show called Planet Money. And now we're back making this new podcast called Business History
about the best ideas and people and businesses in history. And some of the worst people,
horrible ideas and destructive companies in the history of business. First episode,
how Southwest Airlines use cheap seats and free whiskey to fight its way into the airlines.
The most Texas story ever. Listen to Business History on the IHeart Radio app, Apple Podcasts,
or wherever you get your podcasts. This is an IHeart podcast.
Guaranteed human.
