Trifling White Women with Roy Wood Jr.

Summary

Dear Chelsea Podcast: "Trifling White Women with Roy Wood Jr."

Release Date: November 27, 2025
Host: Chelsea Handler
Co-host: Kathryn Law
Guest: Roy Wood Jr.

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Overview

In this engaging, heartfelt, and often hilarious episode, Chelsea Handler and co-host Kathryn Law welcome comedian, author, and TV host Roy Wood Jr. for a candid conversation about family, fatherhood, personal growth, and the realities of show business. Roy shares stories from his compelling new memoir, reflecting on his upbringing, complex relationships with parents, how his childhood shaped his worldview, and the challenges of raising a son. The discussion weaves through themes of race, discipline, forgiveness, career pivots, and authenticity in both comedy and life. They also take listener questions focused on creative careers and the intersection of personal and professional boundaries.

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Key Discussion Points & Insights

1. Roy’s Family Background and Parental Dynamics

• Mother's Sacrifice and Strength
  • Roy describes his early years living with his mother, then moving in with his father for more structure as he began to "act up."
  • "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." (06:25, Roy)
• Open Relationship and Father’s Other Family
  • His mother tolerated his father’s relationships with other women but set boundaries:
    • "My mom was very gangster… she’s talked a lot of shit to a lot of people in strange places and could have paid a much larger price." (08:12, Roy)
  • Roy recounts an incident when his mom chased off a woman with a bat (09:04).
• Impact on Roy’s Views on Marriage
  • Seeing his parents’ arrangement left Roy with a pragmatic—not romanticized—view on marriage:
    • "You’re not going to tell me everybody that is married is successful and truly happy." (09:14, Roy)

2. Upbringing, Discipline, and Community Lessons

• Discipline Through Tough Love
  • Roy’s parents, especially his mom, practiced tough love—examples included being left alone during tantrums in stores:
    • "That white lady was trying to help, but she didn't know she was interrupting an important lesson about discipline." (17:00, Roy)
• Race, Community, and Generational Trauma
  • Roy talks about his mom’s experiences integrating the segregated Delta State University and prevailing through Jim Crow Mississippi.
  • Unpacking family trauma: Roy's father lost his own dad at age 4 under suspicious conditions in 1930s Georgia, leading to cycles of abandonment and emotional reserve in the family (20:27).

3. Father’s Influence and Career Inspiration

• Father as a “Civil Rights Journalist”
  • Roy’s father was a radio journalist and activist, and Roy often tagged along to interviews and events, learning early about Black leadership and building resilience.
• Learning Resourcefulness
  • Roy became self-sufficient young, running small businesses like raking leaves to make ends meet (13:17).
• Reflecting on Differences Between Siblings
  • Roy notes the disparity in experiences with his half-siblings, who had a different, more stable side of their father during their childhoods:
    • “It’s not ideal. It wasn’t cool. But as I got older and I had a son… I have to look to my dad and the other woman and I have to unpack that.” (20:27, Roy)

4. Healing, Forgiveness & Parenting

• The Importance of Forgiveness
  • Roy speaks to understanding and accepting parents’ flaws:
    • "Forgiveness without forgetting is probably the best bucket to put it in for however our parents failed us..." (20:27, Roy)
• Breaking Cycles as a Parent
  • Roy doesn’t obsess over legacy, but wants to create for his son “the version of myself that I wish I had been.” (10:36, Roy)
• Inner Child Healing
  • "Trying to raise a child before healing your inner child is a motherfucker." (27:51, Roy)
  • Roy shares he recently bought himself the Voltron lion toy he cried for as a child, addressing small wounds from his past to better show up for his own son (28:03).

5. Encounters with ‘Trifling White Women’ (Episode Title Reference)

• White Women as Unintended Interveners
  • Roy recounts being left by his mom in a store to teach discipline, thwarted by a concerned white woman. Later, white employees intervened when he was briefly lost at a Macy’s, illustrating both protection and the mistrust his mom held about outsider involvement (17:00).
• Casual Racism Experience
  • In college, Roy describes being pre-emptively told by a sales clerk, “We don’t have layaway,” then ironically realizing he did need it (19:08):
    • “We needed layaway… so we spent the next 30 minutes in the store pretending we have money because we didn’t want her to think we don’t have money, because that’s how you fight racism. It’s just aggressive browsing.”

6. Showbiz, Setbacks & Pivots

• Failure is Part of the Game
  • Roy and Chelsea swap painful tales of bombing in comedy and navigating public failure:
    • “As soon as I walked on stage, I knew I picked the wrong jokes… I ate shit at the Apollo.” (36:13, Roy)
• Resilience & New Opportunities
  • Roy explains why he left "The Daily Show" without another job lined up, citing organizational uncertainty, desire for creative growth, and the need to seize fleeting opportunity:
    • “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.” (43:29, Roy)
  • He attributes his transition to CNN’s "Have I Got News For You" to this leap of faith.

7. Advice to Listeners & Aspiring Creatives

• On Comparison and Career Trajectories

  • Danielle, a mid-career comic and therapist, seeks advice on blending her comedy and psychology backgrounds:
    • Chelsea and Roy stress not to compare oneself to others, and to leverage unique perspective and community.
    • “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.” (53:19, Roy)
  • Encourages leaning into personal authenticity, especially in comedy, rather than chasing generic success or stardom:
    • “If you think of comedy as a relationship and you 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?” (58:22, Roy)

• On Dating in the Industry & Stigma

  • Listener Carrie is concerned about the “chuckle fucker” label for women dating comedians:
    • Roy: “Chuckle fuckers are not people that are within the industry. Cops fuck cops. Sometimes they fuck firefighters. I think you shoot your shot.” (66:57)
    • Kathryn: “Who cares? My God, we’re all gonna die soon anyway. Doesn’t fucking matter.” (67:32)

8. Roy’s Political Perspective

• Media, Speech, and Control
  • On current U.S. politics:
    • “If we are not careful [the next administration] 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 … That part, you know, scares me for sure.” (68:42, Roy)
  • He sees comedians (and, humorously, strippers) as the “tip of the spear” for free speech and resistance.

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Notable Quotes & Memorable Moments

• Roy on resilience:
  • “Trying to raise a child before healing your inner child is a motherfucker.” (27:51, Roy)
• On career pivots:
  • “It’s the most familiar feeling I have is not knowing what the hell is next.” (43:29, Roy)
• On comedy and authenticity:
  • “If you think of comedy as a relationship and you 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?” (58:22, Roy)
• On industry dating stigmas:
  • “Chuckle fuckers are not people that are within the industry. You’re just somebody in the industry dating people in the industry.” (66:57, Roy)
• Kathryn on labels:
  • “Who cares? My God, we’re all gonna die soon anyway. Doesn’t fucking matter.” (67:32, Kathryn)

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Timestamps for Important Segments

• Introductions and Tour Announcements: (03:43–05:10)
• Roy's Family Story—Early Upbringing & Parental Relationships: (06:25–10:31)
• Impact of Father’s Other Family; Mom’s Boundaries: (07:14–09:11)
• Roy’s Take on Marriage & Parenting: (09:14–11:33)
• Father’s Life, Work, and Influence: (11:48–13:17)
• Childhood Lessons and Latchkey Experiences: (13:54–16:37)
• Disciplinary Stories & “Trifling White Women”: (17:00–18:57)
• Reflections on Father’s Trauma & Forgiveness: (20:27–26:00)
• Healing Inner Child with Voltron Lion: (27:51–28:03)
• Story: Almost a Victim of Grooming: (29:40–34:45)
• Bombing at the Apollo and Career Setbacks: (35:46–40:10)
• Leaving The Daily Show / Navigating Uncertainty: (40:10–47:28)
• Listener Question: Should I Niche Down My Comedy? (51:07–61:00)
• Listener Question: Dating Comedians & Stigma (66:11–68:16)
• Roy’s View on Politics, Free Speech: (68:30–69:51)

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Conclusion & Takeaways

This episode is a raw, intimate, and comedic journey through Roy Wood Jr.’s life, the hard lessons of family and race, the unpredictability of showbiz, and the mental gymnastics of parenting and personal growth. Listeners are left with reflections on breaking generational cycles, the importance of self-forgiveness, and the value of staying true to oneself—onstage and off. The advice to listeners is practical, heartfelt, and rooted in the hosts' and guest’s hard-won wisdom.

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For more, check out Roy Wood Jr.’s new memoir, The Man of Many Fathers, and catch him on CNN’s Have I Got News For You.

Transcript

[Chelsea Handler]

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[Kathryn Law]

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[Kathryn Law]

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 Mesa, Arizona Kansas City, Missouri St. Louis, Missouri Minneapolis, Minnesota Nashville, Tennessee Charlotte, North Carolina Durham, North Carolina Saratoga, California Monterey, California Modesto, 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 on the High and Mighty Tour. Hi Katherine.

[Chelsea Handler]

Hi Chelsea.

[Kathryn Law]

How are you?

[Chelsea Handler]

I'm wonderful. And you're in Antarctica right now, so.

[Kathryn Law]

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 gonna download everyone when I get back.

[Chelsea Handler]

I'm so excited.

[Kathryn Law]

It has been transcendental.

[Chelsea Handler]

Well, since everybody is dealing with Thanksgiving stuff, we'll get right into it. But our guest today had a great bug.

[Kathryn Law]

I really 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 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, like 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.

[Roy Wood Jr.]

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. Cause 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.

[Kathryn Law]

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

[Roy Wood Jr.]

Third grade, so.

[Kathryn Law]

But you talk in the book. We're gonna 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 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.

[Guest/Caller]

No.

[Roy Wood Jr.]

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 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 was 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, 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 going to get. You going to get slapped up?

[Kathryn Law]

Well, you're going to. She's going to come back with a bat is what happens in the book.

[Roy Wood Jr.]

Yeah, my bat. I couldn't even use it anymore literally after that, because the glass, that's a separate conversation.

[Kathryn Law]

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

[Roy Wood Jr.]

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. 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. And that's the question married people never answer.

[Kathryn Law]

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.

[Chelsea Handler]

You can't really unload them either.

[Roy Wood Jr.]

Yeah. Nobody wants to raise the murderer.

[Kathryn Law]

No.

[Roy Wood Jr.]

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. And, like, I didn't name him Roy Wood iii. I wouldn't dare.

[Kathryn Law]

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.

[Roy Wood Jr.]

Yeah.

[Kathryn Law]

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?

[Roy Wood Jr.]

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.

[Kathryn Law]

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? 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 had already finished your school year because he didn't want you hanging around the house, which I think is a clutch move, actually.

[Roy Wood Jr.]

He didn't even enroll me. He just took me to the school. Cause I would spend. 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. And knowing what I know now, it's probably some teacher. He Was. 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 putt putt or have a fun cool Father's Day. 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.

[Kathryn Law]

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. Cause in the book, he tells one of my favorite stories, or the one that resonated with me the most. Cause 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?

[Roy Wood Jr.]

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 another hour to go to get home.

[Kathryn Law]

And what was the temperature?

[Roy Wood Jr.]

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. And 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, 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.

[Kathryn Law]

I know that was a very nice touch to that story. You think it's almost a misdirect. You think he is gonna molest you. And instead he's like, you know what? I'll save my drink until after I.

[Roy Wood Jr.]

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.

[Kathryn Law]

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, 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, you know, 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.

[Roy Wood Jr.]

I was the only child in that house with my parents. How y' all not notice that I'm not here yet?

[Chelsea Handler]

Yeah, the fact that they both each thought the other was gonna get you, but neither of them looked at each other and was like, where's Roy? When they got home.

[Roy Wood Jr.]

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.

[Kathryn Law]

You tell a story about being a kid and getting in 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 wanna know, in what other ways have trifling white women impacted your life?

[Roy Wood Jr.]

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 gonna argue with you. If you wanna have a temper tantrum about a fucking Voltron lion, I'm Just gonna leave you in the mall. And my mom walked off, and the poor little white lady. Miss. You left your son.

[Guest/Caller]

Miss.

[Roy Wood Jr.]

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 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's and hands it to me. And then I'm just on the mic. Mama, where are you? I'm in lemon stockings. This Roy click. And my mom comes over, furious, cusses out the white lady. My mom is 1000% 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.

[Kathryn Law]

Yeah, right.

[Roy Wood Jr.]

That's all her thoughts 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?

[Kathryn Law]

Which. A partner of yours? What do you mean, a partner of yours? Well, I'm not the one to answer that. Roy, as, you know.

[Roy Wood Jr.]

Set you up.

[Kathryn Law]

What was the other experience?

[Roy Wood Jr.]

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 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 doing? Can I help you? My name is Yvonne. Whatever. And we go, we don't need layaway. 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 a thou. It's a leather jacket. That shit starts at $1,000. We thought this would be $150 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. So let's just kept trying on shit.

[Kathryn Law]

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?

[Roy Wood Jr.]

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 siblings, 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 4. 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 pops was pretty much fucked from age 4, and we were 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 in the 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 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. My two young. 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 and pops and they got the old school Polaroid Kodak joints that 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 posted 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 gotta 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. And if I'm gonna 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 standup, I don't talk about my life. I don't talk about. 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 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 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.

[Kathryn Law]

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. Up sexually a couple months ago, but I don't know if that panned out or not.

[Roy Wood Jr.]

That person would not want two partners either, just so you know that. 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. Runs not the right word, but I'll 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 correspondents dinner and afterwards, just random black people are coming. Yeah, Your dad in 1971 got me my first pepper pie. And then I remember I needed a tape recorder. And we was at the press and your daddy loaned me 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 who your parents are if you're gonna 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.

[Kathryn Law]

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?

[Roy Wood Jr.]

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 80s.

[Guest/Caller]

And.

[Roy Wood Jr.]

I saw it at like a collectible store. I was like, yeah, I'm gonna 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 watch 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 is 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 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 I had to grow up a little faster.

[Guest/Caller]

Right.

[Roy Wood Jr.]

You know?

[Guest/Caller]

Yeah.

[Kathryn Law]

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.

[Roy Wood Jr.]

Oh, it's illegal. Not what we were doing. Oh. They would have taken me away from my mom in a heartbeat.

[Kathryn Law]

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

[Roy Wood Jr.]

Is that how you classified?

[Kathryn Law]

That's how I classified it, yeah. Why don't you tell us that story?

[Roy Wood Jr.]

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, 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?

[Kathryn Law]

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.

[Roy Wood Jr.]

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.

[Kathryn Law]

Well, tell me, can you give us. Give us the story. Give our listeners a little version or the abridged version of that story.

[Roy Wood Jr.]

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. I had a supervisor who did not live on my side of town. There were co workers 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 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 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 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 to 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 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, GD's out here, the gangster disciples, they out here. GDS will 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 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. Your dick's flapping. You don't have on enough clothes. Go back, put some draws on, and. 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.

[Kathryn Law]

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

[Roy Wood Jr.]

He's in nothing but a towel, freshly showered. Both of them still got 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 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 had 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 not gonna do that shit today, bro. My mama waiting on me. And you can see them kind of both look at each other and they're like asking me like very like non hospital questions about, you know, do you. When's 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 gotta get the 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.

[Kathryn Law]

Yeah, I would think that those confirmed, you know, like, in case you're mistaken, that was confirmed when they came out in bath towels.

[Roy Wood Jr.]

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.

[Kathryn Law]

Are you?

[Roy Wood Jr.]

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.

[Kathryn Law]

Or out of some moral compass to do the right thing.

[Roy Wood Jr.]

Yeah. Or they just trying to fuck on the couch.

[Kathryn Law]

Right, right. Another similarity we have, you and I, is I had a big bomb at the Montreal Comedy Festival 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 wanted to. I want you to talk a little bit about when your life changing moment doesn't. The moment that you want it to be.

[Roy Wood Jr.]

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

[Kathryn Law]

It was so. I didn't get booed, I bombed. But no one booed me. But I mean it was 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 sickening. It was sickening. I was so mortified at my own existence.

[Roy Wood Jr.]

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 him with the good jokes wrong. And I had already had in my head like how it was gonna play out. Cause Apollo, this is my first ever TV gig. This is 02. 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 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. Katt 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. Two 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 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 gotta go back out and get Kiki shepherded where she, you know, they put the hand over your head to judge. And I give it up for the first comedian. Yeah, give it up for Roy Wood 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 everything 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 in Times Square. But I went there and had a Big Mac meal, high sea 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 and 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 had done Apollo same day, got booed. And we get back to the hotel. We're staying at the Knights Inn in Elizabeth, New Jersey. And it's all open air prostitution and drugs, like the whole street. I don't know what it is. Now I know that Nights Inn is still there, number one, but. 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 like we'd 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 touching. Like, I almost paid for some sex that night out of respect.

[Kathryn Law]

Have you ever paid for sex, Roy?

[Roy Wood Jr.]

Not outright, but.

[Kathryn Law]

Right.

[Guest/Caller]

Copy that.

[Roy Wood Jr.]

In theory, all men have. Like, not like, give me a Venmo. Thanks a lot. Not like that.

[Kathryn Law]

Let's talk about walking away from jobs. Another element that you and I have in common. What was your final decision and 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?

[Roy Wood Jr.]

No.

[Kathryn Law]

You didn't have that job lined up?

[Roy Wood Jr.]

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 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 paranoia of the merger. I was, look, I don't know how you felt at the time with all the guest hosting and your name being in the hat. I was hyper paranoid about the merger in what way? And the pending Paramount Skydance, which finally happened. Now, that was cooking back then.

[Kathryn Law]

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

[Roy Wood Jr.]

Because the first thing you do is 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.

[Kathryn Law]

Well, it's the same people.

[Roy Wood Jr.]

Just guess host.

[Kathryn Law]

Right, right, right. The same people that run Colbert did run the Daily Show.

[Roy Wood Jr.]

Okay, so now you're coming off of the writer strike. You get a call from Comedy Central and they go, what's up? You 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 gonna find the 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? Jon 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. Cuz 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 correspondence. And if you're gonna cut correspondence I bet you cut from the top, from the highest salary, longest tenure people. This is just where my doomsday 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 wanna 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 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 unlocked 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.

[Kathryn Law]

Prescient. Very prescient.

[Roy Wood Jr.]

Come on, quit.

[Kathryn Law]

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 gonna 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.

[Roy Wood Jr.]

Trust yourself. Cause they won't reveal themselves. Cnn. I wouldn't have if I was under contract with Daily show for another year. The CNN wouldn' call because, I mean, essentially 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 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. Cause I thought there was still room for a new show or a new idea. There was not. So, you know, I'm not gonna 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 a script. Yeah. I mean, you quit the Daily Show. You'll be hot for at least two months. That's, you know, 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 the earth. You got two windows of reentry. You missed this reentry. You gotta circle off all the way back around and run out of gas. 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.

[Kathryn Law]

Yeah, right, Exactly. I love that. We're going to take a break and we'll be right back with Roy Wood.

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[Chelsea Handler]

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 standup 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 Westside 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 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 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?

[Roy Wood Jr.]

No.

[Chelsea Handler]

How do I keep moving forward without abandoning my self comparison or self doubt? Danielle?

[Kathryn Law]

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.

[Roy Wood Jr.]

Hello, Danielle. One time for the west side with the good Mexican food upstairs.

[Kathryn Law]

Right on. First of all, don't gear your casinos suck, okay? Just so you know, I'm saying, I mean, you know, 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?

[Roy Wood Jr.]

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 Youngins. It's a leapfrog 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 real world experience. Like, you didn't just do this forever. Like you've had regular jobs and shit. You've got. Had an experience. I think that you lean into the material that'll 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 10 years ago, I'd have told you, be broad and 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. I'm trying to think of like some of the other standups that just went off and did their own thing. I'm just over here doing a pot. Mark Marin'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 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, let's just say 1,000 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 are on, who feel like they're on the outside looking in, look at stardom as the only form of success. You could go do those corporate. I bet you one of them therapy conferences will pay your ass 25k to 100k to eventually. 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 Corp 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 standup, 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. Cause 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.

[Kathryn Law]

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 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 gonna 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? You're the one who's making decisions around yourself and around your career and what you're gonna 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, an mfaa or did 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? 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 feel like you bombed is when you're not confident, you know, because you can smell that it tried.

[Roy Wood Jr.]

To be something you weren't for an audience that was never going to appreciate the truest version of you. So now you just. It's like, but if you think of comedy as a relationship and you 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?

[Chelsea Handler]

That's a great analogy.

[Roy Wood Jr.]

Yeah. 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 act like I Write the tightest 4 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 at a different octave. You can 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 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 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.

[Kathryn Law]

Yeah, through the lens of therapy is a good idea too. You know, that's interesting commenting on like world events, pop culture, whatever you're the most passionate about through the lens of, of therapy with that bent.

[Chelsea Handler]

Well, and I think mental health and therapy stuff like does play more broadly nowadays. Like we all have that language. It's become de rigueur. I also want to say that CorpGesture.com is alive and well. So Mark Klein is out there doing a thing.

[Roy Wood Jr.]

Wow, look at him. Shout out to Mark Klein.

[Kathryn Law]

Awesome. Okay, well I hope that was helpful, Danielle.

[Guest/Caller]

Very.

[Chelsea Handler]

I really appreciate it. Thank you so much for taking the time.

[Kathryn Law]

Sure. Nice to meet you both. Nice to meet you, Danielle. Nice to see you, Katherine. Thank you. We're going to take a quick break and we'll be right back with Roy Wood. From nursing and healthcare to business and it, Rasmussen has a range of programs to fit your goals and passion no matter what your day to day looks like. Rasmussen's programs allow you to balance school with life while you pursue your degree. So if you're ready to pursue your education goals, Rasmussen is ready to help you take that next next step. Head on over to Rasmussen. Edu and check out the opportunities waiting for you. Your future is a bright one. Rasmussen University can help you get there.

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[Guest/Caller]

You know what's not fun?

[Kathryn Law]

Waking up at 2am drenched in sweat. Been there.

[Guest/Caller]

That's why I started using pod 5 from 8 sleep and let me tell you, it is a game changer. It's designed with women's help in mind, especially for those of us dealing with hot flashes. Pod 5 is this genius smart mattress cover that fits over any bed and pulls your body before a hot flash can mess with your sleep. And when I need an extra relief, I just tap the bed or use the app to activate hot flash mode. 30 minutes of instant cooling. It's like having a personal climate concierge. It's clinically proven to reduce hot flashes by over 50% and I genuinely sleep deeper and wake up feeling way more refreshed. I love that it's a non medical solution, but it's backed by real data and it feels totally natural. Anyone who listens to this podcast knows that I would like to sleep in a refrigerator and now I can. And if you sleep with a partner, Pod 5 cools each side of the bed independently. So no more kicking someone out for being a human furnace. You both get your perfect temperature from 55 degrees to 110 degrees.

[Kathryn Law]

Go to eightsleep.com Chelsea use code Chelsea and get up to 700 off pod 5. You can try it risk free for 30 days. Trust me. Better sleep starts here. You know that feeling when you come home late from work and those puppy dog eyes just pierce right through your soul? Or when you're packing for a trip and your cat refuses to leave your suitcase? Yep, we've all been there. Pet parent guilt is real. And you know what? It's completely normal. That's exactly why Hill's Pet Nutrition exists. They understand that being a pet parent means being human. With all of our imperfections and daily juggling acts, Hill's science led nutrition helps you give more love than humanly possible. Whether it's those long work days or trying to balance attention between multiple pets, Hill's Pet Nutrition gets it. They've created science based nutrition that supports your pet's lifelong health so that you can feel confident even when life gets hectic because you're only human. There's Hills. Science does more Ready to let go of the guilt? Find the right [e-mail] iheartra that's hillspet.com iheart the holidays are here, which means I am stressed, over, committed, slightly buzzed and pretending I know how to cook. But at least my dog Doug is thriving. He's eating just fresh from just food for dogs. Real human grade food with none of that processed junk. It's shelf stable, which means I can toss it in my suitcase when I travel or shove it in a cabinet next to my tequila. And honestly, Doug's living his best life. His coat is shiny, he's got energy, and when guests come over, he's the only one not complaining about their food. Meanwhile, I'm over here eating takeout and calling it festive. So this holiday season, give your dog something better than table scraps. Give them just fresh, real food for dogs who have better taste than we do. Go to justfood4dogs.com for 60% off your first order during their holiday promo. No code, no hassle, and lucky for dogs, still no cooking required. And we're back with Roy Wood, junior and Senior.

[Chelsea Handler]

Okay, so our last question comes from Carrie. This one's just an email. She says, dear Chelsea, I'm not a standup 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 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?

[Kathryn Law]

Yeah, fuck it. What do you care? What. What's a chuckle fucker anyway? I mean, who gives a shit what anyone thinks? If you like funny men, you like funny men.

[Roy Wood Jr.]

Also, chuckle fuckers 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 and just, you know.

[Kathryn Law]

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. Doesn't fucking matter.

[Roy Wood Jr.]

Yeah, I don't know how old that person is, but once they get into the 30s, you're gonna realize that there's a couple of comics that have all cross pollinated and you know, never openly dated one. Not as like a title of girlfriend, but I've dated like two or three comedians.

[Kathryn Law]

Well, I think you and Yamanika should start dating. That's my don't start rumors.

[Roy Wood Jr.]

Don't, don't start.

[Kathryn Law]

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

[Roy Wood Jr.]

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.

[Kathryn Law]

You go, Roy, I just want to know, since you have a political show and you're a political commentator, how do you see what's your view or long lens of our current political situation? How do you see things?

[Roy Wood Jr.]

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. Cause the strippers be dancing for the politicians.

[Kathryn Law]

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 your. 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.

[Guest/Caller]

Fair.

[Kathryn Law]

I'm glad to be a woman. I'm proud of our female listener readers. And who needs straight men anyway? Thank you, Roy.

[Roy Wood Jr.]

Wait a minute now. Okay.

[Kathryn Law]

And on that note, congratulations Roy. We love you. Thank you for coming on.

[Chelsea Handler]

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.

[Kathryn Law]

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.

[Chelsea Handler]

Do you want advice from Chelsea? Write in to dearchelsea podcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching ear Chelsea Pod Dear Chelsea is edited and engineered by Brad Dickert Executive Producer Kathryn Law. And be sure to check out our merch@chelsea handler.com.

[Kathryn Law]

You know that feeling when you come home late from work and those puppy dog eyes just pierce right through your soul? Yep, we've all been there. Pet parent guilt is real and completely normal. That's exactly why Hill's Pet Nutrition exists. They understand that being a pet parent means being human. Hill's science led nutrition helps you give more love than humanly possible, whether it's those long work days or trying to balance the tension between multiple pets. Hills Pet Nutrition gets it because you're only human. There's Hills. Science does more Ready to let go of the guilt? Find the right [e-mail] iheart that's hillspet.com iheart from nursing and healthcare to business and it Rasmussen has a range of programs to fit your goals and passion no matter what your day to day looks like. Rasmussen's programs allow you to balance school with life while you pursue your degree. So if you're ready to pursue your education goals, Rasmussen is ready to help you take that next step. Head on over to Rasmussen. Edu and check out the opportunities waiting for you. Your future is a bright one. Rasmussen University can help you get there. I used to wake up at 2am.

[Guest/Caller]

Drenched in my own sweat. Not the cutest. Then I found pod 5 from 8 sleep and it changed everything. It's built with women's health in mind and helps with those brutal hot flashes. It is a smart mattress cover that cools your body before a hot flash hits. And when I need an instant relief, I just tap the bed to use the app to activate hot flash mode. It's clinically proven to reduce hot flashes by over 50% and it even cools each side of the bed independently.

[Kathryn Law]

Go to eightsleep.com Chelsea use code Chelsea and get up to $700 off Pod 5. You'll thank me later. Then the space hamster flew his hot air balloon all the way to the bottom of the ocean.

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[Kathryn Law]

Nope.

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[Roy Wood Jr.]

Honestly, Honestly, Honestly, no one wants to think about hiv, but there are things that everyone can do to help prevent it. Things like prep. PREP stands for Pre Exposure Prophylaxis, and it means routinely taking prescription medicine before you're exposed to HIV to help reduce your chances of getting it. Prep can be about 99% effective when taken as prescribed. It doesn't protect against other STIs, though, so be sure to use condoms and other healthy sex practices. Ask a healthcare provider about all your prevention Options and visit findoutaboutprep.com to learn more. Sponsored by Gilead this is an iHeart podcast.

[Chelsea Handler]

Guaranteed human.