Life Will Be the Death of Me with Chelsea Handler - Trifling White Women with Roy Wood Jr.

Episode Date: November 27, 2025

The 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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Starting point is 00:01:42 The cast of Frozen stopped by. Kristen Bell, Josh Gad, and Idina Menzel. I auditioned for Frozen. What? For Kristoff. They said, okay, what are you going to be singing today? I said, I don't know. That must have been why you didn't get it.
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Starting point is 00:02:37 Apple Podcasts, or wherever you get your podcasts. 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,
Starting point is 00:03:17 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 be on the High and Mighty Tour. Hi, Katherine. Hi, Chelsea. How are you? I'm wonderful. And you're in an article right now. I am in the Southern Hemisphere right now. I am hiding in a closet, recording this introduction to you. I can't tell you what's going on yet because I'm going to download everyone when I get back. I'm so excited. But it has been transcendental. Well, since everybody is
Starting point is 00:04:05 dealing with Thanksgiving stuff, we'll get right into it. 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, 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
Starting point is 00:04:56 relationship with your mother more specifically and your relationship with your father. So let's start there with your relationship with your father, because you didn't really start out living with your father your mom and you you guys lived alone for a while and then you started to get into a little bit of trouble and she decided to move so that you could be close to your father so she essentially got back together with your father in a kind of open relationship because you started to act up yeah now that i'm older i can say i don't think she ever got back with him she moved in we moved back in with them which is a different dynamic because they never slept in the same bedroom like my parents never as far as I know ever had sex again but the idea of
Starting point is 00:05:44 I'm a single mom I work all day I'm in grad school all night I cannot keep an eye on him I will lose him to the streets if I don't make this choice so in a lot of ways I think that my mother sacrificed her own happiness and comfort in a way to ensure that I had some degree of upbringing, having a male in the house. So you guys moved to Birmingham, right? When you moved back in with your father. Okay. Correct. Third grade. So, but you talk in the book, we're going to jump around a little bit because in the book, since you just brought it up in the book, you talk about your dad's other, you know, he had, 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, your, your
Starting point is 00:06:30 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 gonna fucking leave you in the meantime these women are not going to be so blatant with the disrespect that they think
Starting point is 00:07:13 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're gonna get you're gonna get slapped up well you're gonna she's gonna come
Starting point is 00:08:00 back with a bat is what happens in the book yeah my bat and she I couldn't even use it anymore literally after that because the glass and 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, 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? And that's the question married people never answer. Right, right. Exactly. It's
Starting point is 00:08:49 kind of like when you talk about raising a child I mean I find it analogous to that only because I've done neither of those things when you think about raising a child and all the things that come along with it it's like how many moments of bliss are there obviously you love this person more than anything else in the world but how many moments of bliss compared to the moments of stress and agony and all of the other things that come with it and how how do those moments of bliss just overpower all of the other stuff you know it's kind of similar to marriage like it can't be i guess it has to be more good than bad but raising a kid you know if you get an if you get an off one or one that's not cooperative that's fucking stressful you can't really unload them
Starting point is 00:09:32 either yeah nobody wants to raise the murderer no and i'm sure they didn't set out to do things that made their child commit crimes. But with my son, I'll say this. It feels like an opportunity for me to create the version of myself that I wish I had been, and then to set that out into the world to better the world, if you will. That idea of it, you know, I'm not really caught up in legacy. Like, I didn't name him Roy Wood III.
Starting point is 00:10:04 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.
Starting point is 00:10:32 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 like he 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
Starting point is 00:11:27 He didn't even enroll me. He just took me to the school because I would spend the first month. 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 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.
Starting point is 00:11:55 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 it's literally hey man Jesse Jackson's in town for the Democratic National Convention I'm gonna go interview him you're coming bring a snack and that was it and if you could pay for it yourself even better because his dad was hugely penurious, didn't want him to spend any money. So Roy, like myself, was very resourceful as a young person, creating his own business, raking leaves, drumming up a lot of business. Also, we have something in common, which I texted you about last week is in the book, he tells one of my favorite stories or the one that resonated with me the most,
Starting point is 00:12:40 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 that. 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.
Starting point is 00:13:07 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 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 like you're talking those in that era in the 90s don't take
Starting point is 00:13:41 a ride from a stranger and i'm like fuck it bro even if you're gonna molest me i bet you got a heater so let's do it and the guy god bless him was a drunk but he cared enough to cap the liquor and not drink and drive while he took me home i know that was a very nice touch to that story you think it's a 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 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.
Starting point is 00:14:27 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 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. I was the only child in that
Starting point is 00:15:09 house with my parents. How y'all not notice 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 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 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
Starting point is 00:15:46 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 right 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 want to have a temper tantrum about a fucking voltron lion i'm just gonna leave you in the mall and my mom walked off 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
Starting point is 00:16:38 galleria and a white lady comes over and sir what's going on and i'm gonna i'm gonna help you and what's going on baby what's your mother's name 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 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 but because in my mom's mind it's they're going to take you from me yeah right that's all that's all her thought was that you called the police you you called you have involved an employee who will
Starting point is 00:17:33 involve management who will involve the police so my mom had to come in on the offensive and just immediately like cuss her out like that that's that's really the most really weird white women And 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.
Starting point is 00:18:05 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 doing shit can I help you my name is Eva whatever and we go we don't need layaway we 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
Starting point is 00:18:45 layaway them shits was like a thousand it's a leather jacket that's just 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 a thousand dollars 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 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
Starting point is 00:19:31 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
Starting point is 00:20:02 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. I know all my half siblings, but his extended family tree, never met him. So I found out that my grandfather was killed when my dad was four. Well, he disappeared in the night without a trace
Starting point is 00:20:25 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 i walked away from that television show that day just understanding that my pops was pretty much fucked from age four and we were solidified at age 16 and anything else he became he became as a byproduct of trying to get past
Starting point is 00:21:28 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 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 my two young I'm closest to them because we're closest in age and with me in the older halves it's a 20-year age
Starting point is 00:22:25 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 but 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
Starting point is 00:23:21 just got to respect it Chelsea like it's not ideal it wasn't cool but as I got older and I had a son and I started thinking about the idea of showing him love and what does love look like and well what were the examples I had of love, I have to look to my dad and the other woman. I have to. And I have to unpack that. If 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 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 I look at the choices he
Starting point is 00:24:14 made and I really feel like my pops didn't understand how to get love right until the end until the 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. 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
Starting point is 00:25:08 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. I have one child that I co-parent with his mom and that's great I've I love what I do and I think part of it where I feel like there's similarities between me and my dad is comedy is the one place that makes me feel alive entertaining and writing and creating everything else falls second so when there are huge responsibilities and big things that I have to take care of I might I don't run's 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
Starting point is 00:26:05 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 have come 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 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 going to figure out who you are and what the best parts of them are so that you can take that
Starting point is 00:26:49 and pass that on to your children. You opened the book by saying, trying to raise a child before healing your inner child is a motherfucker. So where, what, do you feel like you've healed your inner child? Getting there. Oh, guess what I bought about a month ago?
Starting point is 00:27:07 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. It's mine now. I don't have it on one of these days. It'll make it to this shelf.
Starting point is 00:27:29 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 was working her ass off two jobs in night school and law school and grad school I don't want to bother her
Starting point is 00:28:05 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 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 what it means today oh it's illegal not 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
Starting point is 00:28:59 right right like make sure no one touches your breasts they never tell you how perverts spit game is that is that a bet is that a better way of 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 it's more industry angling what 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 well tell us can you
Starting point is 00:29:49 give us give us the story give our listeners a little version or the abridged version of that story I worked at a hospital in the cafeteria and my supervisor used to give me rides home from work if my car was broken down that week at a supervisor who did not live on my side of town there were 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're doing and talk about girls I'm 16 for context this 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
Starting point is 00:30:37 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
Starting point is 00:31:09 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 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 gangsta disciples they out here
Starting point is 00:31:24 GD's 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 draws on and and he comes in and he sits on the couch and starts making small talk with me
Starting point is 00:32:01 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 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 gonna get kidnapped let them know that you know somebody going to the search will
Starting point is 00:32:52 begin shortly after you snatch me like i don't know what y'all trying to do but whatever it is we're not gonna do that shit today bro i my mama waiting on me and you can see them kind of both looking at you and they're like asking me like very like non-hospital questions about you know do you when's the last time you had sex do you like blowjobs do the girls give you blowjobs 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 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 Which confirmed, you know, like.
Starting point is 00:33:40 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.
Starting point is 00:34:00 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 they just trying to fuck on the couch right right another similarity we have you and I is I had a big bomb at the Montreal Comedy Festival when I right before I got very successful. And you talk about being booed out of the Apollo, and this was supposed
Starting point is 00:34:35 to be your life-changing moment. And so what 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? Oh, 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 uh is sick it was sickening I was so mortified at my own existence I I went it's 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
Starting point is 00:35:24 get to round two that's when i'm gonna really hit him with the good jokes wrong and i i'd already had in my head like how it was gonna 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 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 kat williams don dc curry some more like there's so many black comics that ice cube was just like yeah you you're famous now and i was like this is gonna be my moment and i went out there and i ate shit not only did i eat
Starting point is 00:36:25 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 gonna let me do it i know they're not gonna let me finish the next joke i should leave now so that i don't get booed and i said good night i walk off stage but here's the joke on me you walked off stage that means you got to go back out and get kiki shepherded where she you know they put the hand over your head to judge and like give it up for the first comedian yeah give it up for roy wood jr and the boo was louder than what would have been if i had just taking the original boo and the ride back to the hotel that night was just like so fucking like like it's it's everything you know you're on a high and then immediately you're at your lowest low
Starting point is 00:37:19 and it's gone now r.i.p to the 42nd street mcdonald's in times square but i went there and had a Big Mac meal, 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 and it's just, I don't know what's next. This was the way out. And there's nothing I can do now to change this.
Starting point is 00:37:54 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 Knight's Inn 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 end 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
Starting point is 00:38:49 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 that night out of respect have you ever paid for sex roy not outright but right in theory all men have like Not like, give me a Venmo, thanks a lot. Not like that. Let's talk about walking away from jobs, another element that you and I have in common.
Starting point is 00:39:24 What was your final decision in walking away from the, like, quitting The Daily Show? Did you have the CNN opportunity for your show on CNN, which is called Have I Got News For You? No. You didn't have that job lined up? No, that wasn't even rumored yet. I left Daily Show October of 22.
Starting point is 00:39:45 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 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 like i don't want to sound like somebody from snl whining because my i didn't get enough sketches on i had 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
Starting point is 00:40:30 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 the the pending paramount sky dance which finally happened now that was cooking back then no i know but why 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 the 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 okay that 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
Starting point is 00:41:19 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 a host nope well i know right there i'm not on your shortlist 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
Starting point is 00:42:07 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 correspondents. And if you're going to cut correspondents, I bet you cut from the top, from the highest salary, longest tenured people. This is just where my doomsday brain is going at the time right so they're going to keep guest hosting the merger is 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
Starting point is 00:42:49 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 whoopee the whoopee goldberg sitcom on lock and then it didn't happen so go back out into what you know which is the unknown it's the most familiar feeling I have is not knowing what the hell is next like everybody looked at it as some sort of courageous choice but it's just like no if there's a new show to be made it'll happen this year
Starting point is 00:43:38 I want to be in line for another show prescient very prescient 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 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 saying 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 if i
Starting point is 00:44:23 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 gonna let me out of my deal to go do another show and essentially compete against them during the presidential election year not gonna happen bro so they were never going to do that and then true true to form there were two things that happened after that there were only two shows that came out that year it was the cnn show and after midnight with taylor tomlinson those were the only two and both of those shows are old ip that are remakes so it was even skinnier than i thought it was because i thought there was still room for a new show or a new idea. There was not. So, you know, I'm not going to say I
Starting point is 00:45:08 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'll 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, that, I mean, that's literally how my brain is processing everything
Starting point is 00:46:03 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 re-entry. You miss this re-entry. You got to 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.
Starting point is 00:46:30 We're going to take a break and we'll be right back with Roy Wood Jr. Behind every night spent making the kids' lunches, there's a lot of suspense. Will they finally eat the veggies? Will the pesto survive
Starting point is 00:46:43 the first bite? Will the lunchbox come home empty, half full, or come home at all? And will you finish episode eight before you're done slicing the cucumbers? Get Bell Pure Fiber Internet
Starting point is 00:46:53 with Crave, Netflix, and Disney Plus from $94 a month, price guaranteed for two years on internet with a two-year term and auto pay credit visit bell.ca for details and to check availability bell connection is everything when i was 14 years old i was kidnapped and held captive for nine months i survived and i've spent my life exploring how other people survive what should have destroyed them i'm elizabeth smart and these are the survivor files i just remember this low taunting voice next to my ear saying shut up don't say anything every week i'm with survivors who live through the unthinkable i knew if he woke up
Starting point is 00:47:36 without a doubt he was going to hurt me i started feeling that there was someone at the end of my bed and i just started screaming they are abducted stalked controlled and nearly silenced but these aren't stories about what's taken from them. They're stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page
Starting point is 00:48:07 are equally important to your personality, welcome home. This is Prose Society, the weekly podcast that's part book club, part group chat for thought daughters, pop culture obsessives, and anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. I'm Eli Rallo, and every week we're connecting the dots between books,
Starting point is 00:48:27 the internet, and the conversations everyone can't stop having. I'm going to have to look up this story. I'm obsessed. I'm obsessed. From bestselling authors and your favorite book talk creators to the latest pop culture moments, nothing is off the table. It's like if you can hide some real messages inside compelling characters, then that is a Trojan horse. Whether you're looking for literary deep dives, smart pop culture conversations, or a community of readers who love to think a little too much, you're in the right place. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Starting point is 00:49:04 See you between the pages. Hey, this is Hayes Davenport. And Sean Clements. We host the podcast Hollywood Handbook on the Big Money Players Network. Our show is extremely accessible to first-time listeners. Each week, we talk to someone in show business, a.k.a. the biz, and try to help them with their careers and see what they have to offer us. Everyone has a good time, and no one gets mad at their publicist for letting them do our show. We've had a lot of great guests like Sarah Sherman.
Starting point is 00:49:28 Not that great. Actually, can you help me shape this? How about we flip it on its head? How about we flip the script? What if the surprise woman, who actually you think is the straight man, is actually the one who's acting weird? weird adam scott this entire time you've been expecting adam sandler to come to visit the show i i would never let go of that i have i would never set expectations for something like that it seems like if the universe allows for something like that to happen i'm open to it i'm always
Starting point is 00:50:04 going to accept you know danny mcbride fine yeah it's all this fragile masculinity exuding i could smell it walking down the hallway to be honest with you i was like is that weed nope it's fragile masculinity yeah ben stiller no because a lot of times in out of context people don't get it or even know what a circle is you know what i mean like you're like oh what's this everyone's so dumb and fake right fake and and also not interested or just like oh i've got my life i don't care about your life and a lot of other big shots that wouldn't be where they are without us oh and by the way will ferrell told us personally he loves the show and he wants to be a guest on every episode but he's just so busy listen to hollywood handbook on the iheart radio app
Starting point is 00:50:50 apple podcasts or wherever you get your podcasts on the new podcast solita we share the messy reality of traveling alone as a woman i can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle i chose option b i'm julie pinero and i travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word solita, trading the pity for possibility. Every time I tried to be alone, I kept meeting people
Starting point is 00:51:23 and they were like, you smiled at us. Not a lot of people smile around here. It's when you're alone that you're most receptive to the world as it is and not the lies you're sold about it. It can be a time where you push your limits, change your mind, or wake up to a new version of yourself. So whether you're a solo travel veteran or you're too nervous to book your first trip, I hope you listen to Solita on the iHeartRadio app,
Starting point is 00:51:48 Apple Podcasts, or wherever you get your podcasts. And we're back with Roy Wood Jr. 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.
Starting point is 00:52:19 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 is standup. But clearly that hasn't been entirely true.
Starting point is 00:52:43 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,
Starting point is 00:52:59 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 abandoning myself to comparison or self-doubt? Danielle. Well, first of all, hi, Danielle. How are you?
Starting point is 00:53:28 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. 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.
Starting point is 00:53:51 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.
Starting point is 00:54:11 It's the repetition of it all. Also, you're still stuck on your 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.
Starting point is 00:54:30 you can't compare yourself to the youngins it's a 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 had an experience i think that you lean into the material that'll get you rebooked 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
Starting point is 00:55:19 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,
Starting point is 00:55:39 the Guys We Fucked podcast, 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 part. Mark Maron's a great example where it's just, I'm just going to talk about the things that matter to me
Starting point is 00:55:56 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. Let's just say 1,000 tickets
Starting point is 00:56:17 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,
Starting point is 00:56:41 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 avenge. 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 stand-up. I don't think he had a television credit in the 2000s.
Starting point is 00:57:16 and was living comfortably and great. So it's all about what your idea of success is as well. Because if you could bring humor to the MFA world, there's not a lot of people qualified to even tackle into that. So you could be the beachhead. Also look at Leanne Morgan. I mean, she just hit it.
Starting point is 00:57:35 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.
Starting point is 00:57:56 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? You're the one who's making decisions around yourself and around your career and what you're going to do. And you have to have confidence in that, in and of itself. That's what you're, you're doing something.
Starting point is 00:58:14 How many other people are doing what you're doing? Not, you know, probably not very many who have a degree, an MFA, a, 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.
Starting point is 00:58:36 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
Starting point is 00:58:56 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 you can smell that. You tried to be something you weren't
Starting point is 00:59:14 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, it's 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?
Starting point is 00:59:34 It's a great analogy, yeah. it's just likability and trying to get people to like you enough to go on a journey with you and some 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 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 ways like just
Starting point is 01:00:23 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 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 you know comedy jesus to find us in the back of the comedy clubs
Starting point is 01:01:16 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. Through the lens of therapy is a good
Starting point is 01:01:53 idea, too. Commenting on world events, pop culture, whatever you're the most passionate about, through the lens of therapy with that bent. I think mental health and therapy stuff does play more broadly nowadays. We all have that language. It's become de rigueur.
Starting point is 01:02:10 I also want to say that CorpGester.com is alive and well. Mark Klein is out there doing a scene. Wow, look at him. Shout out to Mark Cronin. Look at that. Awesome. Okay, well, I hope that was helpful, Danielle.
Starting point is 01:02:22 Very. I really appreciate it. Thank you so much for taking the time. Sure. Nice to meet you both. Nice to meet you. Nice to see you, Catherine. Thank you.
Starting point is 01:02:31 We're going to take a quick break, and we'll be right back with Roy Wood. Behind every night spent making the kids' lunches, there's a lot of suspense. Will they finally eat the veggies? Will the pesto survive the first bite? Will the lunchbox come home empty, half full, or come home at all? And will you finish episode 8 before you're done slicing the cucumbers? Get Bell Pure Fiber Internet with Crave, Netflix, and Disney Plus from $94 a month. Price guaranteed for two years on internet with a two-year term and auto pay credit.
Starting point is 01:03:01 Visit bell.ca for details and to check availability. Bell. Connection is everything. When I was 14 years old, I was kidnapped and held captive for nine months. I survived, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are the Survivor Files. I just remember this low, taunting voice next to my ear saying, Shut up. Don't say anything. Every week, I'm with survivors who live through the unthinkable.
Starting point is 01:03:34 I knew if he woke up, without a doubt, he was going to hurt me. I started feeling that there was someone at the end of my bed, and I just started screaming. They are abducted, stalked, controlled, and nearly silenced. But these aren't stories about what's taken from them. They're stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home. This is Prose Society, the weekly podcast that's part book club, part group chat for thought daughters, pop culture obsessives, and anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse.
Starting point is 01:04:25 I'm Eli Rallo, and every week we're connecting the dots between books, the internet, and the conversations everyone can't stop having. I'm going to have to look up this story. I'm obsessed. I'm obsessed. From best-selling authors and your favorite book talk creators to the latest pop culture moments, nothing is off the table. It's like if you can hide some real messages inside compelling characters, then that is a Trojan horse. Whether you're looking for literary deep dives, smart pop culture conversations, or a community of readers who love to think a little too much, you're in the right place. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. See you between the pages.
Starting point is 01:05:06 Hey, this is Hayes Davenport. And Sean Clements. We host the podcast Hollywood Handbook on the Big Money Players Network. Our show is extremely accessible to first-time listeners. Each week, we talk to someone in show business, a.k.a. the biz, and try to help them with their careers and see what they have to offer us. Everyone has a good time, and no one gets mad at their publicist for letting them do our show.
Starting point is 01:05:27 We've had a lot of great guests like Sarah Sherman. Not that great. Actually, can you help me shape this? how about we flip it on its head how about we flip the script what if the surprise woman who actually you think is the straight man is actually the one who's acting
Starting point is 01:05:44 weird Adam Scott this entire time you've been expecting Adam Sandler to come to visit the show I would never expect I would never set expectations for something like that to happen
Starting point is 01:06:00 if the universe allows for something like that to happen i'm open to it i'm always going to accept you know danny mcbride fine yeah it's all this fragile masculinity exuding i could smell it walking down the hallway to be honest with you i was like is that weed nope it's fragile masculinity ben stiller no because a lot of times in out of context people don't get it or even know what a circle is you know what i mean like you're like oh what's this So everyone's so dumb and fake, right? Fake and also not interested or just like, oh, I've got my life.
Starting point is 01:06:37 I don't care about your life. And a lot of other big shots that wouldn't be where they are without us. Oh, and by the way, Will Ferrell told us personally he loves the show and he wants to be a guest on every episode, but he's just so busy. Listen to Hollywood Handbook on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. On the new podcast, Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle. I chose option B. I'm Julie Pinheiro and I travel by myself because it's a rare space where I can say yes without asking anyone else first.
Starting point is 01:07:15 I'm on a mission to reclaim the word solita, trading the pity for possibility. Every time I tried to be alone, I kept meeting people and they were like, you smiled at us. Not a lot of people smile around here. It's when you're alone that you're most receptive to the world as it is and not the lies you're sold about it. It can be a time where you push your limits, change your mind, or wake up to a new version of yourself. So whether you're a solo travel veteran or you're too nervous to book your first trip,
Starting point is 01:07:46 I hope you listen to Solita on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And we're back with Roy Wood Jr. and Sr. 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 frontline act, i.e. entertainer.
Starting point is 01:08:10 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 a 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?
Starting point is 01:08:36 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 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
Starting point is 01:08:56 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 just you know yeah exactly I wouldn't worry about what 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 oh my god we're all gonna die soon anyway it doesn't fucking matter yeah I don't
Starting point is 01:09:38 know how old that person is but once they get into the 30s you're gonna realize that there's all 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 well i think you and yamanika should start dating that's my don't start rumors don't don't start you know she's looking for someone she's looking for someone to land on and it might just be you It might just be you, Roy. I love Yamanika, and I've told her a long time ago, I don't know if you stepmom material.
Starting point is 01:10:08 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, how do you see, what's your view or long lens of our current political situation? How do you see things?
Starting point is 01:10:30 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.
Starting point is 01:11:31 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.
Starting point is 01:11:52 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.
Starting point is 01:12:13 And who needs straight men anyway? Thank you, Roy. Wait a minute now. And on that note, 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 penurious miser declined to put a coin in the salvation army bucket penurious i just announced all my tour dates it's called the high and mighty tour i will be touring from February through June. So go get your tickets now. If you want good seats and you
Starting point is 01:12:57 want to come see me perform, I will be on the high and mighty tour. Do you want advice from Chelsea? Write into DearChelseaPodcast at gmail.com. Find full video episodes of Dear Chelsea on YouTube by searching at Dear Chelsea Pod. Dear Chelsea is edited and engineered by Brad Dickert, executive producer Catherine Law. And be sure to check out our merch at ChelseaHandler.com. i survived nine months in captivity and i've spent my life exploring how other people survive what should have destroyed them i'm elizabeth smart and these are the survivor files every week i'm with survivors who live through the unthinkable abducted stalked controlled and nearly silenced these are stories about what it takes to make it out alive listen to the survivor
Starting point is 01:13:50 Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. Each week, we're connecting the dots between books, the internet, and pop culture with your favorite writers book talk creators and plenty of overthought opinions listen to pro society on the iheart radio app apple podcasts or wherever you get your podcasts did you hear the new episode of the hey jonas podcast we are at d23 so we'll see who stops by the cast of frozen stopped by
Starting point is 01:14:35 kristin bell josh gad and adina menzel i auditioned for frozen what for kristoff they said okay what are you going to be singing today i said i don't know that must have been why you didn't get it Plus, John Stamos, Hayden Christensen from Star Wars, and more. And I guess I can share that, uh... No way. Listen to the latest episode of Hey Jonas on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey, this is Hayes Davenport.
Starting point is 01:15:02 And Sean Clements. We host the podcast Hollywood Handbook. Each week, we talk to someone in show business and try to help them with their careers and see what they have to offer us. Everyone has a good time, and no one gets mad at their publicist for letting them do our show. We've had a lot of great guests like Sarah Sherman, Adam Scott, Danny McBride, Ben Stiller,
Starting point is 01:15:20 and a lot of other big shots that wouldn't be where they are without us. Listen to Hollywood Handbook on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. On the new podcast, Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle.
Starting point is 01:15:41 I chose option B. I'm Julie Pinheiro, and I travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word solita, trading the pity for possibility. Listen to Solita on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is an iHeart Podcast. Guaranteed human.

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