Chelsea Handler (Chelsea Lately, Chelsea Handler: Revolution) joins Brooke for the final episode of season one! The two chat about the surprising way Chelsea got into comedy, their cringeworthy Bill Cosby stories, and how the death of Chelsea’s oldest brother changed the entire course of her life. Plus, Chelsea looks back at her year of “Now What?” moments, including fighting to get her special sold and deciding to walk away from her relationship with comedian Jo Koy.
What do you do in life doesn't go according to plan? That moment you lose a job, or a loved one, or even a piece of yourself. I'm Brookshields and this is now What, a podcast about pivotal moments as told by people who lived them. Each week, I sit down with a guest to talk about the times they were knocked off course and what they did to move forward. Some stories are funny, others are cut wrenching, but all are unapologetically human and remind us that every success and every setback is accompanied by a choice, and that choice answers one question. Now, what what drug do you think I could use? Because I'm the worst drug like, I can't. I don't think you should take any drugs. I just feel like you want to, but I can't know. I don't think you should. I don't think it's for everybody. I thought you'd have this great answer for me. No. No, But when I'm in New York next time, you and I are going to go for a drink and I'll give you a proper assessment. But I can just tell I think your personality, certain personalities don't react well to drugs, and I feel like years might be one of those. I'm literally the first time I ever smoke thought. It was with Judd Nelson and we went to go see Dry White Season, and first of all, it was a bomb which I did not know how to use. I literally tried to Oh, I'll try to get my mouth around the whole. I think that faces so stupid. Bro Oh my god, Oh my god. I was like, I've never seen one of these. He's a mouth in it in it. Anyway, we get to Dry White Season and it's a packed theater and I'm sitting there. All of a sudden, I start going and he was like, never again, never again. Well, I smoke you doing any Any real drug user does not want to be around a newcomer. My next guest needs no introduction, but I'm going to try. Chelsea Handler is a comedian, a writer, a producer, a fellow podcaster. She's many things. We first met when I was a guest on her late night show, and I just loved how comfortable and fun she made that experience. Since then, Chelsea has done a lot. She's had done so many things, including her latest comedy special, Revolution, which is out now on Netflix. She's just a fabulous guest and we had a blast catching up. I am grateful to her for sharing her incredible story and for being so open, And I hope you all enjoy this interview as much as I did. So here is Chelsea Handler. I thought that I was busy. I mean I really I was like, I'm doing so many I'm so busy. You are superhuman in what you do. It's amazing to me. You've written what six best selling books, You've gotten numbers of specials Netflix, HBO, You've hosted countless shows. I've been on your show. How do you have the energy to keep keep going at this level in this pace? It's so unbelievable. I don't know. It's funny, you know when people say you're so busy, how do you do it all? I'm like, I feel like a lazy person a lot, you know, Like I could easily get into bed either reading a book or watching TV for close to six hours if you if I had my druthers, that's my happy time. I've been on tour for a pretty like almost eighteen months, um, and that that is exhausting just because of the sheer, you know, just the travel, and so that can kind of be you know, that can kind of really wear you down. Um, But I just find that if I keep myself busy with lots of different projects, that I have the most amount of energy because my interest peaks when when it's constantly jutting back and forth. I think when I focus on one thing alone is when I start to get bored. But it's hard to get recognition for all that we do. And I don't know, do you feel like you get enough credit for how extraordinary your work ethic is and what you produce. Um. You know, it's funny. I have a new special coming out and I paid for it myself, and I remember having going out and selling it and it was challenging. There was a lot of interest, but everyone's like, we can't afford her. You know, our budgets are all contracting, we're heading into a recession. We don't want to insult her with a lesser offer than she's used to And I was like what, I was like, well, wait a second. I just put together the best special, in my opinion, I've ever done, and I had a hard time getting what I you know, well, eventually it all worked out. It worked out. Netflix stood up to the table paid me. But it was there was a period of time where I just thought, what if I'm not doing the right thing, Like, am I supposed to even be doing this? Like, of course there's ego involved, because we're all all professional and we all want to get recognized for the work that we do, especially when the work is top notch. So it was just another one of those examples which I've gone through before in my life professionally, where you think the bottom is falling out and then you find out, oh wait, okay, there was just an energetic shift or whatever. The stars weren't aligning, and then they did. So Yes, I definitely have periods where I'm like, I don't feel recognized, and then I have great periods where I feel totally validated and recognized. How long did it take you to write the upcoming special? I'm curious about that process, um, I wrote that. I mean, I've done about probably a hundred and forty shows. I literally started the show and I had eight pages typed out of material because it's so hard to put it down to memory, so you have to just keep doing it, doing it, doing it, and then it clicks. So I would say it took me about three months to get really like get it, and then once I got it, then you're just practicing the new wants, the delivery, when to pause, when to play? Do you practice in front of people or do you practice just in front of the director or no, I just do you just do shows? You just do them over and over, you go on tour, and you would repeat it. I don't think I've ever done stand up for myself in the mirror or for one more. I don't think you can otherwise it's not stand up, no, no, I would be sit down. You do it with such ease, like there's no angst. It's almost as if it's all just coming up off the top of your head. And to me, that's a huge talent. Oh well, thank you. Well, I think my talent is storytelling. Those are my books. That's my personality. I just have stories that I like to share, self deprecating and showing everybody that they're not alone anyone who has a similar experience to you. Making it clear that anyone who has any experience doesn't understand that there are millions of other people that can relate to that. So whenever you're in a situation where you're grieving or you feel so alone, are isolated. It's so important to remember that people have been through what you've been through. You're never the only person that's been through something. Can I ask you how that I'm so excited about the new Netflix special? Um, how is it different than your past? It's, uh, well, it's a it's I don't know. I'm just I'm much more. I'm so I have so much more clarity and I'm just like so much more of a professional now that it's just sharp sharp, it's funny, it's poignant, and it's a story. It's a love story. It's about me kind of losing my faith in men and then kind of all the examples of why and then finally meeting Joe Koy and renewing my faith in men, and and then even you know, after that not working out, not to shut down and close off, to not use a failed relationship or a relationship that didn't go the distances as a reason to to say fuck it, I'm single again. Like I'm not doing that. I do want a relationship. I'm it's okay for me to admit that now, Like I've learned and I've grown so much that I got a taste of what that togetherness feels like and I wanted again. So it's a real kind of like it's it's kind of like a love story for yourself actually, yeah, and for others, you know, for inspiration for other women who you don't ever have to settle. You just do not ever have to settle. You have to have your standards at a certain level and somebody will meet you there and that will happen. Did you have comedy, Like, who are the comics that you liked? Oh? Bill Cosby? So there you know that was my favorite? Uh that was a big whoopsie doodle. He actually once I was in Atlantic City and he and I were both performing, and he called me, summoned me to his hotel room. This was probably fifteen years ago, and luckily I was with a crew of like four guys, um my opener, my two tour manager, blah blah blah, a videographer whatever. They were all men, and so I brought them with me to Bill Cosby's hotel room. And he was so pissed, she said, who are these guys. I'm like, well, that's my opener, this is my videographer, this is and he's like, you're opening for a woman, That's what you're doing to the guy opening for me, And I was like, what's your problem? Come to find out, his problem was that he couldn't roofing me when I had four guys there. God, I we uh. Suddenly Susan premiered and for that one night in history, we got better ratings than his show, right. I mean it was because it was probably people thought it was going to be a train wreck, right, and nothing to do with anything truthful about it. And he called me in my dressing room and I got brought off stoff the stage too, into my dressing room, and I thought he was going to congratulate me and sort of take me under his wing. And I got on the phone and I said, oh, yes, Mr Cosby, and he said get off TV. And I was, I mean I was, I thought he was kidding and and but there was something so serious about it. And I said, oh, I don't know too, I'm just here, but I have a contract, and and you know, I was like so crushed. I love I love the idea to Marritie like he thinks he's gonna say that to you and you're gonna just quit your job. And then he hit it into well, you know what you're gonna need better writing, so you've got to stand up for yourself and get better writers. And I was like, really that was passive aggressive, like thank you, thank you, Like, do you have a roofy I could borrow so I can give it to you. Did you always want to be a comedian? No? I only became a comedian because I was out of ideas and I wasn't going to get an acting job because my acting is questionable. Well it was like auditioning. I just wasn't good at auditioning when I'm actually honest that doing. Yeah, yeah, totally. And then I was in a d u I class. I got a DUI when I was twenty one, and I went to this du I class where you have to like get up and tell your d u I story. And I was so scared. They were like twenty five people in the class and everyone had to get up and tell their du I story and I was like, oh, I couldn't publicly speak. Was just so scared. And then finally, on the very last day of the class, they called me and I had to get up and tell my d u I story in front of the whole class. And my d u I story is pretty funny because I got in a fight with a cop calling him racist. Meanwhile we were both white, and I I just I spent twenty four hours in sybil Brand attention facility like this women's prison in l A. Like it was a hot mass situation. I couldn't get released because the systems went down, so I was actually in there for way longer than I normally would have been for a d u I. But anyway, I got up, I told my story and everyone in the class was just howling and dying with laughter because my story was so silly. And I remember the guy that ran the class came up and was like, this isn't a stand up comedy club like this, you're wilking this, Like now you have to get off stage. And then when I got off stage, everyone's like, you need to do stand up comedy And I had never thought about it. So I have to credit my d u I with getting me into stand up because the next week I went to the laugh Factory or the Improv and I did an open mic and then I was hooked. Were you always that kid in your family, the jokester or the one that performed or did that develop later? I mean, yeah, I was always just like I mean, I was born and I was four years old, I asked my father if he had a dowry for me because I looked at the financial situation and I was like, this does not add up. I'm like, you guys have six kids, what's your game plan for finances? Do you even have a savings account? And your dad was a German immigrant my mom my mom was a German mom. My dad was a Jew. So my mom was a Nazi and my father was Jewish. So that was a big dynamic, a couple of boxes. Yes, absolutely, And you're child how would you describe your childhood like? Um? Like chaotic? You know, we had a lot of love. I mean, my siblings and I are really tight. Um. Our brother died when we were not when when I was nine. He was the oldest. I was the youngest. So that was traumatizing and we didn't really have the skill set to deal with that. So and our parents were pretty clueless. You know, We've always been pretty tight ennit. We always stick together and we're always there for each other. My sister just got spinal surgery a couple of weeks ago, and I went up there for two weeks to help, you know, play nurse. And my whole family is like Chelsea, like, are you really the right person to go up there? Like you're not that good at that? And I was like, oh, watch me. I was like, listen if when it's probably the best at it, because they're not going to be grossed out, you're gonna kind of just cut to the chase and help her exactly. And she has this long, long, like this wound where they went in um down her back that was so gnarly that I was like, oh that I had to clean every day. And my sister got looked at me one day and she's like, I just can't believe you, Like you're just the best nurse in the whole world. I would never have expected this. And I was like, exactly, I'm fucking reliable. I'm reliable because my parents were so unreliable that it's so important for me to show up for people when they're in need. Would you say when your brother died that was the sort of the first and most significant, now what moment in your life? Yeah, be going to therapy was probably the most significant part of my life. In addition to that, because that helped him that was later, right, that was when I was like forty. But to be able to unpack it and have and and gain a self awareness about why my behaviors were a certain way and why I acted a certain way, that was a big, huge moment for me. And it took about a you know, it took few years to like absorb all the information that you learn in therapy, absorb about because you you learn it and then you have to apply it to your life and then you don't want to lose the good parts of yourself. So it's a very interesting dance. After you do deep analysis, you're like, okay, now now what No, No, it's hard to know who you really are anyway if if who you aren't that day has been defined by exactly exactly, So you're like, well, who would I be if my brother it and die? Would I even be like a celebrity? Would I have been driven to get this much attention? Would I have been interested in getting myself to be you know, seen and known and heard? I mean, I wonder you know, and I was a nine year old though, how did you did you have any form of processing this huge loss at nine? Oh? No, not at all? I mean I just remember seeing my mom and my dad fall apart at the seams. Because I was their firstborn. I had never seen my father cry. I mean, we all just kind of went to our respective corners and grieved, and you know, in Judaism we said Shiva. And there are people coming to our house all week long with roast beef and corn beef and pastronomy. And I remember watching all of these Jewish people eat pastronomy sandwiches, thinking what, what kind of fucking morning is this? This is so weird. And I remember my learning that my mother wasn't Jewish. I had thought my mom was Jewish my whole life until I was nine. And then I remember because they were talking about burying my brother with my rabbi and they were like, well, we can't bury we can't buy a plot in a Jewish cemetery, and let's read a converts reading my mother. And I was like converts. I'm like, is a mom Jewish? And my Dad's like, no, mom's Mormon. We'll talk about that later. And I was like, what's Mormon? And then I read the Book of Mormon and I was like, Okay, I'm this is ridiculous. I'm like I'll obviously stay, I'll be Jewish. But I was bought Mitzvah and I was raised Jewish, like I went to Hebrew School, Like I am a Jew, I don't really practice Judaism. I'm not that into any religion quite frankly, but it's the one religion I actually identify with if I had to choose one as being a Jew. Every time I go to from the time I was a little girl go to Abot Mitzvah or a bar Mitzvah, I always asked my mother if we could convert. Always did. I said to my mom and my mom, this feels much better than than all of the stuff that we that we learned, and Catholicism, and and I feel good about myself in this environment, I don't feel good about myself. And you know, getting ship every single day, a shamed and then the confession and the I mean, my whole life was built around being guilty and and confessing. And um, do you think you grew up too fast? I wouldn't say too fast, but I grew up pretty quickly. Like I I remember taking a plane ride, my very first plane ride with my mom and like two of my brothers to Los Angeles from New Jersey. I had never been on a plane. We walked back to the first class section and I was like, who are these people? Like these are my people? And my Mom's like, oh no, honey, we're we have six children in our family were never flying first class. That is not something we can ever afford. And I looked at her and I was like, speak for yourself, bitch, you know. And I came home. I was ten years old. But when I was ten, I looked like I was fifteen. I started my own babysitting company where I was babysitting for kids that were older than me. I had a fourteen year old client who I babysat for the entire summer when I was ten. And when I came back from that trip, I had thirty dollar saved. And the next time we flew to California, I was thirteen years old and I bought a first class ticket through a travel agent that lived down the street from us. And when we got on that plane, I saw my seat to a I was like, I sat down. I'm like, I'll see you guys at the end of the flight. And my mom was like, what are you talking about? This isn't funny. I'm like, no, it's not funny. If you think I'm flying coach, you're wrong. These are my people. Wow, that's kind of incredible. Were you the only one in your family there's six of you that sort of had that independent Well, we're all pretty independent. But I definitely had like my sight set on a bigger life, Like I didn't want to be dependent on my on a man. My father and my mother's dynamic was not acceptable to me. And I also felt like betrayed by my brother when he died, and I felt abandoned by my father after my brother died because of the way my my father fell apart after that, it was almost like he had no other children, you know. So I definitely had this thing about like not trusting men and not wanting to be dependent on men, And you know, that was another thing I had to unpack during therapy, Like I was so closed off to relationships because I'd have these stupid judge mental barriers, like you know, if somebody wore an air May's belt, it was over. If somebody if I saw a man in flip flop, so that was over. Or if I saw a pinky ring, I'm like, oh my god, boner killer, no way can I have sex with this person. And I had all of these like silly materialistic barriers to protect and preserve my independence in my safety. And only through therapy did I understand that, you know, that that what that was about, and how to let it down, like you know, let it break away so that I could be in relationships with men and not have you know, crazy expectations. When did boys sort of come into the picture as boyfriends? Oh early, I was like I was getting I was sexually active when I was like thirteen, fourteen years old, Like I had a lot Mom talked to you about it. Didn't know anybody want to talk to me about anything, you know. My parents were just so ill equipped at that. I mean when I got my period, like no one had told me about that either. So I mean my sister brought me a Maxi patch, like okay, here you can put this in, and she's like, or this is a tampon. I'm like a maxipad. You want me to put a Maxi pad in my underwear and then just walk around with blood floating in there. I'm like close, I'm like, give me the tampon. But yeah, I I didn't know about sex. I was very promiscuous when I was a teenager. It was like validation, you know, like I just wanted to prove that I was special and that boys liked me. I, for one, and have always known that I wanted children. It was probably the first thing I knew for sure. You've talked a lot about not wanting children, and I think that's very important because it normalizes an experience and a feeling that many women have, but they are shamed by others when they try to express it. What's been the reaction of other women when they know that piece of you? Well, I think it's I think the reason why I'm so loud about it is because of the reaction from women who feel like, oh my god, I don't have that feeling. I don't have that that biological clock ticking. I don't feel that way, you know. Um. And so I like to give voice to all of those people, because that isn't a defining thing. I mean, it can be, but it's not the only way to define yourself, and it's not right for everybody. And I really think if you want to have a baby, you really have to want a baby, like the way that you're talking about it not be like, um, forty, maybe I should have a baby because it's gonna be too late if I don't do it now. It's like no, no, no, no, no, that's not the reason to have a baby. You know. I think I think that there's so many women who are thankful that you're sort of destigmatizing it. Well, listen, I'll tell you, you know, watching your Instagram and watching your relationship with your daughters and Chris and uh like, I am always like, that's somebody who wants you know what I mean, that's somebody who wanted to be a parent. And that's very refreshing to see as well. Like it's so obvious when parents are just so in love with their children, and it's nice to see. And that happens all across the board. It doesn't. It's it's whether it's life or it not just being a mother. And I really, you know, I really just I admire that endlessly of you because you're you're you're curious, but you're also so so honest, and I I struggle with this, so I'm asking you, do you are there parts of yourself that you don't share? M that's a good question parts of myself that I don't share. I'm sure. I mean, I try and be mindful of the people that are in my life that don't want the exposure that I bring to the table. Like you know, I mean, except for my family, they're just fucked no matter what, because I'll just kind of constantly drag them whatever is happening. Do you have nieces and nephews and with within your Oh, I'm I have eight of them, and I you know, I I talked to all eight of them all the time, and that's my role. Like, I love being an aunt. I'm cool. I provide edibles. I provide you know what I mean, Like I take them on safari. I I'm like, I want my relationship. And you know, listen, if I had my own kids, I wouldn't be available for that dynamic. And I'm able to do that with strangers, you know, kids I'll never meet. I've been able to send to school or do nice things for so I feel like, you know, that's another advantage, you know, for the women out there that don't feel compelled to have a child, there's so much you can contribute without having them to other children. When I look back, I mean That's why I really wanted to do this show. It's because I'm so fascinated by people's now what moments, whether whatever it is at the time, where there are other now what moments past that first, very very important one, Yeah, I had. I have had a few big ones, like when I left my Netflix show. That was a pretty seminal moment in my life because I was so upset about Trump being president, so upset, and that's when I decided to go into therapy. And when I really was, you know, unraveling what the pain of losing my brother was and that that lack of control and you know when the rug gets slipped, you know, pulled out from underneath you, which is basically how I was equating the Trump residency, like wait, wait, wait, this wasn't supposed to happen. Now what where? How do we handle this? And then I think another seminal moment for me or a now what moment for me? Was, um, you know my last relationship. I was dating this comedian that I had known for years and years and we kind of reconnected and we dated for about, uh like eleven months, and I really believed that this was my guy, Like I thought, oh, my God, I won like I got everything. I have my career, I have respect, I have I have my family, I have so many friends, I have all of these things. And then I thought this was going to be the person I spent my life with. You always said you were not the marrying kind, so change. Yes, I'm not that hard up to get married. But I was open to the idea of it, and we definitely discussed it at length because it was important to him. Um. And then you know, towards the end of the relationship, it just became clear that this was not my person. What happened? Do you think, Like, I mean, I just discovered some stuff that I mean not discovered. There was just some behaviors that I that we couldn't agree on, and I was like I would It was a It felt to me like I would have to abandon myself, which maybe I would have been okay to do if I were twenty or twenty five, but I wasn't willing to do that. No matter how much I loved this person, and I loved him so much, I was not going to abandon myself. I was like, I'm not going to change this behavior. I'm not going to change the way that I behave in order to make you feel more comfortable. I'm not doing that. And I had to walk away from something that I really believed was going to be forever relationship, and so that was difficult. But that's brave by the same token. I mean, did you think you were being brave? Yeah, I mean I wasn't. I was in a lot of pain, but I I just it was unacceptable, Like I just I said, this is you can't, this can't happen. Our relationship just evolved and we both could not agree on a situation or several situations, and I thought, you know, therapy could help, but did not, and I exhausted any avenue I could think of, and then I just realized this is futile. And yet he directed the current. Yes, yes, he directed. Was this after you broke I was right before we broke up? Because you do seem to have like a superpower of staying friendly or at least of coming back to being friends with your exes. I don't know. I wouldn't say I'm good at that. I mean I am now like as a you know, after therapy, I understand like there's no reason to be angry at anybody when something doesn't work out. You just have to understand things don't work out sometimes and there's no reason to have vitriol about it. But yeah, walking away from him was was one of the most difficult things that I've ever had to do. Are you still in contact with each other. I haven't spoken to him in a while. No, But I just, uh, I mean, there has to be some accountability, you know what I mean, like from him for about what happened, because it was just ridiculous and uh, you know, and we I don't think we can have a friendship until there's some accountability and some responsibility taken. Do you think that you know more clearly now what you're looking for in a relationship. Yes, I need somebody a who reads books and reads the news and cares about global affairs. That that is a major which I never thought was like the most important thing. But I'm so about that And it's not fun to be to reading the paper and not be able to discuss that with someone. Like a thirst for knowledge, a thirst for growth. You know, there's nothing I remember I dated this guy once and I walked out. I came home one day he was visiting me, and I walked outside into my backyard and he was just reading this Bell Hooks book and I remember going, oh my god, this is the hottest thing I've seen ever. Like, I fucking love when men read and then they read about women. I get it, I do, I do understand. I mean, I think I spent so long kind of making that list together of those things that I wanted the person to be, you know. I mean, I'm my first husband was someone who didn't want to do any of that, and it was a place of insecurity for for him, you know. And well, listen, there's more to the world than your career. A like, my career has always been the most prominent part about my life because I'm not married and I don't have kids, But it's definitely not all of my life. I have such a thirst for knowledge and for travel and for making sure that this is not the only definition of me. And has your stand up changed you think over the years? Has your stand up consistently changed? Yeah? I mean I used to be a little bit like sloppier. I get drunk and do a special I didn't give a ship. I was just so like I was so I had so many candles burning at as so many you know, at every end possible that I just didn't care as much about you know, the integrity of the work wasn't at the level that it is now. And so now I you know, I've I've kind of come back to myself in a big way. I understand what my purpose is and that I have a very strong voice and to use it for good, not to just use it for personal gain. Which whoever, would you ever host another talk show? Yeah, I'm down. I mean, I'm in discussions to do that right now. So I mean I want, yeah, I want to return to that. You know, that's what we want you to return. We want you to return and I think that would be a great thing. Um, if you were to look back at your life, what would you save. A through line is honesty m M. Doesn't get better than that. You can't beat that. That was Chelsea Handler And if you want to hear more from her, go watch her latest comedy special Revolution. It's out now on Netflix. As for us and now what, we are going to take a break for a few weeks, but we'll be back early next year with a fresh batch of incredible episodes for you all. Happy New Year, Thank you for listening. Now What. Is produced by the wonderful Julia Weaver with help from Darby math Stirs. Our executive producer is Christina Everett. The show is mixed by Bohed Fraser and Christian Bowman. A special thanks to nicky Etre and Will Pearson.