On with Kara Swisher - Chelsea Handler on Men, Trump & Money (+ Excellent Parenting Advice)

Episode Date: March 13, 2025

From spiking her childhood lemonade stand drinks with vodka to launching Netflix's first talk show, Chelsea Handler has always had an entrepreneurial instinct. Case in point: the comedian’s new book, “I’ll Have What She’s Having” is her sixth to top the New York Times best-seller list.  Chelsea joined Kara onstage at SXSW to share her juiciest stories from the book (including the joke that made Woody Allen literally spit out his desert), offer her unfiltered takes on President Trump and Elon Musk, break down the problem with men, and reveal how she became a “father” to her ex-boyfriend’s three daughters. Questions? Comments? Email us at [e-mail] or find us on Bluesky, Instagram, and TikTok @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Hi, everyone from New York Magazine and the Vox Media Podcast Network. This is On with Kara Swisher and I'm Kara Swisher. My guest today is the comedian and seven-time bestselling author, Chelsea Handler. She has a new Netflix special titled, The The Feeling that comes out March 25th. And she recently released a new book called I'll Have What She's Having. It was published on her 50th birthday and fittingly it's a collection of essays that chronicle her journey to becoming the woman she always wanted to be or as she puts it, a beautiful hurricane.

I found the book very funny and full of really interesting lessons. I love talking to Chelsea, not just because she's hilarious, but she's also politically engaged and a savvy entrepreneur who's been very successful in streaming, podcasting, publishing and touring. I spoke to her last Sunday on the Vox Media podcast stage at South by Southwest and we got into all of it, her new book, Politics and the Business of Being Chelsea Handler. I also told her she needs to date Elon Musk in order to save us from this nightmare. She declined. Unsurprisingly, it was a great conversation, so stick around. Support for the show comes from Smartsheet.

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I'm jealous that I wasn't here for that. Yeah, she was great. She was great. I love Elizabeth Warren. Yeah, she's fantastic. So Chelsea, thanks for joining me in this conversation of Vox Media Podcast Stage at South by Southwest, presented by Smartsheet. Let's start with your book, which is number one on the New York Times

bestseller list. Wow. Why do you think that is? Why do you, you know, there's a lot of right wing books up there. There's a lot of stuff like that. Why? I know. But why do you think you got to number one? I don't know why I got to number one. I have a pretty good track record of getting to number one. Yeah. So this is my sixth number one New York Times bestseller.

Yeah. And thank you so much. Every time, I was just telling Kara backstage, it just never gets old to get that phone call that you're number one on the New York Times list. And I'm from a family of six children. I'm the only one who didn't go to college. So I love calling my brothers and sisters

and congratulating them on their wasted efforts in college and that I was right all along. I was the youngest of six and I would tell them, you guys stick with me, I will show you the way. I will take this family to the next level. And now they know that I was fucking right. That's right, that's right. Which you write about a lot in this book.

But you started the book with a quote, to have and not to give is worse than to steal. Why is that the quote? Because I really appreciate generosity, my own generosity, the generosity that my mother instilled in me. And I think the world obviously could use a lot more of it now. And it's very important to share everything you have, including your stage, your time, whatever you have to give, give it. And when you're done giving, are you sure that's all you have to give?

Because I can bet you, you can find more to give. And it's the world that we're living in, we need more of that. And I want generosity of spirit. I want to demonstrate it. I want to display it, and I want generosity of spirit. I want to demonstrate it. I want to display it and I want to spread it. Excellent. So you also dedicated the book to stewardesses and there's a great scene in the book. That's a very antiquated term, Kara. They're called flight attendants. Please get with

the program. I know you're flying around privately, but try and remember us small people, please. Flight attendants. Flight attendants. Flight attendants. Mostly women though, you did say, oh the guys. They're mostly women and then the men that are flight attendants are also our sisters. Okay, all right. So why did you dedicate it to them?

I spend a lot of my time on flights. I'm sure many of us in this room do. I spent about a... I'm going to say you wanted to from the early time you walked through first class and said, these are my people. Yeah, well I wanted to spend my time in first class from a very young early age. When I was on my first flight, I walked past the first class section.

I was like, I sniffed around. I was like, this seems like my group. And my mom was like, this is not our group. You will never be able to fly first class. We can't afford that. And I was like, speak for yourself. So anyway, I do fly a lot and for work, for whatever, I spend a lot of my time on planes.

I wrote half this book on planes and flight attendants have been through hell. People treat them terribly and they need our respect and they need our patience. They are stuck with us in the sky and we need to be nicer to them. And yeah, after COVID and all of those assholes. White lotus in the sky.

I mean, yeah, white lotus in the sky, right. You're stuck in a tube of disgusting air. Let's be sweet and generous and gracious to them, please. And you offered to beat people up. I will always be on a plane. I act as a flight attendant, yes. If there is a problem or a nuisance or someone needs to be removed, I'm your girl.

Yeah. One of the reviews was, a pleasingly unformulaic book of hard-won advice that never rings false. Do you like that review? Oh, I never heard it. Yeah, sure. Yeah. I love it. Are you pleasingly unformulaic?

I'm unformulaic, yeah. And if it's pleasing to you, that's your opinion. Yeah, I'm glad to be pleasing somebody. I just need to please a few people, not everybody. Who do you have to please? Just enough people to give me my career, you know? The fans, I want to please my fans, the people who've provided me with this life.

But I'm not looking to please people. I'm not a people pleaser. I want people, I want to spread joy and sunshine, but I'm not trying to please you. Right, I can see that. So, explain how trying to please you. Right. I can see that. So, explain how your father changed you. You've built a very deep and caring relationship with three girls whose dad you used to date.

We just talked about it backstage. They called you father, and you write that one of the girls said to you, father is always with us even when she's not. And you thought to yourself, this is the single best sentence I ever heard in my life. Yeah. Explain this story. I found it, I have a lot of kids, as you know. A lot of kids. And I was very upset by the story of you moving in there.

Not that you did, I felt good that you did, but these kids had been kind of left alone by their parents in a way. Yeah, their parents just kind of had kids and they were career people and they thought, well, these kids will be of the world. You know, like they were kind of two people with huge careers that also had children,

not people who had children who also had huge careers. Do you know what I mean? So the kids were kind of left by the wayside, and my ex-boyfriend and his relationship with his girls just hurt me. Like, it hurt my heart. And I'm from a family of three girls, three boys. And when I saw these girls, I recognized in them so many things I felt in my adolescent angst

and my, like, you know, the neglect and the needing to be seen and the feeling of being ignored and how that, like, I related to that feeling so much that I just wrapped these girls up and became for them whatever I could be, which was like an interim parent. And they call me dad.

Well, they call me father because they have a dad. So they call, I'm father and he's dad. He's very confused all the time. I was also very confused, but they are the huge loves in my life. They still are. And I shared that in the book because people think that I don't have children,

so I hate children. But you do have comedy about hating children. I mean, I wanna be child free. I'm very excited that I've remained that way and that I've remained single for as long as I've had. Like, I feel like now I'm free. I got out of that tunnel where those things could have happened. Like, I could have had a baby or gotten married, and I didn't.

And now I feel like I'm 50, and I have the whole world ahead of me. Like, I've never been more excited to get through a test, you know? But these girls are very important people in my lives and they are my children. I think of them, you know, I would do anything for them. So yes, it was important for me to share that because whenever I'm writing books,

I'm like, what if, I'm so candid about my life. I'm not precious about my personal life or anything. I never want to be that way. And I'm not very private. So I'm like, what can I share that I haven't shared? And I was like, oh, that was, that's something that people don't really know about how many children are in my life

and how many children I really do care for and have in my- Like your nieces and nephews. Well, my nieces and nephews are one thing. They're related to me, but so many people outside that are not related to me whose lives I'm able to make big contributions to because I am single and because I am child

free. I have the bandwidth to help even more people than I would probably help if I only had my own family. And that's something that people don't talk about. When you are child free, it opens you up to really be helping the world in a bigger way. You can make other contributions. Your value comes from a multitude of things, not just being a mother or a wife. There are many other ways to contribute.

So I'm glad so many women are having honest conversations about procreating and that it's not for everybody because it's fucking not. You know, some people aren't good at that. So it's good to know. You seem to be good. I'm good at helping out. Right. You know, I'm good at being a big sister and helping push and making sure, picking people

up. But I don't need to be a parent. Any dog of mine will tell you. You seem like an excellent dog owner. Well, I mean, I have an excellent system in place. I'm not the best dog owner. I'm not the one doing all of the things. And it's even for a dog.

So imagine how I would show up for a real person. You do wear them on your back. Yeah, I ski with them when I need to in my bikini for my birthdays every year. So they're good for that. Where did you ski this year for that? Where did you do this? I did that on Soldier Mountain in Idaho this year

with like 25 women. I was like, get me 25 50 year old women and let's all ski together. So we took a little LSD and we all skied. Yeah, yeah. In bikinis? In bikinis all skied. Yeah, yeah. In bikinis. In bikinis, bathing suits, yes, yes. It was very joyful. Was it? Yeah, it sounds like it.

Yeah, absolutely. I noticed you didn't invite me. It's very exhilarating walking. I can ski. You can ski? Yeah, I'm not skiing in a bikini. Why not? It's not for me, it's not.

We're doing it in Palisades Tahoe Friday. We're doing it for Gold Bond. We're doing a ski event that was inspired by my birthday videos. We're gonna break the Guinness Book of World Records in Palisades Taho Friday, March 14th. And anyone can sign up. Men, women, snowboarders, skiers. We're doing it. In bikinis? In bathing suits.

Oh, good. That's great. Any bathing suit you want. Any bathing suit. Oh, interesting. Okay. Now, so one of the things you said the book is about female sisterhood togetherness. Let's stick together and be empowered by others. And you write, the admonishment and disdain that comes in response to women's relationship with herself is a great reflection of how slow and unchanging our society is. Talk about that a little bit.

You say what you want, you talk about loving drugs and alcohol, you ski topless, you never want to get married and have kids. You're essentially JD Vance's nightmare. Talk a little bit about what you're talking about here, the greatest reflection of how slow and unchanging society is. It's just like men are upset that women don't, I mean those types of men, I understand there are my type of men that understand why we would make that decision, but those types of men that want to keep women at home and being mothers and not having,

that's just so antiquated and it's so slow and it's so boring, we're so bored. I think the political situation we're in is a direct reflection of the fact that men are so scared of women. Why are you acting like this if they're not? Why would you overturn Roe v. Wade after the Me Too movement?

That was a direct correlation in my opinion. I think that, and women aren't going anywhere, and men, the men that stand with us aren't going anywhere. So this is a blip of really unfortunate history in our country. I can't believe we've had to go through, we're gonna have to go through this for a second time, and probably worse.

But I don't have any hope lost about the success of women and the contribution. Women are more powerful and more independent than we've ever been, and that isn't going to change. What do you think of, you know, my other podcast partner, Scott talks about the crisis of young men and men right now. Do you think they're in a crisis or do you think about it at all? I do. I was on a plane yesterday with a really young,

I think there's a new generation of young, this boy, he was on this plane, this 16 year old boy, and he asked if he could put tiger balm on his knee if the smell would bother any of us. And I was like, I wanna have sex with you. Like, I know, I'm not having sex with a 16 year old, but you know what I'm saying, when he was older, and when he gets older, maybe I do want to have sex with him.

But that was just a nice indication of how conscientious, and I'm noticing young men like that when I'm talking to my friends' children, like they're very engaging and they're more confident and they're smarter than when we grew up. So I feel like this new generation, they're very, they're, you know, woke in the right way. They're not, it's not a cancerous woke where everyone's like, it's conscientious and they're compassionate you know, woke in the right way. They're not, it's not a cancerous woke

where everyone's like, it's conscientious and they're compassionate and they, and so I'm very hopeful about our young people. I think they're, they're a lot smarter than we're giving them credit for. Agreed. Do you, what do you attribute attraction to Trump though, with a lot of young voters?

I don't understand the attraction to Trump with a lot of young voters. I don't know if that is the, I mean, I can't speak to that. I can only speak to the fact that we're gonna see, how this all shakes out. People aren't going to be pleased with this when the next midterms come around.

No one, Trump is not out for anybody, but rich people as we all know. So it's like everyone who voted for him in the hopes of something else, or some aspirational hope of a better life, a better economy, you know, they're wrong. That's not going to happen. The opposite is going to happen. You know, the people who don't have money are going to suffer even more. And so, you know, I don't know how to answer why anyone votes for Donald Trump.

I don't get it. So a lot of people did. Well, one of them was the idea of a better life, right? That the prices would be better, that there's more opportunity, and even though the economy was good, they didn't feel it. Yeah, but also any economist will tell you that you're finding an economy, an economy hits like four to eight years after the first president. Biden was working off of Trump's economy and Trump is working off of Biden's economy, but people are so stupid.

They don't even understand that. I don't get it. It's so obvious. You don't implement things into the economy and it has an impact right away to the stock market. It does, but not to the economy. You know, those are, I mean, some things, but a lot of things take a lot longer. Talk a little bit about money because the tax cuts will help people like yourself, right?

Yeah, I don't need the help. I'm happy to give my money to the people that need it. When you talk in the book about your parents as a financial hurricane and earning money is important to you and you've done well all throughout your career in that way, when did you first realize the importance of understanding money for yourself? Because you discuss it in the book quite a bit. I mean, I don't know if I understand money, but it's nice to have. It helps, you know, it helps a lot.

It's nice to be able to help other people with it. It's nice to be able to live a life that, you know, affords me the possibilities to see the world. Of course, I want to have a nice life. I like money, but seeing my parents struggle financially, we weren't poor, but we weren't wealthy. And there were like phone bills would be, phones would be turned off, things like that,

made me feel very insecure. And I definitely felt from a very young age that I wanted financial independence and I never wanted to rely on a man or a partner for that. Now I wouldn't mind a little help, come and gleg some funds. I support a lot of people, so I'm like, can I get some, I'd like a double family income, but that's hard to do if I don't want to get married. So I take the responsibilities on and then I have to hustle.

I told her to take one from the team and date Elon Musk and bring him back. Yeah, I'm not that much of a teammate. I don't think I can do it. I mean, there's a lot I would do for this country, but having sex with Elon Musk is not one of them. I can't. I can't.

It's just an idea. I would do so many other things though, you know, for the country. Such as? I mean, I can't think of anything. You're the interviewer. You have to figure out what I'll say yes to and what I'll say no to, Kara. Well, I think that's a good idea. But I mean, Elon Musk is just one that is above my pay grade.

Okay. He has a lot of money. I know, but that's not, I can't. Yeah. Yeah. But you should try it. You do it. Why don't you do it, Kara? Does anyone here want to do it? No. Yeah. Okay. All right. Wow. But you should try it.

You do it. Why don't you do it, Kara? Does anyone here want to do it? No. No. Wow. That's amazing. All right.

So one of the things though that in the book, you were very ambitious from an early age. I love the scenes of you. Very vicious? No, no, no. Ambitious. Ambitious, yes. Yes. Somewhat vicious because you cut your sister or your brother off working for you on a lemonade.

My sister, I fired her. I opened a lemonade stand. My sister wanted to partner with me on it. And then I realized pretty quickly, lemonade was not going to be a big profit margin. So I opened up a hard lemonade stand serving alcohol to the parents of the children and then children who were 10. They could also get a drink. And then I made a lot of money.

And then I had to cut, I had to lean out my staff. So I cut my sister, and then I got, I hired another 10-year-old named Nelson, and he was my bar back, he made the drinks. And in the first week we were 10 years old, we made $359 at our hard lemonade stand, and I gave Nelson his commission, which was $3.59.

And Nelson thought he had hit the jackpot. He's like, oh my God, I said, stick with me, brother. I will show you the way. I haven't seen Nelson since that lemonade stand, but I do now with my book, in conjunction with my book, I partnered with this brand Owls Brew and I made my own Chelsea Handler's vodka lemonade. We have three flavors and it's so delicious.

So my dreams all came true. So you're still in the business. So I'm still in the lemonade business, yes. Support for this show comes from Smartsheet. Do you ever wonder how many times a day you toggle between different screens, applications, and windows on your computer? Maybe 20 times? Okay, maybe 50 on a bad day? Try 1,200 times a day.

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for spaces, dental offices, and beyond that embrace sensory inclusion. Because true inclusion requires action with environments where everyone feels safe. Watch Sensory Overload now streaming on Hulu. So where does that entrepreneurial drive come from? Because you have been very entrepreneurial as a career compared to a lot of people. Yes, I'm very, I have a lot of authorship over what I do. I don't really like answering to people.

And I've managed to carve out a career where I don't have to answer to a lot of people. Even when I did really have to answer to people when I worked at companies, I didn't, you know what I mean? Yeah. Oh, I know. Yeah, I'm aware. And everyone is aware of that. So no, I'm aware. I'm the I mean? Yeah, oh I know. Yeah, so and everyone is aware of that. No, I'm aware. I'm the same one.

Oh yeah, okay, good. I thought you were talking about everyone knew about me. I'm like, I guess they probably did. But no, I'm good at being my own manager. I mean, I have my podcast, I have my books, I tour my standup, I have my residency in Vegas. I do everything the way I want to do it. I'm going on a European tour this year, like my first in years, you know, once the election

was announced, I'm like, I guess I'll go to Europe and spend some time apologizing to our allies, our European allies who we love so much. Thank you for your support over all this time. So I'm going to go to, you know, some public service work over there. And yeah, I'm very in Canada to some public service work over there. And yeah, I'm very... In Canada. In Canada. I have a house in Canada, yes.

That's a backup plan. Once we become the 51st state, I don't know what kind of plan that is. But yes, I'm very ambitious. I've always wanted to have a big full life and I feel like I am having one. How do you decide when to not do things? When to stop doing them? Well, if I'm just doing something for a paycheck and I don't feel any sort of creative stimulation,

I don't do it. I learned that lesson a long time ago, not to just take money because it's offered to you. You have to be a little bit discerning about what kind of, what you wanna put out there. And I'm reliable in the sense that I'm always elevating myself and there's an evolution. It's not just the same shtick over and over again. It's a more

evolved shtick. And I'm growing up. I'm 50 years old now. So I have different things to say. And my ambition is different. I'm on solid ground. I've been around the block so many times. I know myself. I know what I'm capable of. I know what my strengths are. and I'm not shy, and I'm not apologizing about any of it anymore, and I'm not trying to people please. I don't get caught up in other people's opinions, and yeah, you can say I've always been like that, but I really feel like that now. I'm impressed with me now. So that's all I need. That's true. But one of the things you've been, as you've been successful, you felt like you weren't grounded and you were going to therapy in the book, but you lost

confidence and you were second guessing yourself. You talk about this and you had a panic attack. Tell us the story of how you realized therapy had become part of the problem. Therapy didn't, it wasn't, it didn't become part of the problem. It just is so, when you go to therapy, it's so ironic because to get, I went to therapy to get my head out of my ass. I felt too self-involved and self-absorbed. But then you go to therapy and you have to spend hours

ad infinitum talking about yourself. So it's kind of hard to get away from yourself when you're, but that is the process to understand and gain some self-awareness and reflection and understand why you do the things you do? It's not the most pleasant process for anyone here who hasn't been to therapy. I'm assuming many of you have and you understand what I mean, that it's dirty.

You find out ugly truths about yourself and it's up to you to decide if you want to step it up and level it up and become the better version, the 2.0 version of yourself. And I did want that. I wanted to learn and grow and be stronger and more compassionate and patient with idiots. I wanna be patient. When somebody's stupid, I wanna be nice to them. I don't wanna go, why are you so fucking stupid?

You know what I mean? I wanted to learn that and I have learned it. Now I'm nice to stupid people. Really? Yeah, I have patience. I understand that something may have happened to them. Maybe. I'm still stuck in. Yeah, it's hard, I know. I don't wanna leave there. Yeah, I have patience. I understand that something may have happened to them, you know? Maybe. I'm still stuck in...

Yeah, it's hard. I know. I don't want to leave there. Yeah. Yeah. So, you know, ignorance and stupidity, two different things sometimes. Yeah, that's true. That's true.

But after the panic attack, you decided to spend more time alone. Yes. And you began rereading self-help books that you could find. And you write that most self-help books pretty much say the same things, but certain ideas resonate. What stuck with you? The idea of putting out positivity and energy like your energy field. I always thought that was kind of annoying to hear about.

And then you realize that it's scientific. Actually when you have positive thoughts, you're stronger, you're healthier, you're optimistic, you have a different look on your face, and you attract more positivity. And there's a magnetism there. And that is true and the scientific and your energy is not imagined, you know, it's not in my anyone's imagination. So learning about that in a scientific way was very helpful to me because it's the power of positive thinking.

It's the power of being optimistic in the dark and not going down a wormhole like, you know, the first Trump presidency, for instance, I let it take me down and I let it steal my joy. And I'm not going to do that again. You don't get my joy again. You know? So how do you prevent that? A lot of people, I get contacted by people all the time. I know. What am I going to do now? I know. I know you do. I was just sitting backstage asking you the same thing. What do we do now? But we'll figure out what we're going to do.

It's just one foot in front of the other. Everything is happening so fast. I don't doubt that we're going to get organized and figure out what the hell to do. I'm ready. Let's go. I mean, did anyone vote for Elon Musk to be the president? I mean, can't we come together, Republicans and Democrats,

and say we don't want that? Can't we agree on that at least? We can. we can absolutely. Do you feel political right now? Do you feel like you're in a, because a lot of people want to just check out. Yeah, I relate to that a lot. I feel a little disassociated right now.

I mean, it's hard, you know, you're promoting something and everything is happening in the background. It's like two different elements of my life. Like I want something, you're promoting something and everything is happening in the background. It's like two different elements of my life. Like I want something, I'm promoting something that's very joyful and happy. I have my stand-up special coming out, another joyful, happy thing. And with this as the backdrop, and it makes me realize like, you know, what my purpose is here is to bring a little bit light and levity and remind people to double down on your love to others and kindness and compassion to all

of the groups that are being targeted because people are really scared. And I hate that. I don't want people to feel that way. So what I can do in this moment is to be strong and be a beacon of light to people that feel hopeless and let them know they're not alone and that we're together, we're going to be together. And we have more people than they do. I know that. I know more people are good than they are, you know, terrible. I believe that. And I don't believe all Republicans are terrible. I just think, you know, I do think Trump is terrible. So let's get back to the parenting advice, which runs throughout the book, actually. You pay for your extended family's vacations. It sounds like a lot of fun.

You notice the kids were being entitled and so you wrote a letter where you reminded them some basic etiquette, which I'm gonna have you raise my kids. You wrote, do not consume copious amounts of alcohol that you did not pay for leaving the adults with no alcohol on multiple occasions. This is not a way to get invited back. This is solid advice, I have to say. How did your siblings react to you? It's their fault.

Any child's behavior is their parents' fault. So that letter was to my siblings as well. It was a letter after a vacation where the kids just treated this house that I rented on Martha's Vineyard that was so beautiful and so well-appointed. And these people did not want to rent their home. And my nieces and nephews were just so spoiled and entitled. And then I realized I was part of the problem for providing them with these vacations every year. Just wanting to spoil them, wanting to like, you know, show them how special life can be and how, you know, great it is to be

successful. And then I realized, oh, I'm part of the problem. So then I started taking the kids away without their parents. And so I can tell them how it is. And that's been going well too. I mean, my siblings don't like it because they're not going on the trips anymore, but I blame it on their bad parenting. Right. Okay, so they did. I'm going to write a book called Hot Parenting Tips.

Well, let me have some that you know how to talk to kids maybe because you've actually taken parenting classes. I took parenting classes. I never have taken a parenting class. I took online parenting classes for my ex-boyfriend's daughters. Okay. So I wanted to be, I wanted to understand children better and, and you know, I thought you could, you know, threaten them and that would, or you could bribe them.

I'd be like, if you do this, I'll give you this. And it's not about that at all. It's about being consistent and it's about meeting their moments. And when they're angry and they're mad, you never match their anger and their madness. You just show up with love. Like, oh, you're in a terrible mood. I still love you. I'm still sitting right here.

I'm not going anywhere. So you can be as mad as you want, but I love you. So what are the top three mistakes you see parents make? Well, first of all, people don't see their own children clearly. They are so biased. So you can't parent when it's your own child because you can't see how damaging it is. So good luck, I guess.

No, but just treating children like human beings instead of like children or adults, like really meeting them where they are, being on their level. If they're on the ground, get on the ground, you know, and sit with them and be interested in what they're talking about. Everyone just wants to be seen. Every person wants to be seen.

That's really the truth of the matter. And when you feel seen, then you feel like yourself and you don't feel judged and you can express yourself. And that's what we want. We want everyone to be... I want everyone to have like an injection of confidence and feeling seen. Like that really makes a difference in a kid's life. It does, absolutely. I had one teacher who just told me that I was gonna be the shit.

Her name was Mrs. Sheckman, she died last year in Florida, and she made me believe in myself. And I was the youngest of six kids, so there was a lot of neglect and there was, I mean, it wasn't a terrible childhood by any means, but there was a lot of neglect. They didn't pick me up from school. They'd forget about me all the time.

Well, you were number six. I was number six, yeah. And so I don't know why my mom didn't know about birth control, but she did it. And my teacher really instilled in me like what I was gonna amount to and that I was going to be something. And I will never forget those words of encouragement.

So when I look at any young child who's been neglected, I wanna be that person for them. You should write a parenting book. I know. I just said that, Kara. I know, yeah. Pay attention. I know, but really you should. I'm sitting right across from you with a microphone and you're not even listening to me.

I understand, but you're not actually doing it right now. No, I'm not writing a book right now. I'm promoting this book. Give me a minute. All right. Jesus. My God. How much can I do? What do you think I am, you? That's true. You also write openly about your love life and you talk in the book how your relationship with comedian Joe Coy changed the way you look at love, even though it didn't work out. And although you want to find romantic love, you thought to yourself, men are becoming unfuckable. Talk about that.

I'm still having lots of sex with men, so they're not completely unfuckable. I read about that. I'm still having lots of sex with men, so they're not completely unfuckable. I read about that. And no, it's not all men. I don't want to be, I'm not a man hater. I just, we understand what's happening in this world and it's pretty obvious. And I'm, yes, I like a variety of men. I like men in my life.

I'm not a settled down kind of girl. I don't see that happening for myself. Never? I mean, I'll never say never. You talked a little bit about. I mean, whenever I'm in a. Never? I mean, I'll never say never. You talked a little bit about. I mean, whenever I'm in a relationship, I think, oh, this would be nice. And then eventually I'm done with that relationship. So I'm just not that type of person. I'm not going to

get married, spend my life with someone person. I like a lot of alone time. And then I like to come together and I just have different desires. I used to think that something was wrong with me and now I realize I'm totally normal, that a lot of people feel that way. And so I'm saying it because I want people to know you're not alone if you feel that way. You don't have to find a soulmate.

It's okay. But in a lot of ways you're still the same person. Tell the Woody Allen story from this book. It's one of the best stories. Woody Allen, I went to a dinner, I was with Katie Couric. Katie tells the story. She told the story differently and I'll tell you how she tells it. But Katie and I went to this dinner and there was all these random people in New York City and I'm sitting at a cross and there's two empty seats across from me and I'm up against this wall in this restaurant and in comes Sunni Previn and Woody Allen and I'm like, oh no.

Like I can't do this. There's no way that I will get through this dinner. Were you aware of this? No, I didn't know they were coming. I saw them walking in the restaurant and then they're walking toward the table and I'm like, no, no, no. And I'm kicking Katie under the table. I'm like, oh no, I'm going to have an outburst.

Like I'm going to. There's no way you can seat me across from Woody Allen. And she's like, can you wait? And I'm like across from Woody Allen, and she's like, can you wait? And I'm like, wait for what? And she's like, can you at least just wait to the end of the dinner? And I was like, I could try. And I mean, I did.

I was like, that's a fun experiment to like hold myself, you know? To exercise some sort of patience. And so I did. I waited and I waited and I waited. And I was asking him, like, I'm not fake at all. And I was being so fraudulent. I was asking him like I'm not fake at all and I was being so fraudulent I was asking him questions about all the movies he directed and then I mistakenly

thought he directed Annie and I was asking him about that and he was answering the questions which doesn't make any sense it was Annie Hall not Annie yeah I didn't say Annie Hall I was asking about Annie and he was talking about Annie but of mean, you know, of course he was because that's another little girl. Anyway, he at the end of the dinner, the place passed around Blackberry Cobbler, the server came in and plated everyone's Blackberry Cobbler. And I went and then I was like, you're going to get it now. And then Woody Allen took a bite of his Blackberry Cobbler and I leaned in and said to him and Sunni, so how did you two meet? That's great. I slept like a baby that night. I really did.

I was like, and then Katie was retelling the story, Katie Couric, and she was saying, she's like, I guess Chelsea forgot how they met because she asked them how did they meet? I'm like, no, Katie, I didn't forget how they met. That was very pointed. Oh, Katie. Yeah, I know. Katie and I go back and forth on this all the time. I just forgot how they met.

And the reaction? He spit Blackberry Cobbler out of his mouth. He was laughing. And then I got up and then she's kind of out of it, Sunni. I don't know what her story is, but she wasn't very present. She was just kind of all over the place. So I don't know if she heard me or not, but I was leaving anyway at that point. I just had to say that before I did leave.

And then Katie was like, time to go. So he laughed at your joke. Yeah, he did laugh. He did laugh. But you know, I wasn't laughing with him. I was laughing at him. Okay. Yeah.

I love that story. Oh, I wish I could do that. I'm gonna do that. Now you've taken- You do that to people all the time. All the time. I do, I do. But I'm going to do that. Now you've taken the- You do that to people all the time. All the time. All the time. I do.

I do. But that one is- Yeah. Thank you. I was proud of that moment. I wish I had had- Well, I've never had to do that. I had a moment like that with Piers Morgan once.

I was proud of that too. What did you do to him? He was interviewing me and I just said, you're such an asshole. He's reading his phone. This has been around the internet, so I'm sure some of you have seen this. And he's reading his phone while he's talking to me. And I'm like, you're a terrible interviewer. What are you inviting me on your show so you can read your phone?

He's like, what, what, what? And he's like, well, maybe you're not interesting enough. I'm like, that's a you problem. You invited me here. You have to ask me questions so that I can answer them instead of reading the fucking internet, you loser. So that was good. That went viral.

I liked that moment as well. He deserves that because he really is an asshole. Yeah, I would agree with you on that one. Support for this show comes from Smartsheet. You know that feeling when you get when you're so into a task that the world around you goes quiet? Maybe you're out for a run and start to feel like you're flying. Or maybe you're playing guitar and an hour's divide. Or maybe you're so focused on a work task that you actually forget it's work.

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no matter the scale or complexity of their work. Let time stop, let the world fall away. Smartsheet can handle the rest. Smartsheet, where work flows. Visit Smartsheet.com slash Vox today to learn more. So let's talk about the business of being Chelsea. And a few things. This is a seventh consecutive New York Times bestselling book, your publishing phenomenon.

You grew up reading Moby Dick and a bunch of other books as a child. My father forced me to read these big books when I was like eight and seven years old. They were so inappropriate. Anna Karenina. I read Anna Karenina by Tolstoy when I was eight. I had to give a book report in our kitchen. And then I had to read Moby Dick and then he made me read East of Eden by John Steinbeck when I was eight. I wanted to kill my father. I had nothing in common with any of my colleagues at school. I would go, they would be like Humpty Dumpty sat on a wall. I'm like which one China or Berlin? I was had nothing, no relatability to like six year olds.

So. What do you, how do you think when you write, you know, sort of about art versus commerce when you're writing? I don't, I don't think of, I don't think that if you're not being authentically who you are, if you're me and you make a living at being yourself, you have to be very honest and very, I have to show all the good, the bad, the ugly. That's what the people that respect me and are looking to consume my stuff

are looking for is honesty. And that is what I base everything off of. I'm gonna give you the honest truth of what's happening in my life right now. I'm gonna make you laugh. I'm gonna hopefully inspire you. And I'm probably gonna make you cry too. And I'm gonna do all of those things and I'm gonna be very

Intentional about it. It's not yes. I'm making a living but I'm not I'm not for sale Is there anything you don't share? I? Mean certain people want to be private so, you know some people I don't tell their secrets You know I had it took me a long time to understand that my stories are not always just my stories. They're other people's stories, private people, and not everybody wants their story over the loudspeaker. So I've learned to shroud people's identities and to be respectful of people who don't want

to be in the public eye. So my relationships with men, for instance, I don't want anyone to even have to deal with what I deal with. People can't deal with that. They wouldn't last two days, you know? So I like to keep, like, my romantic interests, like, now. I've had a public relationship. Like, I hope I don't do that again. Right. Have another one.

Yeah, I hope I don't date another public person. Okay. All right. Besides the book, as you said, you have a line of vodka lemonade. You got a stand-up special. Netflix. My new stand-up special. Netflix, my new stand-up special comes out March 25th. It's called The Feeling. It's called The Feeling.

Yeah, The Feeling. You've got a podcast, Dear Chelsea, this European tour. What are the real money makers here? Stack rank them and give me a sense of how each fits into your overall business strategy. No, Kara. Why not? Because I don't know, honestly. I don't know. You don don't know you don't actually know

I mean I don't have to really think about how much money I make off of I make a good living right I get that But what do you what does best for you from that surprised touring probably stand up? Yeah, you make the most that you make cash and you go around, you know I mean not European tour right that's kind of just you know, but in America, you know, you do a hundred shows You make a lot of money. And that's your best, still remains. Is it changed over time? Is podcasting or anything? Podcasting, I make a lot of money doing that too. I mean, I've been doing my podcast for a long time, but touring is where the, you know, you make the most money. Are you surprised by how well comics are doing online?

Yeah, I love it. I mean, look at how many female comics are coming up. I mean, I have so many amazing, fierce female comics. They're all here at the festival too, that are coming up, that open for me, that I see, that I have specials out. Like, it is a turning into a very level playing field. We are not there yet, but it is turning into a level playing field, a more level. Do you lean into online more, like YouTube specials, things like that? You obviously this is on Netflix, which is a streamer. But how do you think about that?

For me personally, I just, you know, that's Netflix is the place to be right now for a stand up specials. It used to be HBO. It used to be HBO, yeah, then it was Netflix, and now all these other people are trying to, but it's still Netflix. That's where people go to watch specials,

and it's in the most households. So if you want an international business, you want to be on a platform that has the most, you know, households, obviously. And I have a long relationship with Netflix. I've been working for them since they started. I did their first talk show, I did a bunch of documentaries for Netflix,

I did Ayahuasca on Netflix. Yeah, I did one about, you know, white privilege. I've done a lot of really interesting things at Netflix. And so we have a great working relationship. And I'm happy to do my stand-up specials there. And any other business I do, any other TV stuff I might have coming down the road, that's not, you know, I'm not exclusive to Netflix.

Then I would go pitch it to other outlets and you find the best partner. The stand-up special, you get in some topics covering the book, but it's tonally, it's edgier. How do you, do you think the audience that reads your books versus the one that watches you in standup, do you think you have an overlap there with the audiences? I'm sure there's an overlap.

I mean, you know, some of this, there's overlap in some of the material because when you're writing a book, you can really set the scene, you can set the characters, you can set the dialogue, you can get into the real details about certain situations and standup, your driving force is the punchline and the joke of the story and the dialogue, you can get into the real details about certain situations. And stand up, your driving force is the punchline and the joke of the story and the funny. But they're both, you know, I'm a storyteller, I'm telling my personal story.

So there's definitely, you know, the Cuomo, my almost penetration with Governor Cuomo is in the stand up and in the book. Are you going to go back to that now that he's running for mayor? Now that he's the mayor? Now that he's running for mayor? No, no, I'm not interested in Andrew Cuomo anymore. Okay. But I was for a hot minute when everyone else was during COVID. I like that you kept texting him even though there was no response. Yeah, I did too. I liked that I was doing that too. It was funny. My family's like, you have no shame. I'm like, who gives a shit?

You know what I mean? This is going to be a really funny story. The one with President. I guess what it is. You did one with President Bush saying I'm good enough for a president, but not a governor. Once I was at President Bush's house I'm good enough for a president, but not a governor. Once I was at President Bush's house at Kenny Bunkport, I took a selfie with him and sent it to Andrew Cuomo. And I said, good enough for a president, but not good enough for a governor. Yeah.

What if he texted you right now? Andrew Cuomo? Oh, I don't give a shit about Andrew Cuomo anymore. I mean, that's the thing about heartbreak. You forget about him. I mean, out with the thing about heartbreak, you forget about him. I mean, out with the old, in with the new. I've had my heart broken many times since then. Well, you missed that bullet.

Yeah, I did. I dodged that bullet. As my sister says, our mom, our dead mother, is upstairs in heaven making sure I don't get canceled. I'm like, really? By cock blocking me on the ground? Right, that's true. That was a good one, though.

Yeah. She's not wrong. My mom is protecting me. Yeah, that's true. I mean, if I had been with him, I might have a good one though. Yeah, she's not wrong. My mom is protecting me. Yeah, that's true. I mean, if I had been with him, I might have gotten canceled too. Yeah, yeah. But now he's back. So yeah, there you have it. There you go. No one gets canceled really. So streamers are famously guarded with their data, which gives a lot of leverage. I recently interviewed Ben Stiller about severance, and he talked about how strange it was to essentially fly blind when you're negotiating with streamers

who have no data on viewership. How do you think about it? Do you do that yourself, or do you let your agents? I get data on my viewership. Yeah, they give it to you. I mean, I think they play games when you're negotiating to not give it to you. Or they underplay it, maybe.

But I don't know. It's kind of information that's accessible at this point. There's nothing secret anymore. Let's end up talking about politics again last time. How do you tackle him, comedians tackle him now? Trump? Yeah. I mean, Trump is just the same as he's always been.

He's a buffoon, he's an orange orangutan. I mean, what, he's, what is there more, there's nothing, there's no new information. It's the same old shit. You know, you have to tell him he's wonderful and great and then he's nice to you. And watching world leaders, like watching him threaten the world and make enemies out of our allies is horrifying.

That's not what we want. We're not, we don't want to be, we're not in bed with Russia. That's not what America stands for. America has want to be, we're not in bed with Russia. That's not what America stands for. America has not accomplished what we were set out to do. This democracy and this dream of democracy, we still have not accomplished it. It's an idea of what could be. We've never been it.

It's the idea. So we are still going to go in that direction of that idea. You know, after these four years are over, I hope we're still in a position that we are still going after the ideal of Americanism and what that means, and that we find some common ground with Republicans because this doesn't work anymore. It's like, this fighting and this hatefulness is not getting us anywhere.

So we have to figure out what the next solution is or the next step for a solution is, and I don't have the answer to that. So when I last interviewed, you said we're having a social justice and racial justice movement. That's clearly over We seem to be in the middle of a different thing many comedians, especially white male comedians with podcasts are full-on Trump supporters Yeah, Trump adjacent talking Joe Rogan, Theo von Tim Dill and Andrew Schultz. I just did Theo von's podcast

And we did not discuss Donald Trump, right? Didn't come up once Wow interesting I was I was totally fine if it had come up, but he didn't bring it up because obviously, why would he? Do you think some are scared? You host the Critics' Choice Awards. You basically implied Melania Trump was a sex worker. I think that's the new word now. But Trump-

It's flight attendant. She's a flight attendant. But Trump was barely mentioned at the Oscars. Do you think Hollywood is going to meet the moment? Comics are going to meet the moment? Yeah, I think Hollywood's doing its own thing and moving forward in its own thing. Hollywood has a big impact on social justice, and it has a big impact on what we see and the stories that are being told,

and representing all of the people that are being targeted by this administration. So I think Hollywood is kind of a nice antidote to this administration in many ways. But do you see pulling back or are you scared in any way to do that? I mean, I'm sure I'm a target, but am I pulling back? No. Clearly not. No, I'm not going to pull back. I mean, I'd like to make sure when I'm making comments about these things that there's a point to it, not just sounding off and bitching and moaning, because that I realized during the last administration how futile that is, and you're wasting your words and your energy. So it's important to have a mission and understand when to speak up and what to say when you're wasting your words, you know, and your energy. So it's important to be like, it's important to have a mission

and understand when to speak up and what to say when you're speaking up and not to just be screaming the whole time. So last question, semi-clad skiing is your birthday tradition. Any working, now that you're 50, happy belated birthday. Thank you. Are you working on any new traditions?

New traditions? Yeah. No. You like skiing naked? I ski in bathing suits a lot. I'm not naked anymore. My nephews asked me to not do that again. And I said, it's very, I said that you guys should take it as a compliment that your friends are talking about my body in that way.

Like I'm very relevant to your teenage friends. And they're like, we don't want to hear them talking about your boobs. And I'm like, okay, this is exactly why I didn't have children so that nobody could tell me what to do. But now I have to. You know, they're my nephews. I don't want them to be embarrassed about me. So I put my top on.

I don't ski naked anymore. But I do ski in a bathing suit with a jointed Margarita every birthday. Yeah. And I think it's a great. You're going to continue it into your 60s. Singing the song of freedom for women, you know, everywhere. It's like, come on, I'll have what I'm having. What's the title of your book that you released on your 60th birthday?

The wheels are off, but the train is still going. I don't know. All right. On that note, Chelsea Handel. Thank you, guys. Thank you. That was fun, Kara. On with Kara Swisher is produced by Christian Castor-Russell, Kateri Yocum, Dave Shaw, Megan Burney, Megan Cunane, and Kaylin Lynch.

Nishat Kurwa is Vox Media's executive producer of audio. Special thanks to Kate Gallagher. Our engineers are Rick Kwan and Fernando Arruda and our theme music is by Trackademics. If you're already following the show, you get a skiing invite from Chelsea, LSD optional. If not, you're stuck on a lift with Piers Morgan. Go wherever you listen to podcasts, search for On with Kara Swisher and hit follow. Thanks for listening to On with Kara Swisher from New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Monday with more.

Media Podcast Network and us will be back on Monday with more. Thanks to Smartsheet for their support. Blockers, friction and distractions destroy human potential and yet the workplace is full of them. Smartsheet is designed to remove friction and allow work to flow. Its innovative platform is designed to align with diverse work styles rather than forcing teams to adapt to inflexible systems. Whether your team is managing projects or scaling operations, Smartsheet gives you the tools

to cut through the chaos and keep work flowing. With Smartsheet, the extraordinary is just another day at work. Smartsheet, where work flows. Visit smartsheet.com slash Fox today to learn more. Fox Creative. This is advertiser content brought to you by the all new Nissan Murano. Okay, that email is done.

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One, two, three, four. Exhale. One, two, three, four. Ooh, who knew a driver's seat could give such a good massage? Wow, this is so nice. Oops, that was my exit. Oh well that's fine I've got time. After the meeting I gotta remember to schedule flights for our girls trip but that's for later. Sun on my skin, wind in my hair, I feel good. Turn the music up.

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