Chelsea Handler on Men, Trump & Money (+ Excellent Parenting Advice)

It's on! comedian, and seven-time best-selling author, Chelsea Handler. She has a new Netflix special titled 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.
Thank you. teaching T-cells to attack cancer, and eliminating cybersecurity threats with AI.
As one of America's leading research universities, they are putting big ideas to work in new and novel ways. At UC San Diego, research moves the world forward.
Learn more at ucsd.edu slash research. Anna Kendrick and Blake Lively return in another simple favor, a sequel to Paul Feig's dark comedy thriller, A Simple Favor.
Frenemies Stephanie Smothers and Emily Nelson, played by Anna Kendrick and Blake Lively, reunite on the beautiful island of Capri for Emily's grandiose wedding, where revenge is a dish best served chilled with a twist. And with more twists than the winding roads of Capri, it will keep you on the edge of your seat from start to finish.
Another Simple Favor premieres May 1st only on Prime Video. It is on! Yay! Yay! we're here

finally

the only person

I really know

I had a great time

with Elizabeth Warren

yesterday

but I'm super excited

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

Thank you. 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. It debuted.
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.
And thank you so much. I'm very, 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. Yeah.
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 was 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 give it, you 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 to spread it.
Excellent. So you also dedicated the book to stewardesses AND I THINK THAT'S A GOOD

AND I THINK THAT'S A GOOD

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AND I THINK THAT'S A GOOD

AND I THINK THAT'S A GOOD

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AND I THINK THAT'S A GOOD

AND I THINK THAT'S A GOOD

AND I THINK THAT'S A GOOD

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AND I THINK THAT'S A GOOD

AND I THINK THAT'S A GOOD

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AND I THINK THAT'S A GOOD AND I THINK THAT'S A GOOD AND I THINK THAT'S A GOOD AND I THINK THAT'S A GOOD AND I THINK THAT'S A GOOD AND I THINK THAT'S A GOOD 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.
Okay. Please get with the program.
I know you're flying around privately, but try and remember us small people, please. Flight attendants.
Flight attendants. Mostly women, though.
You didn't say 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- And let me just say you wanted to from the early time.
You walked through first class and said, these are my people. 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. It's like 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 and act as a flight attendant, yes.
Yes, yeah. 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.
Yeah. 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 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. 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? Yeah, I know. So the kids were kind of left by the wayside.
And my ex-boyfriend and his relationship with his girls just hurt me. 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.
And he's very confused all the time. I was also very confused, but they are 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. Well, you do have comedy about hating children.
I mean, I want to 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 have. 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 life, 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, I'm so, you know, 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, you know, 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.
You know, 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. Some people aren't good at that.
So it's good to know. But you seem to be good.
I'm good at helping out. 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. You know, 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, you know, 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 year? 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. Bathing suits.

Yes.

Yes.

It was very joyful.

Was it?

Yeah, it sounds like it.

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 for me.

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 going to break the Guinness Book of World Records

in Palisades Tahoe Friday, March 14th.

Thank you. We're doing it for Gold Bond.
We're doing a ski event that was inspired by my birthday videos. We're going to break the Guinness Book of World Records in Palisades, Tahoe, 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, no.
So one of the things you said the book is about female sisterhood togetherness. Let's stick to 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 J.D. 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, you know, 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, you know, not having, like, that's just so antiquated and it's so slow and it's so boring. We're so bored.
You know, I think the political situation we're in is a direct reflection of the fact that men are so scared of women. Like, why are you acting like this if they're not? Why would you overturn Roe v.
Wade after the Me Too movement? You know, 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 going to 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 it would, the smell would bother any of us.
And I was like, I want to 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 friend's 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 and they, and so I'm very hopeful about our young people. I think there's 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 going to see, you know, this, 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. 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.
You know, Biden was working off of Trump's economy and Trump is working off of Biden's economy. But people are so fucking 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 about money because the tax cuts will help people like yourself, right? It'll help.
Yeah, I don't need the help. I'm happy to give my money to the people that need it.
But 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, coming, coming, some funds. I support a lot of people.
So I'm like, can I get another, 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.
He has some money. 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. Is that a chance? 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, Cara.
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. All right.
Wow. But you should try it.
You do it. Why don't you do it, Cara? Does anyone here want to do it? No! No.
Wow, that's amazing. No.
So one of the things, though, 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 and 59 cents. 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 Owl's 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.

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So where does that entrepreneurial drive come from? Because you I've been very entrepreneurial as a career compared to a lot of people. Yes, 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.
No, I'm aware. I'm the same way.
Oh, yeah. Okay, good.
I thought you were saying what 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 podcasts.
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. 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 want to 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.
So, but one of the things you talked about, 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 a 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, it's when you go to therapy, it's so ironic because to get, I want to therapy to get my head out of my ass. I was, 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 you, 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, it's dirty. You know, 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, you know, 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.
You know, like I want to be patient when somebody's stupid. I want to be nice to them.
I don't want to 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, you know? I'm still stuck. 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, you know, 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.
It's not in 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, how do you prevent that? A lot of people I get contacted with 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 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 agree. 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're promoting something and everything is happening in the background.
It's like two different elements of my life. 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 be 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 noticed the kids were being entitled. And so you wrote a letter where you reminded them some basic etiquette, which I'm going to 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? Well, 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, wanting to spoil them, wanting to show them how special life can be and how 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. I'm going to write a book called Hot Parenting Tips.
Well, let me have some. You know how to talk to kids, maybe because you've actually taken parenting classes.
I took parenting classes. I've never taken a parenting class.
I took online parenting classes for my ex-boyfriend's daughters. Okay.
Because I wanted to understand children better. And I thought you could threaten them 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, you know, 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 going to 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, I wasn't, 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, and my teacher really instilled in me like what I was going to 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 want to

be that person for them. You should write a parenting book.
I know. I just said that,

Kara. 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.
I mean,

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.
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. Ever? 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 a going to get married, spend my life with someone person. I like a little bit of, I like a lot of alone time.
And then I like to come together and, you know, 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 the best. It's one of the best.
Woody Allen. I went to a dinner.
I was with Katie Couric. Katie tells this 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 across, and there's two empty seats across from me, and I'm up against this wall in this restaurant.
And in comes Suni Previn and Woody Allen. And I'm like, oh no, 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 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, 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 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 course, I mean, you know,

of course he was

because that's another little girl.

Anyway, he...

At the end of the dinner,

they passed around Blackberry Cobbler.

The server came in

and plated everyone's Blackberry Cobbler.

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 Sun Yi, so how did you two meet? That's great. I slept like a baby that night.
I really did. 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. Like I just forgot how they met.
Yeah. 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, Suni.
I don't know what her story is, but she wasn't very present. Like, 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. I wish I could do that.
I'm going to do that. Now you've taken the good- You do that to people all the time.
All the time. I do.
I do. But that one is- Thank you.
I was proud of that moment. I wish I had- Well, I've never had to do it.
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. You know, he's reading his phone.
This has been around the internet. So I'm sure some of you have seen this.
Yeah. And he's like reading his phone while he's talking to me.
Yeah. 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 like that moment as well.

He deserves that because he really is an asshole.

Yeah, I would agree with you on that one. Are you still quoting 30-year-old movies? Have you said cool beans in the past 90 days? Do you think Discover isn't widely accepted? If this sounds like you, you're stuck in the past.
This is the 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.
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.
They would be like Humpty Dumpty sat on a wall. I'm like, which one, China or Berlin? I had nothing, no relatability to like six, six year olds.
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 going to give you the honest truth of what's happening in my life right now. I'm going to make you laugh.
I'm going to hopefully inspire you and I'm, and I'm probably going to make you cry too. And I'm going to do all of those things and I'm going to be very intentional about it.
It's not, yes, I'm making a living, but 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, lemonades. You've got a standup special.
Netflix. My new standup special comes out March 25th.
25th. It's called The Feeling.
It's called The Feeling. Yeah, The Feeling.
You've got a podcast here, Chelsea, this European tour. What are the real moneymakers here? Stack rank them and give me a sense of how each fits into your overall business strategy.
Oh, Kara. Why not? Because I don't know, honestly.
I don't know. You don't actually know? No.
I mean, I have to really think about how much money I make off of it. I make a good living.
Right. I get that.
But what does best for you that surprised you? Touring, probably stand-up. Yeah.
You make cash and you go around, you know. I mean, not European tour.
That's kind of just, you know. But in America, you know, you do 100 shows, you make a lot of money.
And that's your best still remains. Has 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 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. It is 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? Obviously, this is on Netflix, which is a streamer, but how do you think about that? For me, personally? Yeah.
I just, you know, Netflix is the place to be right now for 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 households, obviously. And I have a long relationship with Netflix.
I've been working for them since they started. Right.
I did their first talk show. I did a bunch of documentaries for Netflix.
I did ayahuasca on Netflix. Yeah, I did.
I did a 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'm happy to do my standup 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 standup 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 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 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.
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 at Kennebunkport, 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? Yeah.
Oh, I don't give a shit about Andrew Cuomo anymore. I mean, that's the thing about heartbreak.
You know, 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, mom is up, 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? 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 gotten canceled, too. Yeah.
Yeah. But now he's back.
Yeah. 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. You can't really, there's nothing secret anymore.
Let's end up talking about politics again last time. How do you tackle him? Communions tackle him now? Trump? Yeah.
I mean, Trump is just the same as he's always been. He's a buffoon.
You know, he's an orange orangutan. I mean, he's, what is there more? There's nothing, there's no new information.
Right. It's the same old shit.
You know, you have to tell him he's he's what is there more there's nothing there's no new information right it's the same old shit you know he 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 no we don't want to be we're not we're in bed with russia that's not what america stands for america 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 or Trump adjacent. I'm talking Joe Rogan, Theo Vaughn, Tim Dillon, Andrew Schultz.
I just did Theo Vaughn's podcast. And? We did not discuss Donald Trump.
Right. Didn't come up once.
Wow, interesting. 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.
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 don't think.
I think we're kind of, I think Hollywood's kind of doing its own thing and moving forward in its own thing. And 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, 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, 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 joint and a margarita every birthday.

Yeah.

And I think it's a great – you're going to continue it into your 60s.

There's a singing 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 Handler.
Thank you, guys. Thank you.
That was fun, Cara. On with Cara Swisher is produced by

Christian Castor-Russell, Gutteri Yoakum, Dave Shaw,

Megan Burney, Megan Cunane, and Kaylin Lynch.

Nishat Kerwa 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,

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