Pretty Tough with Maria Sharapova: Chelsea Handler

0:00Kara Swisher:Hi, everyone from New York Magazine and the Vox Media Podcast Network. This is On with Kara Swisher, and I'm Kara Swisher. Happy Memorial Day. We're off for the holiday, but we've still got something special for you today. We're bringing you an episode of tennis star Maria Sharapova's new podcast, Pretty Tough. It's another great Vox Media podcast that you should be listening to. In this episode, Maria sits down with one of my favorite people, comedian Chelsea Handler. They talk about how Chelsea has managed to maintain her independence over her decades-long career and what keeps her going now.

0:31Kara Swisher:Maria's interviews are as tough as her backhand, and you all know how fun Chelsea is to talk to, so stick around. You are the only person on your team that knows me, so you should be able to handle the situation, Maria. You have a podcast now, and you need to start acting like it. I need to be a professional. Yeah, you're a podcast brah now. Teach me. You're a podcast bro. What's the first step as a podcaster? Well, you have to ask lots of questions, which is like annoying, I know, for you. It's really annoying. Because it's a totally different skill set. Well, it's annoying interviewing you because you ultimately lead the conversation.

1:02Well, but that's going to be a gift for you because it's going to be easier. Is it? Because you're going to be able to ask me a question and then I'm going to be able to expound on it for so long that you don't even have to ask that many questions. Should I just leave then? Maybe. Okay. This is over.

1:21My next guest and I are polar opposites. Comedian Chelsea Handler has built a career on saying exactly what's on her mind, whether it gets her in trouble or not. From stand-up to best-selling books and hit shows, she's never really followed anyone else's rules. She came to watch me play at the Olympics in 2012, and we've been friends ever since. What I've always found so impressive about Chelsea is her independence. She's created a life completely on her own terms. And she's constantly evolving, whether that's through therapy, travel, or yes, even psychedelics. So I had to ask her, after all the success, what keeps her pushing forward?

2:03And does she think I should try a little experimenting once in a while? As always, her answers surprised me. This was a fun one. because anytime Chelsea's around, I know I'm in for a funny, unfiltered, and incredibly thoughtful conversation. I'm Maria Sharapova, and this is Pretty Tough.

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4:37First of all, thank you for doing this. It means we like, this is like a testament to your loyalty, so I appreciate it. You're welcome. Yeah. I like to start these segments with a quote, and you've had a lot to say. So it was really challenging. Pulling a quote from you. But the one that I really favored was, I have to tell the truth because I'm incapable of anything else. Is that accurate? Is that a false? I can lie. You said it on Fallon. Yeah, well, I wouldn't qualify that as like a quote. You know what I mean? But you said it. Well, I, too, tell the truth most often. I don't lie a lot. I sometimes lie just to, you know, protect people's feelings.

5:16But as a general rule, especially as a woman, I believe it is very important to be truthful, A, with other women, and B, with everyone else. When was the last time the truth got you in trouble? Oh, all the time. The truth always gets me in trouble. Like today? I'm constantly running my mouth. I mean, I'm sure I'll say something in this interview that will get me into trouble. Or, I mean, at some point today, I have a lot of interviews today. So at some point, I will say something that will be like in the news, Chelsea Handler said this. Okay. And do you like that? No. No. I don't mean to do that.

5:49I just, it's my personality and I've learned to accept it. And the moment you feel it, like you're, the truth is gonna. Yes. Just be, I just like to be candid. Yeah, no. I don't like to be guarded. Do you know what I mean? Like you're more guarded because you've grown up like having to protect yourself in a way. I've kind of like made a living out of just showing like being myself rather, you know, like having my personality out there. So I forget sometimes that things are going to be taken out of context or sometimes they're not even taken out of context. I just shouldn't have said it. I shouldn't have been so forthcoming.

6:23I mean, most people struggle with being honest, but you don't because it's just you. That's you. Yeah. It's your personality? Yes, I think so. I think that's what I've learned in the 50 years that I've been with myself. I've learned that that is a big chunk of my personality is to just say what's on my mind. I mean, it's really admirable that you're 50 years old and you are growing and getting better and you're aware of it. Like, what are you still searching for? Well, I mean, you say 50 like it's over. And I would argue that 50, now that I am 50 and I understand life more than I did when I was 30 or 40, is that you get so much more wisdom and you get so much more experience that you actually feel like you're beginning again.

7:05Like when I turned 50, I was like, oh, this is a reset. Like I have my shit together now. I'm recalibrating. In a way that I didn't have my shit together in my 20s, 30s, or even my 40s. In my 40s, I went through like a real rough patch in my 40s. And I think it's probably called a midlife crisis because that's what happens when you turn that age. You start to really think about what's what are you contributing? Like, what's your purpose? Why are you here? Who are you here for? Are you making like people feel good? Are you making them feel bad? Like, what do you want to do with your life? So now that I'm 50 and I kind of went through all the ugly therapy part of really getting like into the stuff that you don't want to really talk about when you're younger, I feel like renewed and I feel very more I feel much more optimistic and happy in a way that I haven't felt in my life like I feel calm rather than crazy that worries me so I feel like you have a lot to look forward to and all women and men but I'm a woman so I'll speak to that have a lot more to look forward to like I always looked at 50 like oh I'll be dead by 50 it's like well No, no.

8:11Because of how much you drink? Well, partly, but also because of all the other shenanigans I get up to. Right. How often are you microdosing and psychedelicing? I had a microdose. I just came from Aspen. I was there for three days. I had a little LSD while I was there. That was the last time. And then I gave, I had about 10 little pieces of paper hits that I brought with me. And then I gave those to my friend when I left and said, would you like the rest of these? Because they lived in Aspen. And I felt like probably now is not a good time to travel with drugs. So I'm just leaving them all over the world.

8:42I never thought we'd get to a point where we'd be talking about traveling with drugs. Yes. But here we are. That's why you invited me on this podcast. I mean, knowing what you know about me, do you suggest I try psychedelics? I don't think that you are a drug person. I don't think that. What makes you think that? Well, you're Russian, so you like alcohol. That's just in your genes. That's in your DNA. I do. I like a drink. So that's enough for you. I don't think you're very like, I don't want to say controlling. No, controlling. Yeah, controlling. Yeah. No, I feel it when I'm not in control. You don't like it.

9:17No. Right. I don't mind being out of control because I'm always a little, even as high as you can get me, I still know what's happening. I mean, I have a question in my notes because I was listening to a few of your podcasts and I was like, God, she seems so in control. Is there anything that throws you off? Yes, but I think my experience, first of all, I have a very strong constitution. It takes me a lot of drinks to even like catch a buzz or to get drunk. Like I don't get drunk a lot. I mean, you've practiced. I've practiced since I was a little. Malcolm Gladwell is like really proud of you.

9:50If you put in 28 ,000 hours or whatever it is. I thought, yeah. 28 ,000 hours, 10 ,000 hours. I thought it was just 10 ,000 steps. Well, that's per day. You're getting those two things confused. I am. So 10 ,000 hours, 10 ,000 hours of something makes you an expert. I'm an expert in drinking and drug use.

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11:52I would argue that 50, now that I am 50 and I understand life more than I did when I was 30 or 40, is that you get so much more wisdom and you get so much more experience that you actually feel like you're beginning again. Check out Pretty Tough, new episodes on Wednesdays. You can watch it on YouTube or listen in your favorite podcast app.

12:15Kara Swisher:Hi, Kara here. On my podcast, I spend a lot of time talking to people at the top of their game, but there's a whole set of stories we don't hear nearly enough about. That's why I want to tell you about a new podcast at the Vox Media Podcast Network. It's called And Mom, and it's hosted by WNBA star Skylar Diggins and reporter Cassidy Hubbard. The show dives into what it actually looks like for women to perform at the highest levels of their careers while also navigating motherhood, something I know a thing or two about. Not polished, not sugar-coated, and on their own terms. It's the kind of honest, complicated conversation we need more of, especially in sports.

12:50Kara Swisher:The first episode of And Mom is out now with special guest Shawn Johnson. Check it out on YouTube or wherever you get your podcasts. You generally seem in control of everything, like the situation, a conversation, when you're on stage, when you're writing a book. Is there anything that throws you off balance? I guess when I'm when I feel uh maybe shunned or invisible that does throw me off balance I think if someone like knows me and doesn't isn't interested in talking to me that like if I'm at a party and I'm like oh hey and they're like not interested I'm like what oh you know like I get it so you care I yeah yeah yeah I care like that throws me off where I'm like oh But then I also don't harp on it.

13:39I'm like, oh, okay. But in the moment, you're sensitive to the fact that they've moved on before you want it to move on. Yeah, yeah. I can read the situation and go, oh, that person doesn't like me. In your last book, you dive into the value of spending a lot of time alone. Are you still spending time alone? Or now that you have like a hot new boyfriend, that's... Yeah, he's taking up a lot of my time. Okay. Is that good or bad? It's good. But he lives in Florida, which I know you love. You spent a lot of time in Florida. I did not anymore. Yeah, but you did. And I'll never forget that. Okay, that's passed.

14:12But now you're spending time in Florida? No, no, no, no, no. I'm a big in Florida. You refuse. I'm not big on Florida. No offense to Floridians. It's not them. It's the government situation. Yeah, yeah, okay. Political situation. But he's okay. He lives in Florida, and hopefully he will not be living there for that much longer. Because that's not a place that I'm interested in. Because he's going to move into. No, no, no. I will never live with a man. Not full time. Okay. No, I'm not interested in that. Even if you're deeply in love? Yeah, if we're deeply in love, you know, like I like long distance and I like space.

14:41So when I'm working, like I'm here in New York working for the next couple days, I want to be alone. I don't want somebody, you know, a plus one around. Yeah, I mean, you're very independent. Yeah. Yeah. So aside from making your own money, what are the ways that other women can be more independent? Maybe not to your extreme. No, no, right. I'm not a, yes, I understand that. But I think that, A, one way to, well, A, yeah, you should be trying to make your own money, definitely. But also, I think women's outlook towards men has shifted in, like, the last 10 years, at least from what I can tell, where there are many women that, like, are thinking about not being married.

15:21You're not married. No. And you have a baby. We have a baby. I feel like that's marriage plus. Yeah. Okay. Great. Exactly. So there's a lot of women that are thinking like what you're thinking. and also marriage seems a lot like a bit antiquated and I agree with that I feel like there's not really a reason to get married anymore really you know what I mean like it's just for a big fat party yeah and that's like I find I find the need or the I deal with this a lot on my podcast where people call in for advice right oh no I listened to I was like she's like she's a sex therapist a relationship she's just she's become a therapist yeah basically yeah yeah Yeah, I took all the things that I learned and gleaned from therapy and then just wanted to spit them right back out.

16:04It's really entertaining. I know. Thank you. I like it. It seems like you're enjoying. It gets deep. It gets quite serious. Yeah. Sometimes. I didn't intend for that to happen. So I'm like, you know, if somebody really needs help, I want to help them. But I think my advice to women would be like to not be so desperate to find your quote unquote one or the one. I think that's a load of garbage that we've all been fed. And this is coming from someone who's very interested in the relationship that I'm in right now, although I don't look at it attached to the outcome of the relationship. Like, he's here today.

16:38He could be gone next week. Does he have kids? No. And I won't be having kids with anyone. Right. So if he does want kids, he's going to have to do that with his next girlfriend. I mean, you've made that very clear for a long time. Yeah. I mean, if he's any questions about that, he can just refer to my Instagram. Yeah. Or one of your books. But. Does he have a name? Cowboy is his name. Okay. That's all you're going to give me? Yeah. Yeah, I mean, I'll tell you, but he doesn't need his name out there. I'd like to maintain some sort of privacy for him. Since when? Just since. Since I've been around the block a couple times and realized how I can just destroy people's lives, you know, by dating them, that all of a sudden they're out there.

17:11It's a fair point. In the public eye. It's not really fair. No. I just, that would be my big advice is to stop thinking about, like, that you're— The urgency. But I think the urgency of meeting a man comes from wanting to have children. Sometimes, but sometimes it's just about like finding the one and not necessarily even taking into account what comes after that. You know what I mean? It's like people want to be in love so badly. Right. And I think that that's... They want the idea of being in love. Yeah. And we've been sold this pile of goods that tells you like your value as a woman comes from being married, being a wife, being a mother, all of those things.

17:48So I would implore women to really just think about what it is you want individually and then go from there instead of thinking that that's what you're supposed to do because society tells you you're supposed to do it. you can have a full life. I mean, obviously my life is specific and unique, but you could have a very full life if you decide not to have a child without, you know, without all that stuff and being a single woman. No one shares those stories. Yes. Yeah. Right. I just, I want to take a second to acknowledge your posture. It's really good. Is it? Yeah. Wow. Thank you. So much better than mine.

18:21Really? Yeah. Well, you're so tall. You're probably always crouching over, right? Yeah. I don't want to see anyone. See, I have to because my boobies are so big that I have to make sure that I'm not... That they stick out. Yeah, that they stick out so people know that I'm coming. But now that you have a man, you don't need to do that anymore. Thank you. Or you need to do it more, I don't know. Yeah. Let's, can we talk about your career? Yeah. Do you still consider yourself a comedian, like, first and foremost? And I ask that as, like, from a point of view of, like, an identity. Because when I used to, like, being an athlete was a huge part of my identity, and it only had a certain limit.

18:54But the qualities, like the things that I learned in my experience through being an athlete is just continues to run through my life like even when I even when I fill out forms and they say what's your occupation even though I don't know what the hell my occupation is at the moment I still write athlete but now it's podcaster well whatever athlete slash podcaster what would you write that's a great I I think that every time I'm asked that and I just settle I've settled on comedian because it's like when am I going to write author you know like I I have thought about that but I don't identify yeah, I guess I strongly identify with the term comedian.

19:28And you're proud of it? Yeah. Yeah, I'm proud of it. I mean, I think of myself as more like I feel like a public figure. Do you know what I mean? But that's how I feel. Like I feel like it's not one thing or another. I just feel like I'm out there. What do you feel is your responsibility as a comedian? To bring joy and laughter and medicine because people need it. More so now than ever. Yeah. I want people to be happy and to remember, like, kindness, the kindness of strangers, to double down on, like, joyfulness and laughter. Like, laughter is really so important and healing. And being able to be, like, a perpetrator of that, to be able to get on stage and make people forget about how crazy the world is for an hour makes me feel very purposeful.

20:12Yeah, and I think maybe a few years back it was, like, purely entertainment. But now there's like a deeper. Yeah. When we get a chance to go and enjoy someone's performance and feel like it impacts our view or like if when I was competing and someone's had a really crab day and they watch me have a really crab day on the court, but I figure it out and I win. Yeah. Like to have that impact. Yeah. I feel like it's not just a moment. Like it's a feeling. It is. It's a feeling. And it's like you find it. I guess, you know, for me, I think and I think over the course of our lives, our purpose changes quite often.

20:46I mean, we're talking about it right now with you, right? Like your purpose changes. Like you're living, I think for our youth a lot, we're living for ourselves. Like what can I do? What do I want? What can I get? What am I, you know? And then I think as you kind of get older, you're like, what am I giving out? What am I? It's not just take, take, take. It's like, okay, let me share. It's hard to acknowledge that in your 20s, 30s. I think that develops over time. Because you're trying to identify who you are. So then you find your identity and then you like burrow into that. Right. And you want to feed it.

21:24And you want to be as successful as possible. Right. And then something happens. And then you get successful and you're like, well, what is it? Yeah. What is this? And then you're like, is this enough? Is this good enough? Is this enough of a contribution? And then you kind of recognize the selfishness in which you've led your life or for me anyway. That's how I felt like, oh, I'm pretty selfish. you know like what I just need another big house or like what do I need more money like what you know and so that then you start to kind of self-examine what's your relationship to money like how do you I like it yeah I mean you've always liked it from a young age like you flew first class since you were yeah I mean you earned it yeah I earned my own money and I like to spend my own money and I like to share money you do I'm very generous and I'm a generous tipper thank you always you've always you're also very generous emotionally like I remember yeah no I at the time like when I was really struggling in my career and I had a tough moment and I had the suspension you called me every single day and you checked in on me and you were like this asshole wrote this bad piece about you but then there was like 10 others that were really positive so I think today we're doing okay to have someone check in so you're you give that's nice no it's true it's it's um when anyone speaks about you and because they always like people always see talent and you know famous figures and in a very in a light that they want to like they have an idea and that's what they associate with that idea and i'm sure when i say oh i'm interviewing chelsea handler, like something comes up, right?

23:02And whether it's positive or negative, like they already have an opinion, whether it's about me, whether it's about you. But the first thing I say is how generous you are. Oh, that's so nice. Thank you. No, it's true. You've come up in a very different media or very different to how it is now, like with social media. If you were building, if you were starting to build your career today, how would you do it differently? Oh my God, I wouldn't even know where the fuck to begin. I wouldn't know how to do any of this because Because I've lived through like, and I mean, you two, even though you're younger than me, like we've lived, I lived, I got my first phone.

23:36Like the internet came out when I was like 19 years old. So I have my original email address. Like I have an AOL account still. What was your password? 0253. Mine was love and peace. Well, mine still is 0253. So please don't get into my account. I've been hacked. I've lived through the technology age. Now we're dealing with AI. Yes. Like I don't even know. It's too much of a whirlwind. I guess I would just start recording videos of myself. You know, it's probably not dissimilar. In your underwear and bra. Yeah, and start telling jokes or telling funny stories in the way in which I am known for now.

24:07And I would just be outspoken and probably just do what everybody else was doing. I don't know that I would have some great grand idea. Or I might just be so overwhelmed by it that I wouldn't even try. I'd be too nervous. Do you feel like you constantly have to feed this algorithm? rhythm, like just constantly providing content? It's pretty natural for me to provide content. So I don't feel like desperate in a sense. I just feel like, oh, that's easy. Let me make it. I like these kinds of videos. These are the reasons, you know, like let's do. Are you strategic about it? I mean, I have a social media team and I like kind of let them handle things.

24:45I need a little bit of that. Yeah, probably. It's I mean, because I don't want to be. So what you have an actual calendar of like when you're going to post something? They do. I mean, I don't have a calendar. But I mean, but like, you know, I'll be like, oh, I do this thing. Kids are not that great on my social media. So I'll film like five of those and then they'll put them out, you know, over the course of six months. What do you mean kids are not that great on your social? Like you don't have a lot of kids. I do like a video, like a PSA. Like, hey, you could be like, you could have a life like me too.