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On with Kara Swisher

Pretty Tough with Maria Sharapova: Chelsea Handler

5/25/202641 min

Happy Memorial Day from all of us at On with Kara Swisher! Today, we’re bringing you a special episode of "⁠Pretty Tough⁠," a new podcast from the Vox Media Podcast Network hosted by tennis star and entrepreneur Maria Sharapova. Each week, Maria sits down with high-achieving women across industries for candid, wide-ranging conversations about their pursuit of excellence without apology. In this episode, Maria speaks with comedian and best-selling author Chelsea Handler, who's built a career on saying exactly what she thinks, regardless of the consequences. Maria explores what drives Chelsea’s independence across every chapter of her life and how she continues to evolve through therapy, travel, and psychedelics. Pretty Tough is produced in partnership with VOX MEDIA. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Clips

LSD in Aspen
Marriage? No Thanks
New Hulu Show Reveal
Never Live With Men
Body Image Confession

Transcript preview

First 90 seconds

  1. Maria Sharapova· Host0:00

    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. Maria's interviews are as tough as her backhand, and you all know how fun Chelsea is to talk to, so stick around.

  2. Chelsea Handler· Guest0:39

    You are the only person on your team that knows me, so you should be able to handle the situation, Maria. [laughs] You have a podcast now, and you need to start acting like it.

  3. Maria Sharapova· Host0:46

    I need to be a professional.

  4. Chelsea Handler· Guest0:47

    Yeah.

  5. Maria Sharapova· Host0:48

    Teach me.

  6. Chelsea Handler· Guest0:48

    You're a podcast bruh now.

  7. Maria Sharapova· Host0:49

    Teach me.

  8. Chelsea Handler· Guest0:50

    You're a podcast bro.

  9. Maria Sharapova· Host0:50

    What's the first step as a podcaster?

  10. Chelsea Handler· Guest0:52

    Uh, well, you have to ask lots of questions, which is, like- Yeah ... annoying, I know, for you It's really annoying ... it's, but it's, 'cause it's a totally different skill set.

  11. Maria Sharapova· Host0:58

    Well, it's so annoying interviewing you 'cause you ultimately lead the conversation. So I, I just give- Well, but that's gonna be a gift for you because it's gonna be easy. Is it?

  12. Chelsea Handler· Guest1:05

    Because you're gonna be able to ask me a question, and then I'm gonna be able to expound on it for so long that you don't even have to ask that many questions.

  13. Maria Sharapova· Host1:11

    Should I just leave then?

  14. Chelsea Handler· Guest1:12

    [laughs] Maybe.

  15. Maria Sharapova· Host1:14

    Okay. This is over. [laughs] [gentle music] My next guest and I are polar opposites. Comedian Chelsea Handler has built a career on saying exactly what's on her mind,

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