Pretty Tough with Maria Sharapova: Chelsea Handler

On with Kara Swisher

New York Magazine

Society & Culture

4.2 • 3.2K Ratings

🗓️ 25 May 2026

⏱️ 44 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	Hi, everyone, from New York Magazine and the Vox Media Podcast Network. This is on with Kara Swisher,
0:04.9	and I'm Kara Swisher. Happy Memorial Day. We're off for the holiday, but we've still got something
0:09.9	special for you today. We're bringing you an episode of Tennis Star Maria Sharpova's new podcast,
0:15.1	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
0:22.6	favorite people, comedian Chelsea Handler. They talk about how Chelsea has managed to maintain her
0:27.8	independence over her decades-long career and what keeps her going now. Maria's interviews are as
0:33.2	tough as her backhand, and you all know how fun Chelsea is to talk to, so stick around.
0:39.5	You are the only person on your team that knows me, so you should be able to handle the
0:43.2	situation, Maria. You have a podcast now, and you need to start acting like it. I need to be a
0:47.0	professional. Yeah, you're a podcast, bruh, now. You're a podcast, bro. What's the first step as a
0:52.1	podcaster? Well, you have to ask lots of questions, which is like annoying, I know, for you.
0:56.6	It's really annoying.
0:57.4	Because it's a totally different skill set. Well, it's annoying interviewing you because you ultimately lead the conversation. Well, 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.
1:11.9	Should I just leave then?
1:13.4	Maybe. 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.
1:11.9	Should I just leave then?
1:13.3	Maybe.
1:15.0	Okay.
1:16.0	This is over.
1:21.4	My next guest and I are polar opposites.
1:25.2	Comedian Chelsea Handler has built a career on saying exactly what's on her mind,
1:29.8	whether it gets her in trouble or not. From stand-up to best-selling books and hit shows,
	...

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