Pretty Tough with Maria Sharapova: Chelsea Handler

What this episode covers

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

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Frequently Asked Questions

How long is this episode of On with Kara Swisher?

This episode is 41 minutes long.

When was this On with Kara Swisher episode published?

This episode was published on May 25, 2026.

What is this episode about?

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...

Can I download this On with Kara Swisher episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.