Pretty Tough with Maria Sharapova

Chelsea Handler: Unfiltered, Independent, and Always Evolving

May 20, 2026·40 min
Episode Description from the Publisher

Comedian and best-selling author Chelsea Handler has built a career on saying exactly what she thinks, regardless of the consequences. From stand-up comedy and bestselling books to hit television shows, she’s never played by anyone else’s rules. Maria and Chelsea first connected at the 2012 Olympics and have been friends ever since.  Maria explores what drives Chelsea’s independence across every chapter of her life and how she continues to evolve through therapy, travel, and psychedelics. They discuss reinvention, freedom, and what it really means to live life on your own terms. Maria also asks the question she’s been curious about for years: after all the success, what keeps Chelsea pushing forward? The result is a conversation that is funny, honest, and unexpectedly thoughtful, everything you’d expect when Chelsea Handler is in the room. All that and more on this episode of Pretty Tough. Pretty Tough is produced in partnership with VOX MEDIA. Listen to every episode on your favorite podcast platform Follow Maria on Instagram  Follow Maria on X Follow Pretty Tough on Instagram Subscribe to Pretty Tough on Substack Learn more about your ad choices. Visit podcastchoices.com/adchoices

Podzilla Summary coming soon

Sign up to get notified when the full AI-powered summary is ready.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.

Listen to This Episode

Get summaries like this every morning.

Free AI-powered recaps of Pretty Tough with Maria Sharapova and your other favorite podcasts, delivered to your inbox.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.