Pretty Tough with Maria Sharapova

Chelsea Handler: Unfiltered, Independent, and Always Evolving

May 20, 2026

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 psychedelic...

Willow Bay: Reimagining the Future of Women’s Sports

May 13, 2026

Willow Bay has spent her career telling powerful stories. Now, she’s helping reshape who gets to be at the center of them. As a longtime journalist and now the dean of USC Annenberg, Willow has worked across nearly every major television network, building a career at the intersection of media, leadership, and storytelling. Alongside her husband, Disney CEO Bob Iger, she’s also the co-owner of Angel City FC, one of the most valuable teams in women’s sports. Willow also shares her perspective...

Gabriela Hearst: Redefining Luxury Without the Hype

May 06, 2026

Gabriela Hearst is one of the most purpose-driven designers in fashion. She’s built her career slowly, intentionally, and entirely on her own terms. You may know her for dressing icons like Laura Dern, Jodie Foster, and Zoë Kravitz, or for redefining luxury through sustainability, from the first carbon-neutral runway show to creating a line made from 100% recycled cotton. But her story begins on a cattle ranch in Uruguay, where quality, durability, and respect for the land shaped everythin...