BEST OF: The Icons, ft Cindy Crawford, Jason Alexander, and Stuart Weitzman

BEST OF: The Icons, ft Cindy Crawford, Jason Alexander, and Stuart Weitzman

August 25, 2026 · 35 min · Season 2

About this episode

Three icons discuss their journeys, Jewish identity, and the importance of using their platforms for a purpose.

What does it take to be a true icon?  Stuart Weitzman shares his journey from creating one sketch to building one of today’s most recognizable luxury shoe brands, how Aretha Franklin helped turn him into the “shoemaker to the stars,” and the Jewish values he carries into his philanthropy. He also reflects on what it means to have Jewish pride, and how we can pass it to the next generation. Cindy Crawford talks about authenticity being the key to true beauty, how she’s embraced raising her children in an interfaith household, why she loves celebrating the Jewish holidays, and her memories from her iconic photoshoot in Israel with IDF soldiers. She also explains why speaking out against antisemitism feels like basic humanity, and reflects on meeting Holocaust survivor Ella Mandel when she did the Borrowed Spotlight project. Jason Alexander explains how Jewish identity shapes his humor and values, how Seinfeld helped him realize that acting could be a form of service, and how his children discovered their own paths in Judaism. He also reflects on the moment he pushed back on Larry David over a portrayal he felt crossed the line. Three icons, one shared mission: to use their…

People in this episode

Host: Jonah Platt

Guests: Stuart Weitzman, Cindy Crawford, Jason Alexander

Topics covered

Keywords

Mentioned in this episode

Organizations: IDF

Books & works: Seinfeld

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