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

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 platforms and icon status for a purpose.

MENTIONED IN THE EPISODE:

00:28 – Stuart Weitzman

14:19 – Cindy Crawford

31:46 – Jason Alexander

Watch Stuart Weitzman’s full episode: https://www.youtube.com/watch?v=K9L9ONP5zj4

Watch Cindy Crawford’s full episode: https://www.youtube.com/watch?v=1roVoyCurrY

Watch Jason Alexander’s full episode: https://www.youtube.com/watch?v=MOH30l2BcWM