Broken Record with Rick Rubin, Malcolm Gladwell, Bruce Headlam and Justin Richmond Broken Record with Rick Rubin, Malcolm Gladwell, Bruce Headlam and Justin Richmond

Daveed Diggs on the Need for Artistic Expression | From Who's With Me? with W. Kamau Bell

Jul 21, 2026 · 1h 18m

Summary

W. Kamau Bell interviews Daveed Diggs about the importance of intentional work, family, and enduring male friendships, particularly his bond with Rafael Casal. They discuss Diggs' origins in Freestyle Love Supreme, the creation of Hamilton, and his ongoing commitment to Clipping. The conversation also touches on navigating the entertainment industry, from independent films to mainstream success, while reflecting on the value of artistic authenticity.

Topics discussed

Sponsorship and show introduction Host intro and guest preview Guest introduction: Daveed Diggs W. Kamau Bell's departure from UFC Josh Hokett incident and transphobia in sports Meeting Daveed Diggs and early career Identity as a rapper vs actor Independent filmmaking and creative process Hamilton's rise and cultural discourse Tony Awards moment and athletic background Friendship with Rafael and Blindspotting Navigating business and friendship dynamics Balancing fame, family, and travel Parenting and raising children Sponsorship break and return to conversation Life in Oakland and East Bay identity Community, activism, and local culture Personal mantras and expectations The Cool Hand Series and prison films Outro and sponsorships
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