Before he was in Hamilton, Daveed Diggs was an aspiring actor, rapper and spoken word performer creating "a rap curriculum" for Bay Area schools. Marc talks with Daveed about how that was the perfect starting point for his eventual portrayal of Thomas Jefferson. They also talk about Oakland, Daveed's rap group Clipping, and his new movie Blindspotting, which he co-wrote as a kind of love letter to his always-changing hometown. Also, Marc gives Bob Newhart a call to talk about his new Audible series, Hi, Bob. This episode is sponsored by The Roast of Bruce Willis on Comedy Central, Squarespace, and Sennheiser.