Sherman “Dilla” Thomas has become the face of Chicago history on TikTok, TV and in tours. So Khalil and Ben go on a mission to find out how Dilla became the city’s number one booster. We hear how Thomas was influenced by the stories told by his father, a Chicago police officer, and the influence of hometown Black politicians who were making history right in front of him. But mainly, he says, he’s driven by curiosity about how the city became what it is, and he wanted to bond with his kids by becoming the coolest dad on TikTok.