Something incredible seems to happen in Chance the Rapper's life every day. The latest: he sat down for Yahoo anchor Katie Couric at legendary Chicago restaurant Harold's Chicken Shack for a 15-minute discussion about Chicago, his family ties to Barack Obama, being independent, and more. A significant portion of the conversation focused on his signature "3" hat, which he declined to remove.

"There's only brain underneath here," he explained. "I don't take this hat off at all, ever. I sleep in this hat. I take showers and baths in this hat."

Later, he told Couric about how he pitched the Chicago White Sox to be their official spokesperson. "I wore a Sox hat everywhere," he said. "When I was making my cover for Coloring Book, I had a Sox hat on. And I was like, 'man, these Sox dudes never finished that deal for me. Take off the Sox cap. Then I was like, oh, this is my third project." He went on to explain the significance of the number 3: his relationship with his daughter and her mother, the holy trinity, and eventually, his three Grammys.

Chance explained why he chose to stay in Chicago full time. "I feel a certain beauty to Chicago, to my family that lives here, to people I grew up with that live here, to people I don't know that live here," he said. "I'm a plant. If you uproot a plant and put that somewhere else, it's not going to grow the same. So, this is where I'm supposed to be and where I'm supposed to grow."

When asked about the violence plaguing the city, he said, “What’s happening is bogus. As individual acts, it’s, you know, it’s terrifying and also sad. The respect for life is little [to] none in the city because we don’t really feel like people care about us. There’s a lot of things that I wasn’t exposed to or didn’t understand or know about until I went downtown. It’s literally like a different city over there.”