I grew up in Roseland. South Side kids want you to be so grounded and so real that it kind of takes away from your imagination and your possibilities. You’re so caught up in, “I can’t sell out.” To this day, people will be like, “What up, Hollywood?” But who’s writing me a check for being so Chicago and abiding by your rules? That stayed in my mind, which allowed me to embrace being different.

I moved into this low-income building in Chicago because all my friends lived there or the next building over rent-free. I had no rent to pay, no utilities, so I would save my money from standup. And then I started selling these jerseys I got from a hookup in Korea. I would pay like $10 and sell them for $300. I had money on top of money. So my apartment was lavish. It was like Eddie Murphy’s in Coming to America, where he had a Jacuzzi and shit. I had fur coats, but I would turn them inside out so people in the building wouldn’t see me living so lavishly. When I would bring girls back after a show, we’d pull up and they’d be like, “You live in this building?” Then we’d get inside and they’d go, “Goddamn! Chandeliers and shit? What the fuck?”

When I performed on the South Side, I had to alter my jokes in order for them to work. When I went up north, I would do it the way I had thought of it, but I felt like I wasn’t doing it Black enough. The North Side stuff was more thought provoking. That’s the best way I can put it. But I went, I bet there’s some thought-provoking Black people on the South Side. Nobody was doing that kind of stuff there. Everybody was being relatable. Like, “Hey, anybody remember having a TV and the knob don’t work? But then you take some pliers and you put them on the TV and that’s how you turn the station? Y’all remember that?” And everybody would go, “Yeah, wasn’t that crazy?” Up north, they were like, “OK, you got the pliers on the TV. Now what? Why is it crazy?” So I started mixing up the worlds, doing thought-provoking shit on the South Side and relatable stuff on the North Side until I found this balance.

Bernie Mac was a god in Chicago. He went on Pervis Spann’s TV show and Pervis asked him about comedians who were coming up. Bernie named me and a couple others. And I remember him telling me, “If you can’t capitalize off me saying your name, you shouldn’t be in this.”

Common and I were backstage at the New Regal Theater before he was about to go on. He asked me, “Do you think I should do a song with R. Kelly?” R. Kelly had just gotten huge. I was like, “Hell, yeah. You’ll blow up.” And Common was like, “Yeah, that’s what I’m afraid of. Then you can’t outtop that song. Or I could keep doing what I’m doing and rock with my loyal fans. They’ll put me on to other people, and I’ll grow like that rather than going for quick fame.” And I said, “Man, that makes sense. I’m gonna do the same thing.” So we made a pact that night.

When I did The Tonight Show With Conan O’Brien, Conan came to my dressing room after and was like, “Man, that was great.” Then a week later my manager said he wanted to hire me to write for him. And I was like, “Eh, they want me to be at work at 7 in the morning? I go to bed at 7 in the morning. That’s not going to fit in my lifestyle.” I’m not looking at the magnitude of this job. My manager was just like, “No, you need to do this.” I wasn’t the kind of comic who fit in the white world, but Conan elevated who I already was. He saw the differences between us and went, “That’s the formula. You be who you are, I’ll be who I am. You don’t know what hummus is, I don’t know what the fuck collard greens are.” And it was magic.

The clocks in my house are set to Pacific time, but my watches are set to Chicago time. It just reminds me of home and keeps me in that mindset.