You often reference Chicago in your lyrics. How would you describe where you grew up?
I grew up on 87th and Stony Island, in the Chatham area, and it had a major influence on me. It had elements of street life but, at the same token, flashes of black prosperity. I had the world to look forward to.

You dropped out of college to put out your first album in 1992. How did your family react?
My mother was a teacher and became a principal, so she was definitely serious about education. She was like, “Are you crazy? You better stay in school. What is this rap stuff? We worked hard for you to go to school!” She was not too supportive, but then she did not know what the dream was.

You’ve collaborated with many people, from the Roots to Kanye West, but what never changes is your spontaneous style. I’ve heard you don’t write your words down.
That process started from being in Chicago and not having pen and paper. I’d be hanging out with friends, drinking beer, with nowhere to write songs down. I started remembering them in my head.

Over the years, your lyrics have covered abortion, politics, parenthood. Is the label “socially conscious artist” a misidentification or a point of pride?
When I think of a socially conscious artist, I think of Bob Marley, KRS-One, Stevie Wonder, Bono. For me to be a part of that, I embrace that.

You even recorded a song, “Changes,” with your daughter to support the Obama campaign.
I wanted that song to represent what I feel like Obama does: change, hope, aspiration. Especially, as men, we see images of a strong man who is charismatic, well spoken, multicultural, and sets the example. People ask me how I feel about his political activities, and I’m like, man, just by him being there, there’s a change.

You still make music—but now you’re starring in movies with Angelina Jolie.
I want to be Morgan Freeman’s age and doing films. Acting is now the primary thing.

And musically?
I’m working on a new album with two Chicago guys: No I.D. and Kanye West.

You’re in Chicago often. I hear you’re a Bulls fan.
I was a Bulls ball boy. I’m coming tomorrow for an event with Carlos Boozer. Oh, and I love Derrick Rose. I had a little frustration with them when I thought that Michael Jordan didn’t get done well.

How would you describe your Common Ground Foundation, which works with at-risk youth?
We have a place called the Lighthouse, in Englewood. We work with the same youth all through high school. We connected with [Chicago native] Dwyane Wade, and he contributed $100,000. It hurts when you think about what kids have to grow up in. Our responsibility is to provide a better place for them.