Oprah: When you were a boy, did you dream that the life you're living now was possible?
Sean: I always felt that I would be somebody, but it still surprises me. Like when I drive through Times Square and see my billboard. Or when I got a standing ovation on Broadway for my role in A Raisin in the Sun. Or when I finished the marathon. Or when I perform at Madison Square Garden. That's when I think, "I didn't know it would be like this."
Oprah: How does this reality—as we sit here in your East Hampton house—compare with your dream?
Sean: I can't say that I've fully achieved my dream yet. I'm just starting to evolve.
Oprah: What is your dream?
Sean: I want to have a cultural impact. I want to be an inspiration, to show people what can be done. I've always been a daydreamer. When the other kids were playing, I was listening to the roar at Yankee Stadium—I was always attracted to the roar of the crowd. I wanted to know: "What would make somebody roar like that?" I was always looking at the hustle and bustle of people working. I wanted to work.
Oprah: The first time a crowd roared for you, did you remember Yankee Stadium?
Sean: Yes. I once went to a Run-DMC concert at Madison Square Garden. Onstage, Run said, "This is my house, and I want everybody in my house to take off their Adidas and put 'em in the air!" Everybody did. That's how powerful hip-hop was [in the eighties]—it made everyone want to wear Adidas. I said to myself, "One day I'm going to be on that stage." The first night I played at the Garden, I could hear people chanting my name. As I looked out over the crowd, I was bugging out. It was incredible and definitely a blessing.
Oprah: Where does your strong work ethic come from?
Sean: My mother worked three jobs and my grandmother worked two. At an early age, I started my own paper route. Once I saw how you could service people and do a good job and get paid for it, I just wanted to be the best I could be in whatever I did.
Oprah: What is your favorite childhood memory?
Sean: Until I was 12, I lived in Harlem. Then we moved to Mount Vernon, New York. That was Mom's way of getting us out of the inner city after my father was killed [Melvin Combs was murdered when Sean was 2]. But my grandmother lived in Harlem, so I went back and forth. I remember the simple things about Mount Vernon: grass, trees, and being able to play baseball. In Harlem there was no Little League, no front yard with grass. But the neighborhood was multicultural, so that broadened my horizons.
Oprah: What did your mother tell you about your father?
Sean: She tried to protect me. My father was a hustler who sold drugs. During his time, that was the way out of Harlem—either that or playing basketball. My mother didn't want me to follow in his footsteps, so she was selective about which truths she told me: My father was in the army, and he owned a limousine service, and he died in a car accident. Actually, he was shot in a car. But even as a kid, I put two and two together. I noticed that guys from the streets in Harlem always seemed to know my family's last name. "I used to run with your father," they'd tell me. All my uncles were street hustlers as well.