"If you could invite any person—dead or alive—to a dinner party, who would it be?" I ask.
He leans forward in his rocking chair before venturing an answer. "Billie Holiday, Coretta Scott King," he finally says. "Malcolm X. I would ask him what he experienced at Mecca that so completely changed his life."
A moment later, the catchy refrain of Yung Joc's "I Know You See It" is piped in, and we're both snapping our fingers. For the next hour, the man who's gone by Puffy, Puff Daddy, P. Diddy—and now Diddy—is simply Sean with me.
Start reading Oprah's interview with Sean Combs
This interview appeared in the November 2006 issue of O, The Oprah Magazine.
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.
Oprah: Did you grow up longing for your father?
Sean: No. My mother played the role of a father, and my grandmother played the role of my mother. One day when I was about 9, I went to the store for my grandmother, and someone stole my money. I came home crying. My mother wouldn't let me in the house. She said, "Go back out there and get that money—and if anyone ever puts their hands on you, make sure they never do it again." She knew the reality—if people smell weakness, they take advantage of you. You have to defend yourself. On the other hand, my grandmother was like, "Come here, baby. I'll walk with you to the store." I'm not saying that my mom would never have let me in the house that day, but she was trying to teach me a lesson.
Oprah: You met Andre Harrell, who hired you at Uptown Records, when you were 19. Did that feel like a life-defining moment?
Sean: Yes. As I walked through the record company, I knew that it was exactly where I wanted to be. It felt like home.
Oprah: You shot up through the ranks, yet Andre eventually fired you. Did that lead to a kind of freedom?
Sean: I was like a wonder kid at Uptown. The first record I produced sold two million copies—and I'd only produced it because the producer didn't show up. My talent is definitely a gift. I don't understand where it comes from. I don't play an instrument, and I never went to school for music production, but I know exactly how a song should sound and how to give an artist direction.
Anyway, at Uptown, I sold a huge number of records. I was very passionate, and I didn't understand protocol or workplace politics. So I got fired because there can't be two kings in one castle. I wasn't trying to be disrespectful to Andre, but I was fighting so hard. He wanted to be more diplomatic and to make sure everybody felt involved. Getting fired was one of the best things that could have happened to me.
Oprah: What did it teach you?
Sean: It taught me that putting out a record is a team effort. It taught me how to motivate people. It taught me not to get caught up in my own hype. I'm glad I learned that at a young age. But still, I didn't want to go out like that. I didn't want to disappoint the person who put me in the game. Later I made it up to Andre by changing. Then he came and worked for me, so our roles were reversed.
Oprah: How did you get the name Puff Daddy?
Sean: It's a nickname somebody gave me.
Oprah: What does it mean?
Sean: I've never told anyone that. I know you get people to tell you everything, Oprah. But I can't look you in the eye and explain that one.
Oprah: So look away! Did they call you Puff because you were puffed up?
Sean: No, no, no. It's just a silly name.
Oprah: I can see that you're not going to tell me.
Sean: I'll answer every other question.
Oprah: Okay. Why do you keep changing your name? I read that you said you're going by just Diddy now because the P was getting between you and your fans.
Sean: The name change thing isn't serious. But during the Puff Daddy era, I got into a lot of trouble. [In 1999 he was charged with weapons possession and bribery after a shooting at a New York City nightclub and faced up to 15 years in prison. He was tried and acquitted in 2001.] After the trial, I just said, "I'm changing my name."
Oprah: Were you scared during that trial?
Sean: I was scared to death. I didn't commit the crime. There are so many things I want to do, and sitting in jail isn't one of them. But I knew the reality of how many people of color are convicted of crimes they didn't commit. I knew my chances of getting convicted were very high.
Oprah: A lot of people still think you committed the crime.
Sean: I can't get caught up in what people think. I can understand why they think that, but I know the truth.
Oprah: How did the trial change you?
Sean: It made me appreciate life more. As a young African-American male, you have to have your war face on at all times. But the trial humbled me.
Oprah: I was once on trial for six weeks for a show I did on mad cow disease. During that time, I was thinking, "My God, if I have to go to jail, I'll be terrified."
Sean: Fifteen years is a long time. They wanted to make an example of me. There are so many stereotypes about the rap world. So I thank God for Johnnie Cochran and others who defended me. I also thank God for the truth.
Oprah: Exactly. On another subject, do you like to give people a show? I'm thinking of your assistant Farnsworth Bentley holding your umbrella for you.
Sean: That was Bentley's idea, but I definitely love to entertain people. I'm from the school of P.T. Barnum.
Oprah: Do you remember your first kiss?
Sean: Yes. It was the greatest, though I had some pretty good kisses after that. I was 11, and the girl's name was Cindy. Her breath was like a baby's breath—so clean and good. I love to kiss.
Oprah: So that must make you a pretty good kisser.
Sean: I take my time!
Oprah: You're known for your legendary parties. What's the most fun you've had hosting?
Sean: I'd probably have to say the first White [clothing] Party. I wanted to strip away everyone's image and put us all in the same color, and on the same level. I had the craziest mix: some of my boys from Harlem; Leonardo DiCaprio, after he'd just finished Titanic. I had socialites there and relatives from down south. There were 200 people sitting out here, just having a down-home cookout. It lasted until the next morning.
Oprah: What makes a party great?
Sean: The energy of people. The details. The tone I set as the host. I want everyone eating, and I want to keep their glasses filled. I like bringing together people who wouldn't normally meet.
Oprah: When you're listening to an artist, how do you know when the person has what it takes—the voice, the charisma?
Sean: I look for the uncontrived. I like it when things are rough and raw, not by the book—when someone doesn't really know how to make a hit record, and they're just singing from inside themselves. There's a vulnerability. They know how to give of themselves.
Oprah: What did you feel the first time you heard Mary J. Blige?
Sean: Goose bumps. Her voice was so raw. It was a little uncomfortable.
Oprah: When it comes to lyrics, do you think your sense of responsibility has increased over the years?
Sean: People judge the lyrics without understanding the intention or background of rap. It started as a statement about young black life in the inner city. Rap was a way for artists to tell the world about how much danger we're really in—physically and emotionally. It was a way for us to speak out. But if someone hears the lyrics without understanding the impulse behind the music, they might see it solely as a glorification of violence. Tupac spoke the truth. He felt like millions of young men and women. And rap has evolved: From Biggie [Notorious B.I.G.] and Lauryn Hill to Wyclef Jean and Mos Def, rap is about what's really going on. But some people like to run away from the uncut truth.
Oprah: You know, I'm open to understanding where rap comes from. But my question to you is the same one I asked Jay-Z a month ago: Is it possible to have rap music without lyrics that demean women? Can we rap without calling women bitches or using the N word?
Sean: Yes, it is possible. Like every art form, hip-hop has to grow up, and in some ways, it is changing. The women in the hip-hop community have made sure we've noticed how disrespectful the lyrics are. And yet there are certain things that are happening in life: People are calling people bitches and hos. But hip-hop isn't just that.
Oprah: I understand that it's more. I'm asking about the parts that still demean women.
Sean: Demeaning women is not right. Violence is not right. Evil is not right. I'm not saying that hip-hop has been totally cleaned up, but I think some artists' lyrics have gotten better. As a medium, hip-hop still has a lot of evolving to do. Yet it has empowered young people, it has created jobs—from clothing lines to the movies—and it has given our youth more joy and hope and a better form of release than almost anything out there. Yes, there are negatives. But hip-hop has saved lives.
Oprah: When you're producing an album, is there ever any discussion about the lyrics?
Sean: Yes, I talk to my artists. I lost my best friend, Biggie. He was shot. His albums were called Ready to Die and Life After Death. One of his album covers was shot in a cemetery. Anything I've ever put in a record, I've seen it come true. So I try to teach the artists. I might ask, "Is that really worth saying?"
Oprah: So your sense of responsibility has evolved.
Sean: Yes, and I think a lot of our senses have. Don't forget: Rap is still an early and imperfect art. If you put a magnifying glass on everything most of us did at age 18, not a lot of us would be proud. To grow up, hip-hop needs help from its elders. It's best to keep the conversation open. We come from a generation of children who weren't really talked to. We were just thrown out there.
Oprah: I agree. I feel that my generation of black people really failed our children. We didn't teach you to appreciate the price that had been paid for our freedom.
Sean: I have to say we feel that. And we're not mad or bitter about it....
Oprah: I think y'all are!
Sean: I think we've moved on. We're just doing the best we can.
Oprah: As an elder, I have such a problem with the N word. I was down in Mississippi yesterday, and when people there use the N word—no matter how many times rap has tried to make the word okay—it's still derogatory.
Sean: We're clear with that. But we don't use the word in that way. For us, it's an endearing term. I know it might sound crazy.
Oprah: It does sound crazy. Black people beat their children because the slave masters beat them. We took the habits of the slave master, and we destroyed our children in many ways. The N word was the slave master's terminology for us. I know that's an elder's point of view. I'm just asking you to consider that the N word was the last word every black man heard as he was being lynched.
Sean: I will consider it. I just want you to understand that when we use the word, there's no malice in it.
Oprah: I do understand. I just don't want whites to ever think it's okay to use that word. So let's move on. What's your favorite meal?
Sean: Breakfast. French toast, scrambled eggs with cheese, turkey bacon.
Oprah: That's Gayle King's menu. Do you like to cook?
Sean: Yes, and breakfast is my specialty. One day I'll make you breakfast.
Oprah: When you opened your Sean John store on Fifth Avenue, what did that feel like?
Sean: It felt like black history. You see, our generation really wants to make you all proud of us. That's the craziest thing about it. We want to know that we're doing a good job. We look up to you.
Oprah: Opening on Fifth Avenue was huge.
Sean: Yes. The same year the store opened, I won a "menswear designer of the year" award. Something that began as a hip-hop brand is now a globally recognized brand. We've proved that black designers can be successful.
Oprah: Have you always loved fashion?
Sean: Yes, and I was blessed with an eye for detail. I was also designing for a community that doesn't get serviced.
Oprah: Martin Luther King said not everybody can be famous, but everybody can be great—because greatness is determined by service. So my philosophy is that whatever you do, see it as service. It will be much more meaningful and powerful.
Sean: It's about giving. I think that's why we're put on this earth. I also learned that from talking to Russell Simmons. He has a way of talking without preaching at you.
Oprah: I just had a lightbulb moment—that rap...it's kids who suddenly became really successful. It's like the first time you get a whole lot of money. You're not sure what to do with it.
Sean: We go spend it. But now we're learning about annuities and portfolios. It's my fault that there's a misperception of who I am: People think all I do is party and buy diamonds. But I do like nice things and I make no apologies for that.
Oprah: How big is your closet?
Sean: I have rooms, not closets.
Oprah: Do you look forward to getting dressed up, or is there some anxiety?
Sean: I don't get anxiety. It's fun. I love being dressed in a suit. I love being clean. I love looking good for my girl.
Oprah: What do you hope your legacy will be?
Sean: I hope I'll be remembered as someone who worked hard. I hope I leave an understanding, especially to my people, of what it takes to achieve your dreams. The playing field is not even for us, and I have no problem with that because I think we're built for it. We went through slavery so that we could withstand the challenge. I take pride in the trend of entrepreneurship in our community.
Oprah: You have a new album. What's distinct about it?
Sean: This album contains much more musicality than my others. My motive was to put out the best music I could, not necessarily to sell millions of records. I've been number one a lot, and that's great. The vibe of this album is about giving. I think if you believe in giving, then you know it will come back to you.
Oprah: What kind of father would your children [Justin, 12, and Christian, 8] say you are?
Sean: They would say I'm fun to be with. On the flip side, they would say that I'm very busy.
Oprah: Do you spend a lot of time with them?
Sean: Not as much as I'm going to and as I should. I know what's waiting for them out there, so I want to be sure they're ready. I also have to give credit to the two mothers of my children [Justin's mother is Misa Hylton-Brim; Christian's is Kim]. They are both amazing. We have a partnership in raising them. That's why they're incredible, pleasant, charming kids. My children are my proudest moment. Like me, they're chameleons, as comfortable in the Hamptons as they are in the streets of Harlem.
Oprah: Will you and Kim ever marry?
Sean: If I marry anybody, it will be Kim.
Oprah: How many times have you been in love—that heart-skips-a-beat kind of love when you're on the phone for hours?
Sean: Four times. But I've never had a friend like Kim. Being "in love" and having all those good feelings doesn't mean the relationship will last.
Oprah: Were you in love with Jennifer Lopez?
Sean: Yes. Jennifer and I are so much alike as far as our drive, our determination, what we want to achieve. That's why we connected. But I could never go forward and finish the relationship with Jennifer because I was still in love with Kim. She still had my heart. Now there's an Oprah revelation! You should have me lying back on this couch.
Oprah: Do you and Jennifer remain friends?
Sean: We're cool. But to be fair to the ones we love now, it's best that we remain friends from a distance. With Kim, I ain't got no more strikes. I can't play around. Whenever I see Kim, I still get excited. If I walk into a room and I know she's there, I'm either smiling or acting like I'm not smiling. I still feel nervous around her.
Oprah: Would you say she has been through a lot with you?
Sean: Definitely. Kim is also very intelligent. During the whole Jennifer Lopez thing, she was like, "You'll be back. Go do your thing, silly boy." I'm quite sure that was a tough time for her, but she was cool as ice. That's sexy!
Oprah: What kind of relationship do you have with your mom?
Sean: My mother likes to spend time with me. She loves me so much, and she's so proud of me. She almost killed herself to make sure I went to private schools, to expose me to travel. She made sure I never looked down on other people. She also ignited a fire in me.
Oprah: She's like legions of courageous black women.
Sean: She wanted me to be bigger than my circumstances. During the trial, she walked by me every step of the way.
Oprah: What is the purpose of your power?
Sean: To inspire others and to show people what is possible. I want my life to be about more than just fame or jewelry or parties. Hip-hop has the power to change the world. I am here to lead by example.