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.