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.