Jay-Z: I never understood that saying. Because thieves, you know—
Oprah: They're thieves.
Jay-Z: They're thieves.
Oprah: You can't trust them.
Jay-Z: Right. But in the streets there's a certain respect level. If two drug dealers make it to a certain level, they show a certain respect when they see each other. It's bad business for them to be warring.
Oprah: Meaning there's a hierarchy on the streets.
Jay-Z: Of course.
Oprah: Well, how did you decide to leave the streets for good? How did you decide you could let it go?
Jay-Z: I started seeing people go to jail and get killed, and the light slowly came on. I was like, "This life has no good ending."
Oprah: That is so fascinating to me. Because what crack did to the community—drug dealers were a part of that. When you were dealing, did you not see yourself as a part of the problem?
Jay-Z: Later. Looking back. Not while I was in it. I didn't know the effect it was having on the community. We used to say all the time, "Man, her life is all messed up—she used to be so cute. She was fine six months ago. Look at her, she's finished." But you never thought you contributed to that.
Oprah: How is that possible?
Jay-Z: You're just in it. So deep in it, and so young, that that type of introspection never happens. It's just living. And it's fast.
Oprah: Looking back on that time, do you have regrets?
Jay-Z: Well, any person is responsible for the knowledge that they know, right? So of course I do—now, knowing. But at the time I had no knowledge of it.
Oprah: It was just a way of life. A way of survival.
Jay-Z: To be honest, I can't even say that. At that point it was beyond survival. I was successful. It wasn't like I was doing it to feed my family anymore. I was buying cars and jewelry and things like that. I had become addicted to the lifestyle.
Oprah: So how old were you when you realized that the life had no good ending?
Jay-Z: Around 20. I'd been trying to transition from the streets to the music business, but I would make demos and then quit for six months. And I started to realize that I couldn't be successful until I let the street life go. My mom always taught me—you know, little boys listen to their moms too much—that whatever you put into something is what you're going to get out of it. I had to fully let go of what I was doing before for the music to be successful. That was a leap of faith for me. I said, "I have to give this everything."