Sean Penn grew up amid great privilege, said Mark Binelli in Rolling Stone, but he ran with a violent crowd. The 48-year-old actor—whose father was the director Leo Penn—spent his teen years on the beach in Malibu, Calif., with a rough bunch of surfers. A startling number of them came to bad ends. “It was a combination of Huck Finn and Rumble Fish,” he says. “There was a culture of what I’d call soft violence, in the sense that we didn’t let outside surfers surf our beach. We beat people up. This group of surfers, in some kind of Lord of the Flies way, found reasons to put their lives into situations that were horrifying.”

Many of them, Penn says, landed in jail—if they were lucky. “One intentionally ran over somebody with his car. There was one guy we surfed Zuma Beach with. We took a bunch of Quaaludes before we went out and he just drifted off into the ocean, and nobody ever found him. Another guy I surfed and played Little League with, he was dealing and doing blow and shot himself off the edge of a cliff in a car. Another guy killed his mother.”

Penn’s exposure to the darker side of human nature may have helped inform his work as an actor, but many of his old buddies got nothing out of their escapades but early deaths. “Some people are kind of shocked by this, but 10 of the guys I grew up with are dead. That’s a big number.”