Howard Stern's New Challenge

This story originally aired on Dec. 4, 2005.

Love him or hate him, you can't deny his success. Over the last 20 years, 52-year-old Howard Stern and his raunchy, adolescent male humor have changed the face of morning radio and made him number one, with as many as 22 million listeners a day during his heyday, most of them men.

But Stern has also been the subject of more fines for indecency by the Federal Communications Commission (FCC) than any other broadcaster in the history of radio.

When correspondent Ed Bradley spent some time with Stern last Fall, he was facing the biggest challenge of his career: a move to Sirius satellite radio, which operates without the restrictions of the FCC. Stern had signed a $500 million five-year contract that pays his salary and the costs of doing there, starting last January, what he did on free radio: entertain millions while offending millions.

He's on the air five days a week, more than four hours a day. Part animal house, part madhouse, part cathouse, his show is a steady stream of Stern's consciousness about anything going on in Stern's mind and life, appalling to some and addictive to others.

Stern is unrepentant about the material he has been fined, censored and criticized for, unrepentant about the incessant chatter about sex and excrement, the racial and gender stereotyping, and the vicious attacks on his perceived enemies, like one in 1992, when he talked about former FCC Commissioner Alfred Sikes.

"I pray that his prostate cancer spreads into his lungs and his kidneys. I pray to you Jesus, answer my prayer," Stern said on his program about Sikes.

"Yes. But that is me being outrageous," Stern explains. "I don't know that I would do that now. I'm older. But I don't have to apologize for that. I'm on the air five hours, and I blurt out anything in my head. Dangerous? Maybe. You know, do I say things afterwards that I regret? No, because those are the thoughts in my head, and I share them with the audience."

"Let me ask you something. Did you ever wish anyone dead?" Stern asked Bradley.

"Maybe as a kid," Bradley replied.

"Okay, well, I guess I'm still a kid. Because when I get really angry and fired up and I feel like my back is up against the wall, I will say vicious things," Stern said. "And rather than hide that, I would rather put that out on the radio and let someone see the full range of emotions. If you're going to be strong on the radio, you got to let it all out, even the ugly stuff. And you can't apologize for it."

But you may have to pay for it. The FCC has fined stations that carry Stern almost $3 million.

Did the FCC win and get rid of Stern?

"You could choose to look at it that way. I don't. I look at it that I won. I go to a new medium. I'm uncensored. And for me, it's a checkmate," says Stern.

Manhattan-based Sirius has more than two million subscribers who have bought a satellite radio and pay $12.95 a month to listen to more than 120 channels of music and talk. The content is not regulated by the FCC.

Does that mean there will be more profanity and more explicit sexual content?

"I think so. I look forward to exploring that. I don't – you know, listen – I'm about being funny. If I can make a joke using profanity, I will. But for the most part, that can get awfully old and boring. You've got to know, you've got to draw your own personal line. This is a new frontier," says Stern.

Stern says there is a line he won't cross. "There are things that I won't do on the radio. I mean, the next logical question is, what won't you do. I say, well, you know, you've got to find out when you're on the air."

Stern will have two 24-hour channels that will air his radio show, as well as other programming he's developing, that he says will be "Howard-centric."

Does Stern think his audience wants to hear all-Howard, all the time?

"No, they're not going to hear all things about Howard. It's going to be programming with my sensibility. It will be outrageous," explains Stern. "We have a woman, for example, who's starting a show this week. Her name is Heidi Cortez and she is very good at phone sex. And her job is to put the audience to sleep at night, and she will have phone sex for a half hour with a member of the audience. And it's called Tissue Time with Heidi Cortez."

"Howard, you're sick," Bradley said.

"I'm a sick man, Ed," Stern replied.

To understand Howard Stern, it helps to go back to Roosevelt, Long Island, where he grew up, he says, never feeling good enough. He was raised by his mother Ray, a housewife, and his father Ben, a radio engineer. Stern talks to them regularly today, and they are often guests on his show.

Stern says being a good performer was highly valued in his family. "My father would sit there and if I started to tell a story, he'd go like this, 'Quick, quick. C'mon. Move quicker. Move quicker. Move quicker. You're going too slow.'"

Stern says his father was distant.

"My mother, yeah, it was a different kind of relationship. My mother was very involved with me. And we had a dialogue constantly. And it was like an umbilical cord. As long as the words were flowing back and forth we were connected and feeding each other. And I probably grew up very afraid of losing that connection," says Stern.

So afraid that, Stern says, he never once asked to leave when his friends moved away in the late 1960s, as Roosevelt changed from mostly white to mostly black. The Sterns stayed until he was in high school because his mother believed in integration.

He hadn't been back to Roosevelt since then and on a visit with 60 Minutes, Stern said none of it looked familiar.

"I grew up here, but I really kind of blocked it out. I'm realizing that now. I'm just a little confused," Stern said.

"Oh my God, I don't even believe, that's my house! I can't believe that! Yeah, that's where I grew up. Holy mackerel! I call it the house of horrors," Stern said. "It was horrible. It was a horrible place to live. This town was a horrible place to live. It was a nightmare."

Stern says it was a nightmare because he was a minority. And that, Stern says, left him isolated and alone.

"My mother wanted to prove a point. My mother said, 'We cannot run from black people.' But the problem was, my mom stayed in the house all day, and she sent me into Roosevelt High School. And I had a whole different experience. I was a kid and I had to fend for myself. I mean, I'd be sitting in a classroom and a guy would just turn around and bam, punch me right in the face," says Stern.

Why was Stern attacked right in the classroom?

"For being white, or just, for whatever. For anger. I mean, these kids were angry, man," says Stern.

Stern says there were lessons he learned growing up in Roosevelt. "Oh my God. It's the way I relate to the world. There's a general distrust. There's a lot of fear. There's also a tremendous sense of humor too," says Stern. "But really what stuck with me was the hypocrisy. I could never get my mind around the fact that all those white people left. It pissed me off, and I think I felt very left behind. And I suppose I'm angry about being the one who got left behind. To be the odd man out is not easy."

But on the radio, Stern is the odd-man in, the person who controls the show, who decides what material gets used and who gets on the air.

"I think when you listen to me, you're an insider. You're in the club. We're not the guy in Roosevelt High School being goofed on when we're all together. We're strong. We're together. Some of us are misfits. Some of us are outcasts. And we can admit our insecurities and we can laugh about them and have a great time," says Stern.

On his show, he is surrounded by a loyal staff who help him create the intimacy of an out-of-control, free-wheeling locker room.

Co-host Robin Quivers, writer and sound effects maestro Fred Norris and show producer Gary Dell'Abate, have all been with Stern for more than 20 years, are moving with him to satellite with the rest of the staff.

But despite the comraderie, Stern admits that he's hard to work for.

"I'm not a good listener some times. I'm too much of a control freak. I'm learning to be better. I was so caught up in just getting the job done that I would miss out on the human aspect of this. There was a connection missing. But I truly love those people I work with. And I appreciate everything they do for me. And I just don't say it enough," says Stern.

It's something he gets emotional about. "Yeah, I do. I really feel that I could have been more connected to them," says Stern.

Stern says his inability to connect with those close to him off the air is an ongoing problem and one of the reasons for his divorce in 2001, after 21 years of marriage to the mother of his three daughters.

"I am withdrawn. I have a hard time sitting and relaxing with people and appreciating how much fun that can be. In some way I'm very self-contained, but I think again that's control. Long as I'm working and doing my thing, I don't have to deal with anything or anyone else," says Stern.

Perhaps Stern's most intimate connection is on the air, with his audience.

"The one thing that I do know is that when I get behind that microphone and hit that button, it's about as good as it gets for me. That I can sit there and feel the guy at the end of the radio and know he's with me. And I know I'm making him laugh. And it's just perfect. It's great. It's a wonderful rush," says Stern.

Stern says he is making some progress on the relationship front. Today, he lives in Manhattan with Beth Ostrosky, a 33-year-old model from Pittsburgh whom he met five years ago.

She told 60 Minutes her mother wasn't very happy about it.

"My mother is a super conservative Catholic woman who…" Ostrosky began to explain, when Stern chimed in.

"This is great. We - so - just real quick. She, we," he interrupted.

"You've got to control her story?" Bradley asked.

"Okay, I'm sorry," Stern apologized.

"No, this is good. That's, I…" Ostrosky continued.

"Yeah, I do. This happens all the time," Stern said.

"So I met Howard at a dinner party. I called home and I said, 'Mom, I met the most amazing man.' And she was so excited for me. And I mentioned who it was. She hung up the phone. She went to church. And she didn't talk to me for two weeks," says Ostrosky.

Stern told Bradley that three months into this relationship, Ostrosky had told him, "Howard, this relationship is all about you."

"Oh, I think I knew that from day one. But I'm okay with it. It's all about him, Ed. We watch TV, what he wants to watch. We eat. We wake up at five o'clock in the morning. We go to bed at eight. We, I love it, though. It's my life," she says.

But Stern doesn't really feel it's all about him. "Just 97 percent of it," he says.

But the radio and his audience are still the most important things in his life, Stern says, and the move to satellite is the last challenge of his professional career. It's a gamble: will people be willing to pay for radio, or will Stern fade into obscurity? Stern says he's obsessed with making it work.

"I think I'm probably a little too desperate to be successful," he says.

But he is successful, having just signed a half-billion dollar, five-year contract.

"That will never mean a thing to me. I will never feel successful," Stern says.

"Howard, you've had a successful book. A successful movie. A successful DVD. A successful radio program. Number one in I don't know how many markets. You've changed morning radio. And now you're going to satellite radio for a half a billion dollars over the next five years. You're not successful?" Bradley asked.

"When you put it that way, of course that seems successful. But when I'm up at two o'clock in the morning and I'm sitting and creating these two new channels, there's a fire in me that says, 'Oh my God. I can't disappoint that audience,' regardless of what they pay me," says Stern. "And maybe that's why I get paid a lot of money. When you hire me, you hire a nut who is going to work 24 hours a day for you and never, ever burn his audience."