Howard Stern's Long Struggle and Neurotic Triumph

'If you want to go to the next level, you gotta open up a whole bunch more. That's the secret for anybody who's considering a career in radio'

Howard Stern
Photograph by Mark Seliger
Howard Stern on the cover of Rolling Stone
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"Do you have a big, thick penis?" Howard Stern asks a guest in his New York radio studio one recent Thursday morning.

The guest, unfortunately, is me.

The Howard Stern wing of the SiriusXM headquarters in New York is not just a corridor of offices and studios: It's a combat zone. As soon as you cross the threshold, you are fair game. Employees with audio recorders and video cameras roam the halls, tasked with providing 24/7 content. Meanwhile, writers and producers dash in and out of doors like a Warner Bros, cartoon, gathering clips, news, jokes and callers for the radio show.

Inside the studio, Stern sits, weary and all-powerful, on his self-made throne, surrounded by a massive three-sided desk, a mixing console littered with sheaves of paper and at least five computer monitors that all but block him from view. His support team is almost completely isolated from him: Sidekick Robin Quivers is encased in glass on the other side of the studio, while his longtime sound-effects man, Fred Norris, is hidden behind a partition on his left. His guests, meanwhile, sit unprotected on a red couch, vulnerable and flanked by Stern staff. Every element of the room has been designed to remind you that this is Stern's kingdom, and if you're not an adviser to the king, then you're his court jester.

I had come to the studio to observe the show, after which Stern would be conducting the Rolling Stone interview. But instead, I ended up as the jester, blitzed with question after question for over an hour until, finally, he had me divulging something to millions of listeners that I'd never even told my own girlfriend – and would take several dozen roses and apologies to recover from.

And that is one reason why, after 35 years of broadcasting, Howard Stern is no longer just at the top of his field, he is in a league unto himself. When he left FM radio for Sirius satellite radio in 2006, detractors said that he was dooming himself to popular irrelevance. But instead, five years later, Stern, at age 57, looms as large in the popular consciousness as he ever has. And this is not just because he has almost single-handedly helped Sirius grow its subscribers to something approaching his listenership on terrestrial radio, but because he has thrived so long, so consistently and so successfully as one of media's most powerful outsiders that he has become an elder statesman. The term "shock jock," which used to be synonymous with his name, now seems like a quaintly anachronistic misnomer for someone more famous and smarter than nearly every guest he interviews, for someone who can go on the Late Show With David Letterman and tell the host how to run his own show, and for someone who can sit in a room and improvise four hours of comedy four days a week. Stern and his entourage, which includes the Howard 100 News team dedicated solely to covering its namesake, can be heard all day, every day, not just on two SiriusXM channels, but on his own subscription-cable channel, Howard TV.

Is this narcissistic personality disorder elevated to an art form? "I've asked many times, and I never got a diagnosis," he says, sitting in his office after the show. Then he adds, laughing, "But I'll be the best goddamn narcissist on the planet."

And so it was that, late last year, the self-anointed king of all media renewed his contract with SiriusXM for another five years and an estimated annual salary of $80 million, tempted to carry on by an app enabling listeners to hear him on mobile phones and by the mission of molding his channels into talk formats that will outlive him. But behind those challenges was a fear: the fear of stopping when he's just getting started.

When people ask how you get such good interviews, you always say it's your odd curiosity. But I realized while you were interviewing me that it's also because you have a limited attention span.
You're 100 percent correct. The biggest criticism of my interviews is that I cut people off. I think my biggest asset is that I cut people off. It sounds like a contradiction, but the fact is you can't allow people to drone on. You are the orchestra leader. You are the one who is saying, "My audience wants something new. I gotta keep it fresh." I don't want my guests to bomb. My analysis is that a good interviewer not only asks the right questions but has sort of an inherent sense of what's interesting to this mass audience. And I don't know if you can teach that anywhere.

So how did you get it?
My theory on that is that I used to sit in my parents' living room, and they would call me in to do impressions. I used to do impressions of all the mothers in the neighborhood. I'd get them rolling with laughter. But sometimes – and this is a terrible thing to do to a kid – my father would literally say, "Stop! You're going on too long. Shorten it up! Make it interesting!" In order to get my own parents' attention, I had to tighten up the story. So I'm awfully paranoid about droning on too long.

Outside of worrying about boring the audience, are you interested in hearing other people talk about themselves?
I don't think I am. In my real life, I have a hard time having a conversation with anybody. I have little patience for sitting there and listening to people, and I barely know how to socialize. It's weird. But I know when I'm doing good radio. When they hit the right mark, I know it. I can feel it. But I'm not a guy who walks around interested. I don't necessarily want to be at a party listening to you.

And I felt during the interview like I was dancing on a hot plate to keep the ringmaster entertained.
When you got into your girlfriend being dry sometimes [during sex], that's when I knew I hit a home run. You hit it, but I brought you there. I knew the audience was going out of their minds. I could sense them all with us. And I did my job.

How much calculating goes on in your head as you do the show?
When that show is on, I feel like I'm calculating everything. It's maddening. After the show, I come back to my office, I do Transcendental Meditation and I pass out. My head is on fire. I am completely drained. I used to wash dishes for a living. That was so much more enjoyable, doing physical labor, using your body. I just had my buddies, and life was simple. This, you fucking obsess over. I'm telling you, I was driving myself batty during the show today.

You kept looking over at me to see if you were being funny.
That was definitely going on, and I caught myself doing it as well. I realized I was watching to see your reaction to things. One person not laughing can make me insane, and there were a couple of times during the news where I thought I was really rolling, and I looked over and you were kind of just watching. You weren't laughing or anything. I went, "Oh, fuck, I'm not that funny today." It really fucked my head up.

There were parts that were really funny.
But I wasn't breaking you up. It was the worst feeling. I said, "Oh, stop looking over," but I couldn't stop myself. It's a horribly neurotic thing. In fact, I just signed this new contract with Sirius, but I really was considering leaving. I am sure, on some level, I enjoy doing the radio show every day. But the neurotic attention I devote to it and the inability to get rid of that insecurity is very fatiguing for me.

The curse is that I take it so seriously. I just can't walk out of here and say, "I did a good show today and I'm very satisfied." No, I gotta know, do you think I did a good show and are you satisfied? And that's the neurosis and that's the source of all problems for me.

That's why you can't connect to people, because if they're not talking about you or giving you feedback, you're not interested.
Because my own opinion doesn't matter. And why is that? Of course my opinion should matter, but it doesn't. Your opinion matters!

And because of that, you can pick up on what someone is feeling from cues that other people aren't even aware of.
The ability to interview people and read your subject comes from my mother being very demanding of me with one thing: that I should be able to read her mood and know what she wanted. I could look in my mother's eyes and know everything. When she was sad, when she was angry, what she was thinking. I was trained to make my mother happy. And I swear to you, when I sit there on the radio, I don't miss a trick because I'll study it. I count how many times you blink. You blink a lot, by the way. I watch everything.

If someone measured your brain-wave activity during the show, it would be interesting to see if your brain state changes.
Oh, my God! People who have seen me work – when I don't wear dark glasses and you can see my eyes – said my eyes go back and forth like a mile a minute. I said to my wife, "I'm in another zone." It's almost like my eyes roll into the back of my head, and four hours later, the show's over.

Do you ever fear your sharpness starting to deteriorate as you age?
Yeah, I guess I even questioned myself about signing a five-year deal. I go, "Gee, I wonder if I'm as quick or as sharp." And I think I am. When I'm done with this contract, I'll be 61 years old, and that sounds like the right age to leave. But who knows?

I noticed your studio is set up to keep you completely separated from everyone else.
I designed it that way. It's the perfect studio for me. My plan was to not interact with anyone or see them.

Are you highly critical of yourself?
We have that Celebrity Superfan Roundtable [during which Stern's famous fans discuss the show], and I was listening to it. It was so complimentary that my OCD kicks in and my neuroses, and I go, "Oh, my God, these people think I'm so good, and I'm going to have to get on the air Monday, and I'm not going to be able to do that for them again. And they're going to hate me." It's such insecurity.

One of the things you would think at this point in my life is that I would walk on Letterman as an elder statesman, someone who's been on the radio for 35 years and has done it all and really would not obsess about it. It drives me fucking crazy. I go nuts. You know, I'm in therapy now. I've been in it for some time. And I can't figure out why the obsession, like, why do I have to have everything perfect, why does it have to be the best appearance ever? The pressure I put on myself is horrible. It's excruciating. Everything is neurotic! And therapy has helped me with that.

In what way?
The goal is to walk off the Letterman show or walk out of my own show and go, "I really like the show today and what anyone else thought does not matter." Now, will I ever be able to do that? I doubt it. I wish I could. I hope before I die I'll walk out one day and feel that way.

Most people would think that a guy who spends four hours a day talking on the radio, the last thing he'd want to do is go talk about himself some more in therapy.
But it's not therapy. Talking on the radio is a performance. Even though it's pretty raw, what I do, and I do open up, it's still a performance. If you go to a therapy session, it's a whole 'nother level. It's been useful to me because I think it's just opened me up as a human being. I feel less like a detached robot. I actually feel human. I don't think I did before.

What made you start going to therapy in the first place?
Well, my first marriage was ending, and I was very confused by that. I knew there was a lot missing from my life: I was totally neurotic and sort of consumed with work. I took work as the most important thing and the only thing. I knew things weren't right, and I said, "Gee, where am I going to get some answers?" I had never been a guy to turn to religion, but then as my marriage was coming to an end, I needed help to explain it to my children and make sense of it all and communicate with them. Because once you are a divorced guy, being a father is a whole different bag.

What was the first session like for you?
It was really a very scary thing to me. I had never really opened up to someone. I never had conversations like that with another human being, let alone a man. And I never in a serious way thought about how I felt about anything. I was completely closed off from my feelings... I remember I started telling him stories like I was on the radio, and I'm laughing, and he goes, "Why are you laughing? It sounds very important to me. It's very sad, some of these things you're saying."

Because the show keeps you busy all day, I'm sure it's a distraction from the work you need to be doing for yourself.
My therapist was actually making the point that, why can't you admit you enjoy doing the radio show, because I was really going to leave to just keep my own sanity. And he was like, "There's the side of you that enjoys this and needs it." Because if I'm really the guy who doesn't want to be connected to the audience that way, why am I suddenly tweeting? Here I have a chance to be on my own and I'm busy connecting with the audience. So there is a side of me that needs this connection desperately and needs this acclaim and needs millions of people listening to me.

But isn't that like an addict speaking about a drug?
It is an addiction. You hit it right on the head. It's an addiction to people. I'm a people addict.

Is the addiction people or the attention and acclaim?
That's what an addiction to people is: attention, acclaim, validation. I think all of that is operating there. It's desperate.

It's like sex addiction. There's a hole inside that's being filled with that attention. And as soon as it wears off, you need another hit or a bigger hit.
Sex addiction, people addiction, it's the same thing. You're really afraid to be on your own. Listen, how much sex do you really think you need when it comes down to it? It's not about the sex. After my divorce, I realized, "Oh, wow, I can go have sex." And I was running around, picking up women. Then all of a sudden, it dawned on me that I really didn't need that much sex. I just wanted somebody with me every minute. I was using women as a surrogate mother. When I tapped into that, it suddenly/became very childish behavior. And really, was it so great fucking every night? They're using me for my fame, I'm using them for their beauty, and the whole fucking thing seemed empty.

Considering how much you seemed like this beast in a cage during your marriage, it was surprising that you didn't find the freedom satisfying.
It seemed more like a feeding frenzy than anything. I was in a frenzy. I had to grab everything and everyone. It was as if I was entitled to everything. I knew it was unhealthy: I'm not entitled to everything, I'm like everyone else.

I'm going to ask this only because you asked it to me on the air: How many people were you with in that period?
A lot. I was crazy. School nights are sacred to me. When I have the show the next day, I go to bed by 8:30, 9:00. And I was staying up until 10:00,10:30. Yeah, real wild, man. I wasn't completely out of control. But for me, it was like I had to get a woman that night. I was single for a period of, like, a year, I guess. Honestly, I don't really know how many women, but it was a considerable amount of women.

Over a hundred?
No, no, no. I wasn't that much of an animal. But for me it was a lot.

So did you rush back into a relationship because you couldn't be alone?
Some of it is that. I never thought I'd want to be married again. I thought that dating a bunch of different women would be the way to go. Be like a bee and pollinate every flower, and who cares whose feelings get hurt. This is my time, and I'm gonna grab the spoils like Genghis Khan.

Do you remember the first person you were with and if that was a letdown?
No, it wasn't a letdown at all. It was amazing. Don't forget, I'd been a faithful husband for 25 years, and I wasn't the cheating type. And my marriage ending blew my mind. I was upset that I failed and let down my family, my kids, my ex-wife. It all was very painful. But as far as being with somebody new, it certainly wasn't unpleasant. It was kind of exciting, but at some point, it became like I was on autopilot. I don't know what I was doing: I wasn't thinking of myself as a human being who valued myself. This sounds crazy to a 17-year-old boy sitting in his room saying, "Hey, man, fuck everyone." But it wasn't what it was all cracked up to be.

In what other ways?
It seemed really bad when you were with somebody and you're not that into them. And you're saying, "OK, I'm done with you," and throwing someone out with the garbage. I mean, I don't know how guys do it. It's not fair. And sure, for any guy, of course, if no one's feelings got hurt and you could just fuck everyone, that's great, but it just doesn't work that way.

That's why the Charlie Sheens get prostitutes.
I'm too germ-phobic.

Also, for you, I think it's not about just getting your rocks off, it's about being desired. That's the truth. Not feeling inside that you can value the radio show or the Letter-man appearance you've just done, but you need that woman to value you in order for you to feel valuable. That's the saddest life. It's the worst kind of life.

It's interesting, you choose not to have this life, yet you sell it on the radio show.
It's funny that people's perception of me is that I'm some sort of wild animal when, in fact, I'm interested in interviewing the wild animal because I am so controlled. I'm fascinated by the out-of-control guy or exploring the porn star who has completely defied her family, her morality and values. And I'm like, "Wow, tell me about that. How do you get to that point? Part of what you're saying I kind of admire, but then again, you're destroying yourself too."

I sort of admire Charlie Sheen's ability to say fuck you to the world. It's a fascinating car wreck because, you know, how many people are in Hollywood dying for a hit television show? I don't know whether to give him a medal or to throw him in a loony bin. He doesn't care, and that's not me. Oh, I care! I care what my parents think, I care what you think, I care too much. In a way, I'm in as weird a place as Charlie Sheen. He doesn't care at all and I care too much. Where's the middle ground?

I'm curious to do an exercise with you. Do you have any paper?
Where do I have a piece of paper? [Searches his office] You'd think a guy who walks around writing dick jokes all day would have a piece of paper [grabs a Post-it pad]. Can I do it on one of these little fuckers?

That works. Now go back to when you were between the ages of three and 12, and draw a graph of your immediate family: your mom, your dad, your sister and you. Make the men triangles and the women circles, and position them on the paper in terms of how emotionally close you felt each person was to each other.
So here's me on the graph, and here's my father. Here's my sister and my mother, and here's my emotional closeness. [He draws a triangle and a circle next to each other at the top of the paper, representing his parents. He then draws a circle representing his sister just below them. Then he draws himself as a tiny dot, all alone, in the bottom corner of the paper. As an afterthought, he draws a line connecting each shape – except his dot.]

That explains everything right there. That's your disconnection from people and your view of yourself as an outsider. That's your emotional DNA.
You see, my father was very emotionally cut off from me. He worked long hours, got home at about 7:00 and left early in the morning. I don't ever remember my father in my entire childhood saying, "How are you feeling?" or "How are you doing?" My father had no interest. I had some really interesting experiences as a kid growing up in an all-black neighborhood, and no one thought to ask me how I was handling it. It didn't matter what I thought, even emotionally. My mother and I had many conversations, but most of them were about her, her upbringing, her development and how I could please her. And my sister is great, but we were never emotionally close. So I think that a lot of my inability to get close with people is based on all of that. I was always an outsider.

Usually people draw themselves the same size as everyone else, but you made yourself a dot.
Oh, I was. I did that intentionally. It's almost humiliating to me because that's what I felt like. Like there's these two big circles and a triangle, and I'm down here. Notice they're all joined together by a line and I'm outside of it.

It's sad to me, because I adore my parents. My parents are still alive and I see them quite a bit, and they're terrific people and my biggest cheerleaders. But when I was young, I was very misunderstood and I was put into a lot of dangerous situations that they didn't really look into.

In terms of?
If you look up the neighborhood I grew up in, it's horrendous. It's such a bad neighborhood, and it was so disturbing to be one of the few white families left in the community. And my parents never came to me and discussed it. You would think all of your friends moving away within a period of a year – every friend you ever had – would be something that might be open for discussion. And yet I never complained about it to my parents. I never allowed myself to feel anything about it. I still don't know what I feel about it. Why didn't I feel comfortable enough to say, "I can't handle this"? Why did I want to be a hero and a martyr to my mother and father?

I think that's why now having the freedom to communicate freely and be heard is so important to you.
Yeah, maybe. It's weird. Until this day, I've only discussed this in therapy. I didn't become a racist because I said, "What's the difference, black or white, since whoever's in the majority seems to take it out on the other?" I certainly read in history of all the white mobs that would beat up black people and hang them and do terrible things. Suddenly I was caught up in just this. As people, we can all be so vicious. When I was in this community, at the drop of a hat someone could start yelling and screaming at you and you weren't sure why, and suddenly you're in a fight or being choked or punched – physically abused. The whole thing is very confusing to me, but more confusing is the dynamic of the graph you had me draw because I don't know how, as a parent, I wouldn't say to my kids, "Listen, this is too much for you to bear."

But when you finally moved to a white neighborhood, the same thing happened and you couldn't blame it on race anymore.
It turns out it wasn't race, it was me! I was the awkward one. I was like, "Oh, black people hate me." Then I'm like, "Wait a second, white people hate me too." I felt more alienated than ever.

So you turned to radio, where no one could see you.
When I was starting out, I came to the revelation that if I was going to go anywhere in radio, I can't be playing records. I said, "I can't rely on the Beatles or the Rolling Stones to get me ratings. Every asshole can play those. But if what I have to say was important, no one can replicate that."

There was also more of an aggression and competitiveness to your early shows.
Radio was everything. I had to win – at all costs, no holds barred. Not to sound like Charlie Sheen, but losing was not an option. I put in a lot of work on it. I listened to every show back on tape. I spent thousands of hours editing tapes, writing commercials, incorporating sound effects. I spent endless days and nights thinking about this and nothing else...

You know, I was watching Charlie Sheen's really interesting attempt at radio the other night, and the first show was sort of a train wreck, which Charlie even admits. And I said, "Oh, if I could have only produced that!" He had so many good things he could have done. Like, as I'm watching it, my mind is clicking, going, "Take the two girls, give them a lie-detector test. All right, call the press in and do your own press conference. Call up three of the madams, offer the girls money to come in, and the first whore who gets to the house wins $15,000." Boom, boom, boom. And you start to say, "Oh, my God, you can structure a show around all of this madness."

What are the plans for the next five years of your show?
I haven't really specified. When it came down to sort of figuring out what I was really after, I was pretty sure I was going to leave the radio. I thought I'd kind of done what I needed to do. I still enjoyed it, but I also found that I wanted time to do some other things. Right now, my schedule is pretty much the same as it always has been. And then as time rolls on, I'll probably do about three shows a week. I've been doing this for such a long time, and getting up at this time in the morning never gets easy. You never get used to it. The alarm went off this morning, and it was as if it was the first day I was doing it.

Do you ever want to bring guests on the show who are more in line with your current personal interests?
Well, sometimes, but I have to keep in my mind what type of show I'm doing and who my audience is. For three years I became obsessive about chess, so I would have had every chess expert on and blown out my entire audience. I became so obsessed with it that I pushed everything else to the side and treated chess like a job. Now I've stopped completely because I really needed to shift focus. Now my focus is a little bit of photography. I recognize that some things are just my things. I'm a quiet guy who can read books on organizing. I'm fascinated by organizing. I'll think about organizing all day. Now who the fuck wants to hear a show about organizing?

It's interesting how your hobbies are things like chess and photography, which, like radio, are about interacting and connecting with people but through the safety of another device that serves as a barrier.
That actually makes sense to me, because I definitely want to connect, but I don't want to connect fully. I want interaction but at a safe distance. I can only get so messy with people.

Because it's difficult for you to deal with other people's emotions?
That's right. You know, a lot of times it feels like too much of a burden. That's a part of my personality that I've actually been working on changing, and perhaps coming in a little bit closer. But for the most part, I think it's really accurate. I tend to choose things that keep me at a distance.

It does seem like you've befriended more of your guests and other people now than in the past.
Yeah, I have. That's a conscious decision on my part. I notice when I'm able to break through my fear and hesitancy and create some friendships, it really feels good. I missed a lot of that by not fully being human. It's hard, because I'm the first one to tend to shut down. I'm the type of guy who will invite you to my home and then all of a sudden I'll be angry you're at my house, like, "When can I be by myself?"

You're one of the most honest guys in media, yet there are certain areas of your life that you don't go into on the air.
I try to be really open and honest about the things I'm comfortable with. But some things, I'm not comfortable with. I was never really that comfortable discussing my divorce with the audience. My ex-wife isn't a bad person. She's a really good person and we have three great children, and that is such a private matter for me. If it was my matter alone, I would discuss it, but there are other people involved.

There are ways that it can be shared without bringing her into it, like discussing your own pain.
Yeah, absolutely. Divorce was so theoretical to me because no one in my family had really been divorced. My parents have been together for a million years. So this was all new to me. I was with my ex-wife since college, so it felt like such a failure. My children took it so hard. It's so complicated, and it's hard for me even to figure out at this point what went wrong and how things that were so good could go so bad. It's tough. I think I'll spend the rest of my life trying to analyze that.

So you still don't know the actual reasons behind the divorce?
No. I mean, I think I do. It fell apart for a lot of different reasons. It's just too fucking complicated. It's so raw and so personal. I'm so fucking honest that I'd rather just say to you, "I can't talk about it because I don't feel comfortable being this honest." I don't want to give you some bullshit.

I'd rather hear that than something that's not true.
It just sucks. I've had friends say it's as simplistic as "You were together too long." And I go, "No, I don't think that's accurate." I think there were a lot of stressors, especially with what I did for a living. And, man, you can really lose your mind. I'm pretty sure I was very confused.

Are there mistakes you made in your first marriage that you want to avoid in your relationship this time?
Oh, yeah, absolutely. In many ways, my marriage now is so easy, but I'm also aware that I could fuck things up very easily. I could start getting more into my work, and ignoring what's important to Beth. I'm awfully narcissistic, and I have to keep that in check. I can't be like King Tut sitting there and expect to be taken care of, because so many times we can turn our wives into mothers. Things changed when we got married. Not so much between us, but the way people treated her. Everyone before was like, "Oh, are you Howard Stern's blond bimbo that hangs out with him?" But suddenly, when we were married, it was like, "Oh, this is Howard's wife." And that was important to me. Part of the reason I got married was that I wanted Beth to understand how important she is and also how equal I feel she is to me.

Since your divorce, you also talk about your kids less on the air.
When they were younger I did, and I brought the kids on the air. As they got older, I'd say to them, "Are you interested in coming on the air?" I'd figure they'd want to go into radio or television or something. But no, they don't have that desire. They don't see it as an attractive thing to get on the air and discuss their lives. None of them are looking for the limelight.

Your daughter who was acting, she isn't pursuing that anymore?
No, she's not pursuing acting anymore. In fact, she's studying religion now. Very serious about it. One of my daughters lives in San Francisco. She's working in the school systems there. My youngest daughter is going off to college. They're all very good students. I'm very proud of them. They're great kids, but, again, it's their lives and they're not comfortable being spoken about. So as good as some of the things that have happened in my life with my children are, in terms of radio material, I found somehow the strength to say no to that, and not be the guy who has to expose himself all the time.

At the same time, you broke through in the Eighties and Nineties by saying yes to exposing things when your instinct was to stop yourself.
I was a slug, and I was down in the mud. I felt very defensive. I had to do whatever I had to do to make a living, and I would tear the fucking head off of anyone who got in my way. And now I'm more comfortable with my place and what I've done. I don't feel as threatened by anybody else. I have a really nice friendship with Jimmy Kimmel. Years ago, I could have had a friendship with anybody in show business, and I didn't, because everyone was a competitor. Someone would say something about me, and rather than consider it, I would just blow up and start screaming, which to me is boring. Now that I look back on it, I wouldn't approach it that way. I would really stop, take a breath and go, "OK, what are they saying? Is there any truth to it? And why am I afraid to respond to it?" Now I'd be more likely to really deal with it in a more honest way. That's more interesting radio than the knee-jerk I'm gonna scream and yell and just fight.

The other thing you don't go into on the air is money and your lifestyle.
I get uncomfortable about that. Maybe because I can be so envious of money and power and fame and stuff that I'm sensitive to the guy who doesn't have it.

On air, you talk about your house on Long Island instead of the Hamptons. Is it because you want to be relatable?
I'm very self-conscious about it because I grew up on Long Island, but I never heard of the Hamptons. Where I lived, it wasn't the beautiful Long Island; it was horrible. And there's a part of me that still feels connected to the guy who doesn't have that stuff... I never got into it for money, so I became uncomfortable when all of a sudden there was a shift where I was now in the business section as opposed to the entertainment section.

What do you do with the money?
I'm very conservative. I'm not a guy who spends a lot of money on himself. I don't think it's a cheapness; it's just a respect for money. I got that from my father. I have stocks. I have some bonds. That's it. I'm not very sophisticated about that. I've read horrible things about people who make money and go out and buy an entire wardrobe and never wear the stuff. They buy crazy things, multiple cars.

The other thing you haven't discussed much are your feelings about Artie Lange.
It's OK to bring that up... Finding Artie was a great joy. But Artie's demons got ahold of him, and I'm probably the last one to really have realized what he was going through. To me, Artie was coming in and doing his job and he did it so well that I really didn't think he had a problem. Toward the end, I got it. You'd have to be blind not to see it. But I'm not a drug guy, really. Early in my life, I took drugs, but I'm very naive about it. Maybe I just wanted to have blinders on, I don't know.

In fact, we were due for a vacation, and Artie took a few days off beforehand because things were getting really bad for him. He was getting into a real depression. And you know what happened: He tried to kill himself. I've spoken to Artie a couple of times, and I think he's going through a real big struggle right now. The reason I don't bring up his struggles on the air is that I feel, again, it's a private family matter for Artie. I really feel kind of dumb that I didn't pick up on the signals. And Artie has even said to me recently that he would be willing to come on the show and explain what happened and stuff, and I don't even feel strong enough within myself or that I'd be doing the right thing by him, because I don't want to do the wrong thing for Artie. I just want Artie to stay alive.

While there are some things you don't discuss on the air now, at the same time you're a lot more open-minded than you used to be.
You know, people have said to me, "Gee, your show has gotten better. It seems multidimensional." I think it is because I am actually curious about other people's feelings. Therapy has opened up new sides to me. I'm more willing to explore areas that I didn't understand before with people. I was more one-dimensional, like Cro-Magnon in a way, banging people over the head in my early years. Sometimes when I hear the old shows broadcast, I want to cringe.

It actually seems like you've broadened your base now.
The sad part in it for me is that not everyone has Sirius. Instead of looking at the good – we started out with 600,000 people five years ago, and now we're at a company where we have 20 million and growing – I go, "But what about the guys who don't have Sirius?" And that is why I got excited about the new smartphone app, because all of a sudden, now it's like when the transistor radio came out. For a long time, people couldn't travel with us. Thank God for this technology. You can go to your gym now and hear the show. You can plug the phone into your car. The show is as accessible now, I feel, as it was on terrestrial radio. This is a game – changer for satellite.

Some fans get mad that you've changed, but those same people that got mad would also get bored if you stayed the same.
Absolutely. I get angry with performers like Rush Limbaugh who are just shills for the Republican Party. I'm not a big listener of his, but wouldn't he be a lot more interesting if once in a while he was for something that the Republican Party was against? I thought he had a real opportunity with that whole drug-addiction thing to maybe open up and say, "Man, I'm as confused as all of you." But, no, he has to keep the persona. He's an expert. He knows everything. It's boring. You've gotta grow. The audience has to feel that growth. There are so many guys doing the same act, like Sean Hannity. If Limbaugh was the one guy who started talking about his insecurities, then he'd have a following that would be 10 times the size. If you want to go to the next level, you gotta open up a whole bunch more. That's the secret for anybody who's considering a career in radio.

Some of your shows were eerily prophetic, especially when you're telling celebrities what's going to happen in their careers.
Those shows can bite you in the ass, too, because I think the war in Iraq is ridiculous, but you can hear old shows of me screaming, "Come on, we have to go to Iraq and blow everyone up." Oh, fuck, I sounded like an idiot.

When I pointed out how prophetic you were, your first instinct was to point out the times when you were wrong.
You're right, I tend to go to the ones where I was completely wrong, and I shudder to think how many of those are out there.

If you look at your life now, you're on radio and TV 24/7 You have a beautiful wife. You've succeeded in all your goals and are paid better than almost everyone, and yet you're still not happy. What would it take to make you happy?
I don't know. That's so complicated. There is an anger inside of me. Once in a while, I can douse it with some water, but it just never goes away. I don't know how to get rid of that.

Where do you think that anger came from?
I had something to prove to the world, to my father, to every woman that never fucked me. You know, everything. It was all over the place. I'm not saying I'm fully evolved now. I'm not Buddha. Sometimes it's hard for me to accept that I don't have every listener and I haven't written every good joke. I get competitive. But that's no way to live. I'm tired of walking around angry. It's a burden. And that's why I'm trying to find balance.

So what's the brass ring for you now?
Years ago, I would have answered to do another movie, or this or that thing. I'm not sure how to answer that. The brass ring is to actually find some balance. The whole idea of balance is to live with that anger or understand it, and somehow it dissipates. But I don't know if you ever get rid of it. I think that would be beautiful, but I don't know what it would take.

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This story is from the March 31, 2011 issue of Rolling Stone.

From The Archives Issue 1127: March 31, 2011
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