Howard Stern will forever loom large in radio history as the medium’s bawdiest personality, a man whose hugely popular shock-jock antics during the 1980s and ’90s spawned a legion of drive-time loudmouths. Since moving from terrestrial to satellite radio in 2005, though, he has altered his legacy in ways that only an especially optimistic oracle might have foreseen. Stern, 65, has gradually become a master interviewer, one consistently able to elicit honest emotion and genuine insight from his celebrity guests. His first new book in more than 20 years, “Howard Stern Comes Again,” showcases this transformation and his refined conversational style. “I had interviewed every porn star about every orifice,” Stern says of his wilder days. “Don’t get me wrong, I was fascinated, but I couldn’t be that guy anymore.”

You used to be known for doing these antagonistic celebrity interviews, which you now say made for bad radio. But as much as you feel embarrassed by those old snotty interviews, would you trade having done them for the type of interviews you do now? Your old style is part of what made you rich and famous. It’s not that the interviews I was doing were bad radio.1 It’s that they weren’t real interviews. They weren’t me learning about anybody. If I had allowed someone to give a thoughtful answer on terrestrial radio, within five words I would have thought my audience was tuning out. So I just blurted stuff. I had always wanted to do interviews that had substance. The problem was that, in the old format, you couldn’t.2

Did you ever try? You’re right, I never tried. You know, back then I loved Gilda Radner,3 and so when she went running out of the studio because I was a madman, I felt bad. By going into therapy I developed empathy and began to care about the fact that I was a fan of some people. I can’t tell you how obscured that information was from me. There was this disconnect. I loved Led Zeppelin, but I’d go on the radio and tear them a new [expletive]. I was in this negative space. I’m still that guy who will go on the air and blast whatever I think is horrible, but I’ll also allow myself to be a fan.

Was there a “eureka” moment when you understood that you wanted to talk to your guests in a different way? I wouldn’t say there was one moment where I went, “I’m done with this [expletive].” It was part of opening up in therapy. Before, I had closed myself off to everyone. Then I started to get off on the fact that when I talked to these people, they had had similar experiences to mine. I was feeling that there was something to be learned.

Your current interviews are almost always biographically driven. Are you ever interested in someone’s thoughts about politics or the world beyond their immediate lived experience? It’s not that I’m not interested. I’ll give you an example. I was interviewing Def Leppard the other day. The drummer who lost his arm, Rick Allen — before he walked in I was like, I don’t know what his sensitivity is with the arm. But I didn’t want to ignore the fact that this horrible thing happened to him. You’re a drummer, and you have one arm! How do you overcome that? So at the appropriate moment we got into it, and afterward he said: “Thank you. No one has ever talked to me about this in this way.” That is more interesting to me than whether or not he voted for Trump.

Twenty years ago you definitely would’ve found a way to turn an interview with a one-armed drummer into a bunch of masturbation jokes. Well, maybe. I didn’t give a [expletive] about that, because I jerk off with one hand, too. Come to think of it, one hand works the iPad and the other jerks off. Or one hand holds the tissue over the iPad camera, because I’m paranoid. But my point is that I try to hit all the bases. You could still ask your masturbation question, but with class.

Stern on WNBC radio in 1983. Fred Hermansky/NBC, via Getty Images

When your interviews were more hostile, they fit with the image you played up of yourself as a Hollywood outsider. But a lot of times outsiders badly want to be on the inside. Was that the case for you? Absolutely. The way I was when I was younger was somewhat dishonest. It has been an evolution. If I hadn’t evolved, I’d now be doing “Butt Bongo Fiesta”4 for guys in their 60s.

Has your thinking about women evolved, too? As you get older, you start to think about family and what their impressions might be. My daughters and my wife are so important, and I really did want to make changes as I got older in terms of what I put out there.

In Stuttering John’s5 book he says the show now has rules about who’s allowed to be made fun of. Is that true? John hasn’t worked for me for I don’t know how many years. I don’t know how he gets his information.

Is that true, though? No. There are people that I have spoken ill of, whom I’ve since called up and apologized to, and I don’t re-air those things.

Whom have you apologized to? Rosie O’Donnell. I was brutal,6 and at some point I realized how much I admired her. She’s a fabulous comic, she’s brilliant, and I began to develop a relationship with her. I said on the air that she’s brave, which was hard for me to do because I spent so many years bashing this woman. She had gone through so much [expletive], because when I go after someone, my audience goes with me. But we’ve developed this nice friendship, so I said to my guys that I don’t want to re-air me bashing Rosie.

Here’s another question about a former colleague: Is there ever a possibility of Artie Lange coming back on the show? It has been such a clean break. I choose my words about Artie carefully, because I love him.7 What’s happening with Artie makes me very sad. We’ve lost touch, and that’s my doing. I got my fingers crossed for the guy. And it wasn’t a clean break. It was many years of wanting Artie to get help. I know that a lot of fans want me to talk about Artie and feel it’s a cop-out for me not to. I’ll take that. I don’t want to do anything that would rock his boat. I get sad talking about Artie. He was a tremendous contributor. But we had to move on.

Donald Trump used to be a regular guest on the show, but he never got the serious interview treatment. Is he capable of the introspection that you want from an interview subject? No. I think I could get something out of Donald that is entertaining, but interesting? When I used to interview Trump, he was fantastic, because here was a real estate developer who wanted to be famous. He was as unguarded as any human being has ever been on my show. But once Donald Trump became a candidate for real — not like the couple of times he toyed with running — he became one of the worst radio guests. He had to. So now it would be a much different interview. But I would love to interview Donald and find out what’s going on with the marriage and Melania or how you fire a General Kelly. But could I crack him open and get my old Donald back? I don’t know.

Stern with Donald Trump at Trump’s 1993 wedding, to Marla Maples. The Life Picture Collection/Getty Images

It’s more that I’m wondering — and maybe this sounds corny — if you think he’s actually capable of a certain level of soulful introspection. No, I don’t. Donald is a well-guarded personality. I think he’s actually so emotional that somewhere along the line he had to close it off. That’s a valuable technique for people who have been traumatized. Donald has been traumatized, make no mistake. I believe his father was a very difficult guy. My theory about Donald, having spent some time with him — don’t forget Donald was at my wedding, and I was at one of his — is that deep down he did not want to be President. It was a publicity stunt. These are my beliefs based on facts that I know.

Facts like what? I know people who orchestrated some of these things. I was at Mar-a-Lago around when it was announced that Donald was going to run for president, and like everyone else, I thought, Ha-ha-ha. So, knowing Donald, I can tell you with some assurance that I don’t believe that he thought anyone would buy in. Lo and behold, people did. But I’m pretty sure that there was no intention of actually being president. Now as far as your question about a truly introspective Donald, I don’t think anyone could get that out of him. I believe that traumatized people, and I include myself —

How were you traumatized? The way I grew up.8 Traumatized people learn how to turn off what you’re calling a soul. It’s not that they don’t have one. It’s that the pain of emotion is so intense they turn it off. And I feel that Donald is caught up in getting the love of the masses, which is unobtainable and leads to no good.

How’s President Trump doing in your eyes? There’s a reason I didn’t vote for Donald. I believed in Hillary Clinton, because she was a career politician. She was into the job in the way her husband was. Bill Clinton, he didn’t want to take a vacation. Donald, I knew he would spend more time golfing than serving the White House. What can I say? I don’t get the focus of the administration, and I don’t get its divisiveness. I think Donald was a lot happier not being in the White House.

Have you tried to get him on the show since he became president? No. If he called me tomorrow and said, “I want to come on,” I would not refuse, but it would be contentious.

Is being caught up in trying to get the love of the masses something you can relate to? Absolutely. I can’t stand if somebody doesn’t like something I’ve done.

Which is quite a paradox for someone whose been as willfully controversial as you have. You’re right. I shouldn’t care about it, but criticism still affects me. In therapy we talk about the disconnect between understanding real love between two people and this idealization of the masses’ love. I bum out, because I want everyone to love what I’m doing.

Stern dressed as his Fartman character, with Jessica Hahn at the 1992 MTV Music Video Awards. Miranda Shen/Fotos International, via Getty Images

How much does being famous help your interviewing? I bet it lets you get away with things other interviewers can’t. It helps. To some extent people come in wanting to please me. And because I’m famous, and people know that I’m open — I talk about how small my penis is and every other thing in my life — that lends itself to an honest discussion. When I wrote the new book, I started to reflect on the art of interviewing. Because now with podcasts — I meet people and they go, “I have a radio show,” and I want to strangle them. I’m like, “No, you don’t. You’re doing a podcast.” People just talk and talk and there’s nothing exciting going on. To do a good interview, there’s a certain knowledge you must bring to it, a certain intelligence, a certain empathy. You have to not only do research but also have a sense of what keeps people interested, when to cut them off, when to help them out. It’s a whole process, and you have to labor over it. When I can look Jon Stewart in the eye and know the first punch line he ever said onstage,9 that sets up a vibe. There is an art to conversation, and we’ve lost that.

When you talk about podcasts — What I’m referring to is when you are put to the test in a broadcast situation, where you have to bring in subscribers or get ratings. That separates you out. There is no greater judge of whether you have talent or not than to go on a commercial radio station and try to attract an audience.

Do you listen to Joe Rogan’s podcast? I’m a fan of Joe Rogan. I’ve never watched the entire podcast, but there’s tons of clips of him, and he does a really good job.

Is there an issue between you guys? Yeah, there is. I was a fan of Joe’s comedy. He does a great routine about working out with weights with his buddy in the basement, and before you know it, they’re having full-on gay sex. So I was a big proponent of his before he was a host on TV, before he got into M.M.A. fighting or whatever. I used to have him on the show. Joe was a guest one time and I said something to him off the air, which I won’t go into, but he took offense. I haven’t heard or seen him since. I think he made the decision that I was toxic for him. But I hold no grudge.

Has he invited you on his show? He hasn’t. I’m not opposed to it. I’ve asked him to come on my show, but he doesn’t want to, and I respect that. It’s not meant to be.

Do you like people? I mean generally. That’s hard for me to answer.

Then the answer is probably no. The hard-ass answer is no. But I have this strange personality where I hide a lot from myself. Maybe I just can’t admit that I like people, and that’s what this book is about: starting to realize that maybe I do.

Just as long as you don’t have to smell them or touch them or look at them? Yeah, there’s some element of contamination in it all. I get home, and I want to be left alone. I crawl into a hole. I’m trying not to do that so much. I’m trying to remind myself that I’m a human being and need other people.

Stern at a book-signing event in 1995. Richard Drew/Associated Press

Are you ever worried about the prospect of people digging up old offensive material you’ve done? It’s not hard to imagine folks getting freshly upset. I am the poster boy for doing everything offensive. I’ve done insane things. But everything I did, I make no apologies for, because I was trying to entertain people. I wanted to be interesting and entertaining to that guy driving the car. But, you know, it’s painful for me to look back on my career, because a lot of that stuff I said I don’t know how much I believed.

I went back and reread “Miss America” and “Private Parts.” I hate both books.

The stuff in them about, for example, Rodney King10 or homosexuality11 makes it a little hard to countenance the idea that you were just trying to be funny. That’s my worst nightmare. I would take material from life: I was listening to someone talking about how homosexuality is a choice and I thought: This is wild, this is controversial, this is something I can say to shock. I don’t know that I ever believed that kind of thing. On the air I was just trying to grab at quarter-hours of people’s time to keep them listening. I mean, I grew up in a household where we were open about homosexuality. I am only a proponent of gay rights, gay marriage. I am so live-and-let-live about homosexuality. I try to preach tolerance to my audience. But if you read my books or listen to my old raps, I sound insane.

I think maybe you just got caught up in your answer, but you punted on the racial part of that question. Do you feel like you ever crossed lines about race? No, I never felt that way. I always felt that my commentary was valuable because of my unique upbringing. I grew up with the greatest hypocrisy a human being can ever see. I grew up in Roosevelt, Long Island.

Which you’ve explained was full of white liberals who talked about racial equality and then moved out when black families moved in. And that hypocrisy was my impetus. If I was going to be truthful on the air and talk about stuff that I knew, race would have to be included. Nothing was more startling in my young life than to see white people flee in the middle of the night, the same people who would tell me you have to love your black brothers. So in my life I’ve always had a discussion about race.

Were you ever aware of whether you were pandering when you talked about social issues? I wasn’t even aware. Listen, I believed that my career would end at any minute. The way that I felt that I could get mass audiences and ensure I’d get to work another day was to be the most outlandish, the most wild, the most funny and controversial, like a guy who had just gotten out of an insane asylum. And it wasn’t a contrivance. I thought I was letting out my id. I was unleashing parts of my brain that I probably should’ve kept quiet, but I felt it was a legitimate way to do radio. You might say, “What made you think that your id is so interesting?” It isn’t that my id is so interesting. It’s that someone was willing to do it. That was my approach, and let me tell you, some of that was damaging in my personal life. In my life now, I have a comfortable balance between doing a good radio show and being able to live with myself.

What’s a contemporary hypocrisy that bothers you the same way that liberal attitudes about race used to bother you? Mike Pence pissed me off when I was reading about his thing with Pete Buttigieg. This guy’s clearly antigay. Then, when he was asked about it, he said something like, “Everyone knows what is in my heart.”12 We know what’s in your heart! You don’t think a guy should have to bake a cake for someone who’s gay. I’m also pissed off about the amount of anti-Semitism in the world right now. I’ve seen a ton of that [expletive]. I’ve dealt with it my whole life. It makes me sick when these [expletives] are like all “Jews are rich, and they rule the world.” No one let me in on that! Anything can piss me off. I’m still an ornery bastard. Some guy says to me the other day: “What’s the big deal about Lori Loughlin buying her kid’s way into school? Any parent would do that for their kid.” I’m like: “What do you mean? I wouldn’t do that for my kid! That’s sending the wrong message.” You name it, I could get pissed off about it. I’m still pissed off everyone’s carrying on about this guy putting a ball in the hole, Tiger Woods.

What’s your problem with him? Because you hated him 10 minutes ago! Then he got the ball in the hole, and you’re redeeming him. Why did you hate him in the first place? You probably shouldn’t have hated him then, because what did his life have to do with you? And now that he was able to be No. 1 at putting the ball in the hole, you love him again. I don’t know. What doesn’t make me angry?

Stern with Paul Giamatti, in the 1997 movie “Private Parts,” based on his book of the same name. Paramount Pictures/Everett Collection

Does it bother you when an interview subject is performing what they think you want in an interview rather than just being in the moment? Look, there are some people who are so closed off they don’t want to go there. My biggest fault as an interviewer is I keep trying. If I don’t get to the [expletive] shot I go home and beat the [expletive] out of myself.

What’s an example? Robert Plant. I am such a fan of that guy, and I took the wrong approach. He came in, and I’m dying to ask him about Led Zeppelin. I wanted every detail. After a while he says something like, “I don’t want to talk about Led Zeppelin.” Then I go back and back and back because I was hyperfocused on thinking that’s what the audience wanted. So in some ways I blew it with him. But some people are just open books. Vincent Gallo.

He’s a lunatic. He’s a good interview!13

Who’s your dream interview? Mick Jagger. Oh, my God, I love the Stones. I sat in my room for years and listened to records because I didn’t have a lot of places to go. Musicians to me were like prophets. I learned more from musicians than I ever did from religious training. So to sit down with Mick Jagger and talk about his career — that might be incredible.

Speaking of religious training, is it right that one of your daughters is a rabbi? One of my daughters is a rabbi, but she’s in that phase where she’s still learning. I have another daughter who’s getting a doctorate in psychology. She’s been a social worker for years, dealing with the foster-care system. Then I have a daughter who’s a registered nurse and on her way to becoming a nurse practitioner. It blows my mind what my kids do. They’re way better than I am.

Did you raise your kids with religion? If you didn’t, it must be interesting to have a child embrace Judaism so strongly. As far as raising the kids, I would not have really given them any religion. My ex-wife14 believed that they should have it, and my kids ended up loving it. They got comfort from it. Being Jewish for me was always wonderful. Well, it was a double-edged sword. I had experienced a lot of anti-Semitism. But I liked being with other Jews, and I’d go to Jewish summer camp. I never was superreligious, but I understood the importance of Israel and of Jews needing a homeland because of persecution. So I’m very pro-Israel on the air.

You get into this in the book, but when you took a sick day from work a couple years ago, you conspicuously decided not to talk about the specifics on the air. Seems weird, right?

Yeah, only because in the past you seemed happy to discuss your anal fissures, among other things. I know.

Stern debuting his show on Sirius Satellite Radio in January 2006 at the network’s studios in New York City. Getty Images

Can I tell you my theory? My guess is that because the sick day had to do with a cancer scare, that meant it also had to do with mortality. And that was something you couldn’t bring yourself to talk about. One hundred percent. Talking about it would have been like admitting to the audience that I’m getting old. I’ve never really believed I was going to die.

Few people do. No, and I can’t come to grips with it. This was my first major health sock-in-the-head.15 I couldn’t bear telling the audience that I was human. I just wanted to recover. I have the strongest work ethic of anyone I know, and yet I was so heavily criticized for missing one day. But you’re right. I could not bring myself to admit my own mortality.

Can you now? I’m struggling.

Does that play into any thinking about retirement? I don’t know myself that well. I can say to you with almost 100 percent certainty that I would retire at the end of this contract,16 but I say that about the end of every contract. I’m afraid to walk away.

Why? A lot of my life force is generated from that radio show. When something’s bothering me, I can go on the air and work it out. Or if I’m lying in bed and think of something funny, I can go on the air and unleash it. That rush is remarkable. But I have two more years on this contract. I don’t know how I’m going to feel physically when it ends.

That reminds me: Did you say on the air the other day that you only listen to music that bums you out? Yeah, I’m only moved by sad music. What was that song where they mixed in B.B. King’s singing? “I’ve been downhearted babe/Ever since the day we met.”

Primitive Radio Gods.17 Oh, you’re good. That song gets me. I hear that, and I start crying. “My Hero” by the Foo Fighters wrecks me. If a song sounds happy, I don’t want to hear it.

So these day-to-day things that cause you anxiety: public approval, your schmekel. Schmekel, huh?18 No one uses that anymore.

I’ll annotate it. But things like that and the fact that you’re now 65 years old and aware of death — on this day, how are you handling all that? I’m going to give you a fair assessment: I don’t know. In some ways I’ve made inroads into living a mentally healthier life. I still have a long way to go. I’m running out of time, though. All that neurosis and all that fixation on getting an audience sucks your energy out. I went through a divorce, and I don’t want that again. Beth19 means everything to me. My kids mean everything to me. I will tell you I feel less pressure now — not because of my age but because of therapy. I’ve realized I don’t have to hit you with a sledgehammer. It can just be a hammer.