Howard Stern on what he learned in therapy, abandoning 'pure id' persona: Part 1

The legendary radio host opened up to ABC News' George Stephanopoulos about making big life changes and the best interview he's ever done.
11:22 | 05/15/19

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Transcript for Howard Stern on what he learned in therapy, abandoning 'pure id' persona: Part 1
Howard Stern comes again. Say that again. Think about it. Howard Stern comes again. I love that. Tell me where the title came from. I wanted to sort of inform the audience that I haven't changed. That I still have second grade humor. And hearing guys like you, respected broadcast journalists say Howard Stern comes again. Oh, my god, I'm coming again. Howard Stern calls himself the king of all media. His specialty, no holds bars interviews. Would you be upset if they replaced you as toney stark in ironman? Are you easy to life with? Even president trump. During the Ivana divorce case, I saw you as a victim. I like it. Do you know why? Reporter: Now with a new book reflecting on some of his biggest guests. Donald Trump would come on my show, and this is why he was great. There was no filter. I'd go Donald, Angelina Jolie, one of the most beautiful actresses in the world. Ah, she's a six. Now who says that? Most people, if they're having that thought keep that pretty guarded. Not Donald. He was right into it. You know who's one of the great beauties of the world according to everybody and I helped create her? Who? Ivanka. The most beautiful girl in the world. I would marry her. These types of things most people, certainly politicians don't say. That would have been embarrassing. Reporter: Some of the dozens of interview he did with trump resurfaced during the 2016 election and stern says he didn't foresee the impact. I was quite surprised when they dragged out every single Donald Trump interview I had and in some ways I thought it was unfair to trump. They were fond of quoting that Donald Trump said something to the effect that STDs were his personal Vietnam. But really, it was in a very joking scenario. He was not comparing his life to a Vietnam vet. It was ha, ha, ha, and this and that. But when journalists took it and made it serious, I thought it was a little unfair. Reporter: Do you feel in some way you helped make him president? Absolutely. Because Donald would come on my show, I mean, look -- Reporter: Does it make you feel bad or good? Look, I did not vote for Donald Trump. The way I helped Donald was I let him come on and be a pirgeity. He's a master at talking like a dude. Reporter: Stern didn't take candidate trump seriously at first. I don't think he expected to win. I think it was a publicity stunt. When he put out his first book "Art of the deal", they said why don't you announce you're running for president and it will help sell books and get you on every show. He never announced he was running, was going to run. What happened this time was the apprentice ratings were going down, NBC was balking at giving him a big contract. And lo and behold, I'm running for president. Reporter: Once trump became president their personal and professional relationship changed. The turning point in my relationship with Donald was he did ask me to speak at the convention, and I had to say no. Reporter: Were you tempted at Well, since I was a Hillary supporter, for a minute, I thought, well, I'll go up and endorse Hillary. Which would have been a great moment. Reporter: You wish you would have done that now? No, I wouldn't do that to Donald. It's a weird relationship. Donald was at my wedding. He was always very, very nice to me. Reporter: You don't want him to be president but you can't help but like him? I have a real problem with what's going on. So I'm very conflicted now. The guy I knew doesn't, I didn't know this was him. I don't believe his stance on abortion for example. The Donald I know, I think he probably needed to get a few people abortions. I don't know what he's doing. It is really unthinkable to me about what's going on in the country right now. Reporter: Stern describes how during the 2016 campaign he was running his own campaign, to get Hillary Clinton as a guest. She doesn't know about I'm in therapy and what I really wanted to do. I didn't want to ask her about her sex life or Bill Clinton and his affairs or any of that. The woman has devoted her life to public service. Why, what is it about public service? What is it that drives her? What was her climb? I thought that perhaps if she came on my show we could have stripped away some of the pomp and circumstance or the tightness that comes with running for president and like Donald, she could have been seen in a different light. Reporter: And you believe if she had done that she'd be president? That's an arrogant statement. It came down to a couple of states. 70,000 votes. On Sirius XM we have 33 million subscribers. If Hillary could have come in and maybe persuaded 70,000 people out of those millions of people that listen and come off in such a way, maybe we'd be looking at a different scenario. Reporter: Stern's platform is powerful. Respect my total domination of the media. Basically, humble yourselves before me. Reporter: And he built it through controversy. We can laugh, we can play. We can do whatever the F we want. Reporter: And at times indecency. I'll be the first to contract herpes. That interests me zero. Reporter: In his book he writes about regrets, saying he was self-absorbed. He doesn't want people to read his other books, including the 1993 best-seller turned blockbuster "Private parts." You're getting a look at the Howard Stern show. And you're licking whipped cream. It doesn't represent me anymore. It's hard for me to go back and look at it. Those books could be hurtful. And they were a little too intense. At that point, my attitude was it was a scorched-earth policy. I'm going to blow you out of the water. I'm going to be pure id. And bam, let it all out. That was my approach to radio. Reporter: Was that a conscious approach then? Or was it just you? No, it was a conscious approach. That's what I had to do. But it was me. When you're on the radio and trying to attract an audience, everything is intense. Everything is super blown up. Reporter: When you read this book, it doesn't sound like you love that guy that much. I'm not in love with that guy that much. I never was in love with myself. And I think that comes across in the book. I have problems. But I, I have learned through therapy, maybe I could love myself a bit and love what I'm doing and really throw myself into it. And it's been a long process and a long journey. Reporter: It began with a split from his first wife Alison in 1999. A wakeup call that led to therapy. I was scared out of my mind. I was married most of my life. My daughters are the most important thing in my life to me. How do I have a relationship with my daughters if my wife is no longer there to facilitate that. How am I going to have a successful relationship with any woman or man for that matter if I don't know what's up and what's down? And when I got into therapy, I had to start learning how to be a man. I didn't have any lessons. Reporter: Being listened to in therapy helped him listen more on air. Yes, millions of people were listening to me on the radio. But I was telling stories. I'm primarily being funny and provocative for my audience. But I never really had been in a room alone with a man where he heard me and listened to me. The first session I went in, I'm sitting there, and I'm doing some of the best radio routines I've ever done, I'm doing impressions of my mother, of my father. Reporter: You're going to be the best patient. The best patient, because I got to be loved. And he turned to me, and he goes none of this is funny, and I was like hey, I did this for a living. He goes, why don't you get real with me. Some of what you're telling me sounds very sad but you're laughing at it. This was mind blowing to me. Nobody had ever said that to me, and I'd never had a real conversation like that before. And as the years went by, I got more and more turned on by being listened to. Quite frankly, I was very uncomfortable with it. And now the Howard Stern show. Thank you, George Takei. Reporter: The move from radio to subscription-based satellite radio gave him room to grow. The format of Sirius XM has allowed me to be a lot freer. Everyone said oh, you're going to Sirius XM so you can be as dirty as you want to be. All the outlayousness, all the sex talk was liberating and revolutionary because I was on radio, the government was being oppressive. I was fighting the good fight. Now I get on satellite radio, and suddenly, my world is like, oh, do whatever you want. It's the wild west. And so suddenly, who am I railing against? Who am I fighting? Who is the enemy here, you know? And it turned out I had to rethink the whole thing. Reporter: Being free from the pressure of ratings helps stern get over himself. Having four hours to do whatever I wanted and not having to worry about the side of the audience, when I'm sitting there. I said what would it be like to really hear what someone has to say? And it has led to some incredible conversations. When I let go of it. So it takes that pressure away. I can do what I really want to do. And what I wanted to do is listen to people and ask them all of the questions that I had. Do you suffer from depression? Are you medicated? I'm medicated. I used to think I needed to be incredibly unhappy to be funny. When I was interviewing conan, because I was able to listen and not trying to insert myself, I picked up on something he said, and then all of a sudden he started talking about that he suffered from depression. We got into this heavy thing, and it was, it was, it was like the cameras disappeared. The microphones disappeared. And the two of us were just locked in conversation. Reporter: Best interview you ever did? Best interview I ever did. The reason I chose him as the best one in the book is that I felt satisfied. He is so smart and so funny that I think the format he's locked into with late night television, he doesn't get to show the full range of who he is. And in this interview, I felt I got to show that full range.

This transcript has been automatically generated and may not be 100% accurate.

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