Transcript for Radio legend Howard Stern recalls interviewing Trump
But now we're going to turn to George's interview with Howard Stern. We hear it's very candid. It is candid. He has no filter but this book is still full of surprises, a lot of self-reflection from Howard as well. Takes us inside how he's changed over the years and the art of interviewing. He also opens up about his most famous guest president trump and Hillary Clinton, the one that got away. Coming to the Howard Stern show. Let me take five minutes. Reporter: When you interview Howard Stern -- I'm in charge. This is my interview. Reporter: -- The mic is always hot but now he has a new book. "Howard Stern comes again." He's trying to answer questions about his most memorable moments on air. We have to talk about Donald Trump. He is a big character in the book because -- Big character on my show. That's what I was going to you say one of your best guests Donald Trump hands down whenever you put him on the air, now this, is before he was running for president, he was an open book. He would say anything. And, you know, oddly enough during the campaign and even now people quote these interviews that I did. Big time. Big time. I was quite surprised when they dragged out every single Donald Trump interview I had done and in some ways I felt it was unfair to trump because, like, for example, they were fond of quoting that Donald Trump had something -- 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. Having said that, though, 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 -- ah, she's a 6, you know. Now, who says that? You know? Most people if they're having that thought keep that pretty guarded. Not Donald. He was right into it. Ivanka Trump. You know who is one of the most beautiful girls -- Who? Ivanka. I would marry her. Did you feel in some way you helped make him president. Absolutely. Because Donald would come on my show. I mean, look -- Does it make you feel bad or good? Well, look, I did not vote for Donald Trump. I go into great lengths in this book and I think people will be interested in this. Hillary Clinton, you know, like in "Moby dick" I was chasing her. She was my obsession. I wanted to see Hillary Clinton win and I thought if she had come on the show, the way I helped Donald was I let him come on and be a personality. Whether you liked him or not, people related to him as a human being. I wanted to do that for Hillary. The big knock against Hillary, especially with some of the male audience was, eh, we don't like her. You could feel that on the air. I absolutely could feel it on the air. All during that time you do write about this, you're trying to get Hillary Clinton on your show as you said, she's afraid of you. Hillary Clinton is afraid of me and justifiably, look, she's got a big campaign. She doesn't know about I'm in therapy and doesn't know that what I really wanted to do -- I didn't want to ask her about her sex life or Bill Clinton and his affairs. The woman has devoted her life to public service. Why? What is it about public service? What is it that drives her? What was it like when she saw her -- when her husband became president. 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. You believe if she had done that she'd be president? That's an arrogant statement and, you know, to sit here and cavalierly say, yeah, she would have been president. No, but look at the electoral college and look at that. It came down to a couple of states and it was -- 70,000 votes. 70,000 votes. On Sirius XM we have 33 million subscribers and we calculate that at a minimum per subscription there are two people listening per family. Let's say there's 66 million people, they tell me 60% of Sirius' audience listening to me. Out of that audience if Hillary had come on in the same way that lady gaga came on or Gwyneth paltrow or Rosie o'donnell and guys call me afterward, man, I never liked lady gaga. But I just heard her talking, I'm going to her concert. These are hard-core dudes who don't get sometimes -- they're too caught up in she is a woman or I look like a wuss if I'm listening to this. If Hillary could have come in and maybe persuaded 70,000 people out of those millions of people that listened and come off in such a way, main we'd be looking at a different scenario. Reporter: Now stern and trump not as close as they used to be. The turning point in my relationship with Donald was he did ask me to speak at the convention. And I had to say no. And -- Were you tempted at all? Well, since I was a Hillary supporter, for a minute I thought I'll go up and endorse Hillary, which would have been a great moment. You wish you would have done that now? No, I wouldn't do that to Donald. You know, it's a weird relationship. Donald was at my wedding. I remember having very warm feelings for Donald and I do. He was always very nice to me. I've had dinner at mar-a-lago many times. That's why I couldn't believe Donald wanted this all to work out for him because if you go to mar-a-lago, it's like a piece of heaven. It's a beautiful place. And I'd go there to eat dinner with my wife. And by the way I was never comped. I paid. So we weren't that good of friends and I remember thinking why would a guy want to leave this? I he plays golf every day. You don't want him to be president but you can't help like him? Well, I have a real problem as you can tell, if I was a Hillary Clinton supporter you can tell 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'd probably get a few people abortions. I don't know what he's doing. The stance, the women don't have a right to choose what -- you don't have to get an abortion. But if you want the right -- I remember the days of women in the back alleys with coat hangers, that's not acceptable and you know who used to be able to get abortion, rich people. They could get them. And so, you know, let's face it, it is really unthinkable to me about what's going on in the country right now. Howard doesn't like to think about his previous books either. The new one inspired by a health scare he kept secret from his listeners. I had been diagnosed with kidney cancer and I had to go in for surgery and I was freaking out. I go, this can't be and they had told me it was 95% chance it was cancer. It turned out not to be cancer. It was a miracle. When it passes did you have that Winston Churchill feeling of nothing being more exhilarated than being shot at and missed. Well, that's why I think I also wrote this book. All of a sudden it brought me to some kind of reality, you're not going to live forever and what am I most proud of? What do I want my children to see. What do I -- and these interviews and what I've written here represents to me the best of me. The best but he does not shy away from the worst of himself either. Like I said he talked about his past books and said he can't even look at them anymore and he also opens up about what he considered his worst interview ever and that is revealing as well. We'll talk about that in our next hour. You also have an extended version on "Nightline." And hulu will play basically the whole interview. Oh, wow. He doesn't hold back. We see that.
This transcript has been automatically generated and may not be 100% accurate.