this is "nightline." tonight, one on one. the radio legend laying it bare. >> i never was in love with myself. >> howard stern opening up to george stephanopoulos about how he's changed his ways. regrets about past behavior. his new book a collection of his most memorable interviews, including then private citizen donald tru se wayyou helped mak? plus turn around. the interview with actor robin williams that howard stern calls his worst to date. >> it was insulting to him. but all i cared about was being the man. >> the mistakes he made and apology that came too late. plus the life-changing health scare. >> i was freaking out.

this can't be. but first, the "nightline" five.

good evening. thank you for joining us. tonight, the no-limits interview with radio host howard stern, reflecting on the highs and lows of his career and revealing his best and worst interviews,

including donald trump before his presidency. here's abc's george stephanopoulos. >> 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 interviews 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 done. 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. wheth he's a master at talking like a dude. >> reporter: stiern 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 all? >> 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? what's goi on.al problem with

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 h herpes. >> that interests me zero. >> reporter: in his book he writes about regrets,self-abs. e

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, everyt super blown up. >> reporter: when you read this.

>> 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 pmy life to me. how do i have a reaplationship 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 foreth that matter 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 subscptn-sed limo glw.>> the to 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. >> up next, a health scare changing stern's life. in the interview he regrets the most.

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howard stern says he's now in pursuit of the best version of himself. mistakes and a health scare mote skr vating him to write and reflect. here's george stephanopoulos. >> we're such an odd couple. show the book and -- this is difficult for me. >> reporter: when you interview howard stern, the mic is always hot. >> this might be a shock to people. george and i are actually friends. we get together for dinner with our wives quite often at my house. and by the way, full disclosure. george is one of the best dinner guests. but you cause a little bit of a rift. and i'll tell you why. we're sitting at dinner, and alley, george's wife will say, george is an intellectual. weren't you some sort of rhoads scholar or something? weren't you a priest or something? >> this is coming to the howard stern show. >> let me take five minutes for

this. but yiinevitably, ali will go, george and i have sex every night. i'm like, and george doesn't laugh. he sits there like this. you never let on. i don't know what's going on. and then after you leave, you and ali leave, i go, did you hear that? my wife, i love her. she's a wonderful woman, a beautiful woman. we have sex, you know, you know, normal couples, george. you know, i didn't know, and you, i never think of you as a sex finend. and i said, can you picture george and ali every night? >> reporter: completely hijacked right here. >> that can't be true. >> reporter: it is not true. we do well though, we're doing fine. >> i feel bad. i go something's wrong with my marriage. >> reporter: today stern is happily married to his second

wife. with the help of thisserp thera he's doing the best work of his career. >> i believe blew him right out of the water, why? i'm thinking i'm the most important thing here. robin williams goes on about something. my audience will tune out. i have to keep their interest. it was such a tha i couldn't be gracious enough to allow robin williams. imagine the arrogance of me, thinking robin williams can't hold my audience. >> reporter: you write about that. you tried to reach him and apologize. >> yeah. when i finally realized that a, it's okay to be a fan of someone, you know, i've been such a hard-ass on the air. i had such a desire to have all the audience for me. that i couldn't be gracious. there's no room for anybody else. so i couldn't be a fan of anyone else. and here i am a huge fan of robin williams. i've seen everything he does.

his stand-up is mind-blowing, and he comes into my studio, and what do i do? i go hey, i read you're having sex with your nanny, you left your wife for your nanny or something like that. now that's clobbering somebody over the head. that doesn't lead to discussion. it was insulting to him. but all i cared about was being the man. >> reporter: so when you walked off the air that day, you said, i nailed it? got it? >> yeah, yeah. i was clueless. >> reporter: in his book, stern writes that it took him 20 years to work up the nerve to apologize, but williams died before he got the chance. and facing his own mortality is one of the reasons stern wrote this book. >> i had been diagnosed with kidney cancer. and i had to go in for surgery, and i was freakin' out. i go, this can't be. and they had told me, it was 95% chance it was cancer, and it turned out not to be cancer, it

was like a miracle for me. >> reporter: when it passes, do you have that winston churchill feeling of being shot at and missed? >> yeah, i think that's wehy i wrote this book. it brought me to the reality, you're no you're not going to live forever. these interviews represent to me the best of me. >> howard stern's new book is available in stores now. a final thought when we come back. ♪ tired of constantly battling lingering smells in your home, like pet, shoe, and body odors? for long-lasting, continuous freshness, try febreze plug. febreze plug provides 1200 hours of freshness, with a unique dual chamber design that alternates between harmonized scents for a continuous renewal of fragrance. plus, febreze plug is formulated with odorclear technology, which cleans away odors instead of just masking them. for freshness you'll notice week after week,ug.

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finally tonight, it was a wise soul who told me once, quote, there are only two kinds of people. those who are humble and those who will be humbled. you c catch the full howard stern interview and all our episodes on hulu. that's "nightline." thanks for the company, america. goodnight.

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