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. a collection of his most private interviews. >> do you feel in some way you helped make him president? plus turn around. the interview that howard stern calls his worst to date. >> it was insulting it to to but all i cared about was being the man. plus, the life-changing health scare. >> i was freaking out.

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

good evening. evli hisu pofor joining us. best and worst interviews,

including donald trump before his presidency. here's stephanopoulos. >> howard stern comes ago. tell me where the title comes from. >> i wanted to inform the audience that i haven't changed, that i still have second grade humor. and hearing guys like you, respected broadcast journalists saying howard stern comes again. i'm coming again. >> reporter: howard stern calls himself the king of all media, his speciality, no-holds-barred interviews. >> do you have in think? >> i'm sure i don't. >> i saw you as a victim.

>> reporter: now out with a new book reflecting on some of his biggest guests. >> donald trump would come on my show, and this was why he was great. there was no filter, i'd go, donald, angelina jolie, she's one of the most beautiful actresses in the world. ah, she's a six, you know. 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 in the world? and i helped create her? >> who. >> ivanka. >> most beautiful girl in the world. i would marry her. these types of things most people, certainly, politicians don't say. >> reporter: some of the dozens of interviews stern did with trump resurfaced during the 2016 election and he didn't see the impact. >> i was surprised when they drug out every interview i'd done.

in some ways i thought it was unfair to trump. they were fond of quoting donald trump said something to the effect that stds were his personal vietnam, but it really 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 that in some way you helped make him president? >> absolutely, because donald would come on my show, look -- >> reporter: does it make you feel bad or good? >> well, look, i did not vote for donald trump. the way i helped donald was i let him personality. i don't think he thought he was going to win. and i don't think he expected to win. i think was a publicity stunt.

what i mean by that is, 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. he never announced he was running. 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 will to say no. >> reporter: 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. >> reporter: you wish you would have done that now? >> no, i wouldn't do that to donald. you know, it's a weird relationship i have. donald was at my wedding. he was always 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. 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. it is really unthinkable to me about what's going on notice 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? 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 would be president? >> that's an arrogant statement. it came down to a couple states, 70,000 votes. on sirius xm we have 33 million subscribers. if hillary could have come in and persuaded 70,000 people out of those millions of people who listenen and come off in such a way, we would be maybe looking at a different scenario. >> reporter: his 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 one to contract herpes. >> reporter: he doesn't want to be just a shock jock. he writes about some of his

regrets, saying he was self-absorbed and had a hard-ass pose that no longer works. he doesn't want people to read his other books, including the 1993 best seller "private parts." >> you're getting a look at the live broadcast of the howard stern show. >> it just 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 bam, let all out. that was my approach to radio. >> reporter: was that a conscious approach then? or was it just you? >> no, no, it was a conscious approach. that's whatly i had to do. but 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 like that guy. >> i'm not in love with that guy. i never was in love with myself. that comes across in the book. i have problems, but i have learned through therapy, maybe i could love myself a bit and love what i'm doing and really throw myself into it, it's been a long process and long journey. >> reporter: it began with a split from his first wife alison. >> i was scared out of my mind. i'd been married most of my life. my daughters are the most important thing in the world to me. how do i as a man have a relationship with my daughters outside of if my wife is no longer there to facilitate that, how do i communicate that? how do i have a successful relationship with any woman or man for that matter if i don't even know, if i don't know what's up and what's down. and when i got into therapy,ly

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 story. i'm primarily being funny and provocative for my audience. but i never really been in, alone in a room 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, impressions of my mother, impressions of my father. >> reporter: you're going to be the best patient. >> the best patient, because i want to be loved, and he turned to me and says none of this is funny, and i said i do this for a living. he said some of what you're telling me sounds very sad but you're laughing at it. this was mind-blowing to me. no one had ever said that to me,

and i never had a conversation like that. 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. >> thank you, george takei. >> reporter: the move from traditional radio to subscription-based radio gave him room to grow. >> the format of sirius xm radio 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 outrageousness, all the sex talk was liberating and revolutionary to me because i was on terrestrial radio. i was fighting the good fight. now i get on satellite radio, and suddenly, my world is like, do whatever you want. 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 helped him get over himself. >> not having to worry about the size of the audience, when i'm sitting there, i said what would it be like to really hear what someone has it 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 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 in the book is 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 think he got to show that full range. >> up next, a health scare changing his life and the interview he regrets the most. [ sniffing ] come on. this summer, add a new member to the family. hurry into the mercedes-benz summer event today for exceptional offers. lease the glc 300 suv for just $419 a month at the mercedes-benz summer event. going on now.

with advil liqui-gels, what stiff joints? what bad back? advil is... relief that's fast. strength that lasts. you'll ask... what pain? with advil liqui-gels. want to brain better? say hello to neuriva, a new brain supplement with clinically proven ingredients that fuel five indicators of brain performance: focus, accuracy, memory, learning, and concentration. neuriva. but their nutritional needs remain instinctual. that's why there's purina one true instinct. high protein for strong muscles. a different breed of natural nutrition. purina one true instinct. also in grain-free for dogs and cats. but one blows them allmany moisturizers... out of the water. hydro boost with hyaluronic acid to plump skin cells so it bounces back... neutrogena® and try our hydrating makeup.

depend® fit-flex underwear for all day fun... features maximum absorbency, ultra soft fabric and new beautiful designs for your best comfort and protection guaranteed. life's better when you're in it. be there with depend®. did you know you can save money by using dish soap to clean grease on more than dishes? try dawn ultra. dawn is for more than just dishes. with 3x more grease cleaning power per drop, it tackles tough grease on a variety of surfaces. try dawn ultra.

♪ ♪ this is how driving should feel. the tech-advanced nissan leaf. the best selling electric vehicle of all time. this is nissan intelligent mobility. ♪

shshow me homecoming. babwe also live with youtube. okat&t's internet "security." do you know the mother's maiden name? at&t! there's an army of weirdos outside. they're just trying to get on your network. why didn't you alert us? alerts aren't really my thing. what is your thing? ok, i am sensing a little hostility from you, janet. so i'm going to be the grown-up here and excuse myself. stop living with at&t. switch to xfinity for real-time security alerts for all your connected devices.

howard stern says he's now in pursuit of the best version of himself, a health scare motivating him it to write and reflect. here's george stephanopoulos. >> we're such an odd this is difficult for me. >> reporter: when you interview howard stern, the mic is always hot. >> this might be a shock, george and i are actually friends. we get together with our wives for dinner at our house. and 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 ali, george's wife will say, and george is an intellectual. weren't you some sort of rhoads scholar or something? weren't you almost a priest or something? >> reporter: coming to the howard stern show.

>> inevitably, ali will go, george and i have sex every night. i'm like. and george sits, 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? now i'm going to tell you something. my wife, i love her. she's a wonderful woman, beautiful woman. we have sex, you know, normal couples, george. i didn't know, and you, i never think of you as a sex i said can you picture george and ali every night? >> reporter: completely hijacked right here. >> but george, that can't be true. >> reporter: it's not true. it's not true, but we do well. we're doing fine. >> i feel bad, something's wrong my marriage. >> reporter: today stern is happily married to his second

wife, beth. with the help of therapy, he says he's doing the best work of his career. and part of stern's evolution comes from acknowledging his mistakes, including his 1986 interview with robin williams. >> i 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 pressure that i couldn't be gracious enough to allow robin williams, imagine the air kbans rrogance of me. >> reporter: you write about that. it's a heartbreaking story. you tried to reach him and apologize. >> when i finally realized that hey, it's okay it to be a fan of someone. i've been such a hard-ass on the air. i have such a desire to have all of 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. it 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: so when it passes, did you have that old winston churchill feeling of nothing being like being shot at and missed? >> it brought me to a reality, you're not going to live forever. what am i most proud of? what do i want my children to see? and these interviews and what i've written here represents to me the best of me. >> howard stern's new book is available in stores now. a final thought when we come back. trampoline. ahh brain freeze! no, it's my teeth. your teeth hurt? sensitivity. i should do something about it. 80% of sensitivity starts at the gum line, so treat sensitivity at the source. new crest gum and sensitivity starts treating sensitivity immediately, at the gum line, for relief within days and wraps your teeth in sensitivity protection. ohh your teeth? no, it's brain freeze! crest. healthy, beautiful smiles for life.

depend® fit-flex underwear for all day fun... features maximum absorbency, ultra soft fabric and new beautiful designs for your best comfort and protection guaranteed. life's better when you're in it. be there with depend®. want to brain better? say hello to neuriva, a new brain supplement with clinically proven ingredients that fuel five indicators of brain performance: focus, accuracy, memory, learning, and concentration. neuriva. before discovering nexium 24hr to treat her frequent heartburn, marie could only imagine enjoying freshly squeezed orange juice. now no fruit is forbidden. nexium 24hr stops acid before it starts for all-day, all-night protection. can you imagine 24 hours without heartburn? for all-day, all-night protection.

♪ want to freshen your home without using heavy, overwhelming scents? introducing febreze one. it eliminates odors with no heavy perfumes, so you can feel good about using it in your home. for a light, natural-smelling freshness, try new febreze one. when crabe stronger...strong, with new nicorette coated ice mint. layered with flavor... it's the first and only coated nicotine lozenge. for an amazing taste... ...that outlasts your craving. new nicorette ice mint.

...you discover paint bleed you under your tape...... not with frogtape! frogtape is the only painter's tape treated with patented paintblock technology. paintblock reacts with the water in latex paint to form a micro-barrier against paint bleed, giving you the sharpest lines possible.

get professional results with frogtape... no messy lines, no paint bleed. for sharp lines every time, frog it! has been excellent. they really appreciate the military family and it really shows. with all that usaa offers why go with anybody else? we know their rates are good, we know that they're always going to take care of us. it was an instant savings and i should have changed a long time ago. it was funny because when we would call another insurance company, hey would say "oh we can't beat usaa" we're the webber family. we're the tenney's we're the hayles, and we're usaa members for life. ♪ get your usaa auto insurance quote today. it'it's crepe dayday for a family traditiony's. ♪ we started about 22 minutes ago and now we can continue that tradition at home with free denny's delivery. see you at dennys.com

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 can catch the full howard stern interview and all of our episodes on hulu. that's "nightline." thanks for the company, america. goodnight.

after qualifying purchases when you apply and are approved for the hawaiian airlines world elite mastercard. plus, you earn miles on everyday purchases. get closer to the travels and moments you'll remember forever with this special offer. need another reason? enjoy an introductory no annual fee. to apply, visit hawaiianairlines.com