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Talking into a microphone for most of his life with no sign of shutting up, Howard Stern responded to a challenge by a publisher to share the interviews over the years that seemed most revealing to him.

To some of those subjects, Stern now admits he owes an apology for his unrelenting compulsion to ask antagonizing and over the top crude questions – but always shocking. 

In this new book, Howard Stern Comes Again, published by Simon & Schuster, he confesses that his biggest regret is that he never got to apologize to Robin Williams after his interview in the early nineties.

'When Robin came on the show, I spent the entire time badgering him about how he had divorced his first wife and remarried his son's former nanny. I was attacking the guy, and he was justifiably furious with me', Stern writes.

Stern only realized years later that he needed to apologize – after years of psychotherapy to understand his own narcissism that had prevented him from even considering what someone else might be feeling.

Twenty years after the interview, he got up the nerve but it was too late. Robin died before Stern could make that call.

'I'm still filled with sadness over his loss and remorse for my failure to reach out sooner', the shock jock admits.

But Stern decided to take on the challenge of pulling together interviews over the years where he was able to draw out shocking confessions – even if it was said to keep the ratings up.

Howard Stern reflects on his controversial 30-year career in his new memoir Howard Stern Comes Again and details his most shocking interviews 

Madonna  

Madonna confessed in 2015 that she was 'extremely neurotic' and it was ingrained in her that she had to work having grown up poor, even after selling 300 million albums.

She dated Tupac Shakur and 'he got me all riled up about life in general'.

She was once in love with Warren Beatty.

She doesn't have many celeb friends but could relate to Michael Jackson, a painfully shy person.

'I think he felt eternally tortured by people. I think Michael was never happy with the way he looked. It was hard to him to look into people's eyes.

Pop star Madonna told Stern in 2015 that Tupac Shakur 'got her all riled up' and she was once in love with Warren Beatty 

Jenny McCarthy

'I'm very sexual. I love sex. I masturbated on top of my teddy bear. He did all the dirty work, so to speak, until my mom sold it in a garage sale, which was really hard on me,' the actress confessed to Stern.

'I would just sit on it,' she said.

'I was in the eighth grade.

'Some guy bought the teddy bear for his kid, which is beyond embarrassing'.

McCarthy continued to describe her favorite sex positions - in detail. 

Actress Jenny McCarthy has appeared on Stern's show multiple times - once with husband Donny Wahlberg - and explained how much she loves sex 

Tracy Morgan

Recovering in the hospital after a near fatal accident with a Walmart truck in 2014, the stand-up comedian confessed that his brain had shut down and he didn't feel any pain when the accident occurred and he went into a coma.

He also didn't feel any pain when he masturbated in the hospital.

'All I do is masturbate', he told Stern.

'I beat my d**k like it owed me money. My d**k got a restraining order out on my hand.

'I woke up one morning and my d*ck was dialing 911'.

'My heart machine was going off one day and they started running to my room and they opened the door. There I was beating my d*ck'.

'You were going to beat off the pain', Stern commented. 'I'd blow you if your d*ck wasn't so big'.

Comedian Tracy Morgan said 'all I do is masturbate', even after his near-fatal 2014 car accident 

Kim and Khloe Kardashian

The Kardashian sisters came on Stern's show in 2009 and he admitted, 'I didn't understand their talent. I didn't even know if they had one.'

So he asked Khloe about dating black men.

'Once you go black, you just never go back,' she said, admitting to only have dated black men.

But Kim said Khloe's rule isn't' always true. 'She's only black guys, I'm not'.

'Maybe it's because we have such big a**es, like the black guys like,' Kim said.

Both admitted to liking to be spanked, getting their hair pulled and talking dirty in bed.

Khloe Kardashian has appeared on Stern's show, once with her sister Kim, where she confessed she only dates black men 

Late night talk show host Stephen Colbert shared a tragic experience of losing his father and two brothers in a plane crash when he was 10 

Stephen Colbert

The late night talk show host confessed that he lost his father and two of his brothers in a tragic plane crash when he was only ten years old. 

It was a shattering experience for the young boy.

He did not listen to the cockpit recorder but he read the transcript.

'It happened by accident, actually. I wasn't looking for it. I was doing a little research on the accident itself. 

'I had found out from somebody else that the Sterile Cockpit Rule had been instituted because of that crash. So I looked it up and the first thing that came up on the Google search was the transcript. I went, ''I can't not read it now.'' So I read it. Yeah. It doesn't end well'.

Jerry Seinfeld

After the interview with Stern in 2013, the comedian said he'd never come on the show again. It was perfect.

And he turned down more than $100million to do one more season of Seinfeld because he felt the show had reached perfection.

'I'm never not working on material.

'Every second of my existence, I'm thinking, ''Could I do something with that?'''

Even when he's with his wife who he adores, 'I'm not authentically with her. I'm looking for a joke'.

Jerry Seinfeld told Stern on his show that he's always thinking of jokes, even while with his wife, saying: 'I'm not authentically with her. I'm looking for a joke'

Andy Cohen

The radio and talk show host and producer wanted to lose his virginity with a straight couple, he revealed. 

So he hooked up with a heterosexual couple in Boston while on a book tour – after the man sent him 'an incredible d**k pic'.

He shared it with Kelly Ripa and then met with them.

The couple madly f**ked, Andy never joined in but then the guys jerked each other off.

Radio and talk show host Andy Cohen wanted to lose his virginity with a straight couple, he revealed to Stern

Before he was known as the disgraced Hollywood producer, Harvey Weinstein told Stern he never took advantage of his powerful position 

Harvey Weinstein

The disgraced sexually abusive mogul told Stern he never took advantage of his position.

'It doesn't work that way. The movies are too expensive. The risks are too great'.

'You don't dream about strange p*ssy', Stern asked.

'I dream about Lord of the Rings', Weinstein answered.

Rosie O'Donnell

The comedienne became a close friend of Stern's after he went through therapy and realized he didn't have to knock her down.

She encouraged him to pursue painting and escape his self-imposed quarantine.

Rosie had been the most popular girl in high school, prom queen, homecoming queen and senior class president yet life was so miserable at home, she broke bones in her hands after her mother died so she could go the doctor and get nurturing from the nurses.

Her father took all her money and was a sexual predator, she revealed. 

Rosie O'Donnell, a close friend of Stern's, admitted to him that her father was a sexual predator and took all her money 

Donald Trump

Trump has been on the show more than 20 times – calling in or being in the studio because he was willing to say anything.

In 1997, he admitted to seeing a lot of women and when asked if he wore a rubber he said he hoped for the best.

'Well, I wouldn't say this but you could send a lot of people you really like to the doctor before you get to know them.

'It's a dangerous world out there. It's sort of like Vietnam – the V era,' Trump said. 

'It is my personal Vietnam. I feel like a great and very brave soldier. This is better than Vietnam. It's more fun', the now-President confessed.

'The perfect date: Meet at 7 for drinks. Then you promise to take her out to dinner but you never get there. And the amazing thing is, you can have a second date around 8:30.

'Condoms? I don't know the name of it but I'm using 'em'.

Donald Trump appeared on Stern's show 20 times before becoming president, appearing with daughter Ivanka at one time

Kid Rock

'There's nothing f**king better than a plane. These motherf**kers that live in LA – I feel bad for these motherf*cking musicians who I think have money. You ain't got sh*t, motherf*cker.

With his 'big beautiful plane, a double wide in f*cking Nashville, a beautiful home in Michigan. I hunt in Alabama, I stay in Florida when it's f*cking cold in Michigan'.

'I've got a lot of problems. Money and p*ssy ain't one of em'.

'I've got a lot of problems. Money and p*ssy ain't one of em,' singer Kid Rock emphatically declared 

Arnold Schwarzenegger

Admitted that growing up in Austria after WWII, 'I was in such need to become somebody' – with starvation and surrounded by angry people who had just lost the war.

His parents thought that he was mentally ill because he hung posters of naked man on this bedroom walls – bodybuilding champions and boxers. Something he aspired to be.

Actor turned politician Arnold Schwarzenegger told Stern that growing up in Austria post WWII he was 'in such need to become somebody' 

Joan Rivers

'I call my vibrator Barbara Walters,' Joan Rivers declared to Howard Stern 

The comedienne was interviewed just five months before her untimely death.

Still angry that she was banned by Johnny Carson, she said, 'that moron Leno kept the ban up. He's a f**king a**hole. And I'm glad he's gone. He never made me laugh'. 

And as for Carson, Howard suggested he 'f*cked everything'. 

At 80, she admitted, 'I'm working better than ever, 'cause I don't give a sh*t about anything when I walk on that stage, I hate sitting down, Howard. I should have never let Judi Dench talk me into getting matching vagina piercings'.

'I call my vibrator Barbara Walters,' she declared.

'Even in your eighties you masturbate?' Stern asked.

'People who are dead masturbate. My doctor told me a ninety-six year old woman died and they found a saltshaker up there'.

Stern gave the eulogy at her funeral in Manhattan. He walked up to the podium, looked out and said, 'Joan Rivers had a dry vagina'.

'I know this because she told me. She told me that when she took a bath, her vagina was like a sponge and that all the water in the tub would get sucked in '.

Joan had been telling vagina jokes for years and would have loved it – according to Howard. 

HOWARD STERN COMES AGAIN: FULL EXCERPT

'I'm not proud of my first two books. I don't even have them displayed on my bookshelf at home. I think of them, and of the interviews I did with my guests during those first couple decades of my career, and I cringe. I was an absolute maniac. My narcissism was so strong that I was incapable of appreciating what somebody else might be feeling.

'I have so many regrets about guests from that time. I asked Gilda Radner if Gene Wilder had a big penis. Great question. Drove her right out the door. George Michael's band Wham! Everyone I worked with said, "Whatever you do, don't ask them if they're gay. Do not ask them if they're gay." Within twenty seconds, I asked them if they were gay. Eminem came on the show once then never again. Same with Will Ferrell.

'Possibly my biggest regret was my interview with Robin Williams. When Robin came on the show in the early nineties, I spent the entire time badgering him about how he had divorced his first wife and remarried his son's former nanny. I was attacking the guy, and he was justifiably furious with me. Years later, I realized I finally needed to apologize. I had already done this with some other people. I called them and tried to make amends. Some were gracious. A radio guy I had been awful to said, "You know what, man? I'm so glad you called. I actually felt bad for you that you were carrying around so much bitterness and ugliness inside, and I'm happy you don't have that anymore." Others were angry. A famous comedian I had bashed said to me, "I appreciate that you called, but I don't know if I could ever forgive you. I had to go through a lot of misery, because your fans were brutal." I didn't know what Robin's reaction would be. He could have hung up on me. He could have cursed me out. I had to do it.

'It took me twenty years to work up the nerve. I was in the midst of tracking down his phone number, and the next day he died. I'm still filled with sadness over his loss and remorse for my failure to reach out sooner.

'Telling Carly Simon how hot she was for a half-hour or spewing sex questions to Wilmer Valderrama – this ultimately led to nothing. It wasn't good radio. It was meaningless. It was just me being self-absorbed and compulsive about asking something that would provoke and antagonize. Those weren't really interviews. They were monologues. Instead of a conversation, it was just me blurting out ridiculous things. I had some real issues.

'Then I started going to a psychotherapist.

'This was in the late nineties. I had no idea how therapy worked. The only thing I knew about it was what I saw in movies and on television, where people would just sit there and tell stories. So that's what I did. My first session, I sat down in the chair and began telling the therapist anecdotes as if I was on the radio. I hit him with all my favorite routines. I did a thorough and involved set on the Stern family tree, complete with impressions of my family. I put together a few minutes on marriage, then moved into the pressures of the radio business, and closed with the trials and tribulations of raising a family.

'After I was finished with my stand-up, the therapist instead of applauding said, "There's nothing funny going on here. Quite frankly, some of this stuff sounds pretty sad." My first response was to get defensive. Who was he to say that? I could tell that story and laugh. I had done it many times. Gradually, after a few more sessions, I realized he was right. He was the first person who ever said to me, "I take you seriously." I had always been hungry for someone to confide in like that, but I had pushed away my hunger. That's often what people who are traumatized do. In order to protect themselves, they act like nobody else matters. They tell themselves they don't need anyone.

'The irony is that I've always had an appreciation for others in my work. Yes, it's called "The Howard Stern Show," but I'm at my best when I have a bunch of people around me, when I can call on them and collaborate. Whether it's my co-host, Robin Quivers, or my producer Gary Dell'Abate or our jack-of-all-trades (sound effects, impressions, and so much more) Fred Norris; the staff of incredible writers and brilliant engineers; my front office, including chief operating officer Marci Turk and senior vice president Jeremy Coleman; my agent, Don Buchwald, and my executive assistant, Laura Federici; my bosses and the sales department at SiriusXM – I consider everyone a part of the team. What we do is like music, in a way. It's like a symphony. That is truly how I've always seen myself: as an orchestra conductor.

'Yet that generosity of spirit didn't extend to my guests. I should have treated them as talented soloists and welcomed them to join in our performance. I was just too afraid that the audience would be bored when they didn't get their fix of outrageousness – as if some quiet notes would have destroyed the concerto. Everything had to be one loud, crashing crescendo.

'Initially, I went to therapy twice a week. Then the therapist had me up it to three times. Eventually he recommended I make it four. I thought, "Man, I didn't know I was that screwed up." I was reluctant to make such a big commitment, but I did it. I completely gave myself over to the process.

'The more I went, the more that translated into how I interviewed my guests. I found myself changing my approach because I had experienced what it was like to have someone genuinely interested in my life. Therapy opened me up and enabled me to appreciate how fulfilling it was to be truly heard. That led me to the thought: "You know, somebody else might actually have something to say. Let's just sit here and listen and not make it all about you."

'At first, not making it about me was difficult. I had to learn to say no to myself. Stop talking. Start listening. Let someone else shine and have a moment. Trust that the audience will remain there.'

Excerpt from Howard Stern Comes Again by Howard Stern. Copyright © 2019 by One Twelve, Inc. Published by Simon & Schuster, Inc. on May 14.