Howard Stern's most outrageous interview confessions: How Khloe Kardashian told him 'Once you go black you never go back,' Joan Rivers named her vibrator Barbara Walters and Madonna said Tupac Shakur 'got her all riled up'
- Radio host Howard Stern has written his third book, Howard Stern Comes Again
- The world's highest-paid radio host reflects on his controversial 30-year career in the new memoir
- He describes the most revealing interviews he has conducted with celebrities including Joan Rivers, Donald Trump, Khloe Kardashian and Jenny McCarthy
- Stern admits his unrelenting and crude questions to guests have left him feeling guilty, especially in his interview with Robin Williams
- He only realized years later that he needed to apologize to his guests after years of psychotherapy to understand his own narcissism, he writes.
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.