The Most Shocking Things Donald Trump Ever Revealed to Howard Stern

Before he became the president, Donald Trump was a reality TV star and a businessman who fascinated many Americans. He was also known for saying some vulgar and surprising things, sometimes about his own children.

But no one could get The Donald to make shocking statements quite like Howard Stern. Trump has been interviewed more times by Stern than by any other TV or radio personality, and he never held back.

Trump and Stern’s History

Howard Stern

Howard Stern | Dave Kotinsky/Getty Images

Over the course of two decades, Trump was a guest on Stern’s show about two dozen times. Stern asked him all kinds of questions, with topics ranging from his sex life and marriages to his children and even a few political issues. Having no idea he’d one day run for office, Trump told all, and some of what he said is pretty shocking.

Next: Did Trump have a crush on a famous princess?

Trump thinks he could have slept with Princess Diana

Trump hinted that he slept with Princess Diana. | Fox Photos/Hulton Archive/Getty Images

Stern once asked Trump to clarify his statement that he could have slept with Princess Diana.

“I think I could have,” Trump responded uncertainly before going on to praise Diana’s appearance.

Next: Let’s talk about the shocking Ivanka-shaped elephant in the room.

He joked sexually about his own daughter

Donald Trump kisses his daughter Ivanka Trump

Trump objectified Ivanka on Stern’s show. | Brendan Smialowski/AFP/Getty Images

While it’s no secret that Trump adores his daughter, Ivanka, many people think his comments about her body are disturbing. Not only did he allow Stern to refer to Ivanka as “a piece of ass,” he called her “voluptuous” and talked about her figure and her breasts.

Next: Trump revealed his family’s dirty laundry.

He admitted his older children tried to cut Tiffany out of his will

Donald Trump Jr., Donald Trump, Tiffany Trump and Ivanka Trump in 2006

Trump claimed that Don Jr. and Ivanka tried to keep her out of his will. | Michael Buckner/Getty Images

Tiffany is Trump’s daughter with his second ex-wife, Marla Maples. In one interview with Stern, Trump admitted that Donald Trump, Jr. and Ivanka weren’t thrilled about their new sibling and wanted to omit her from her rightful inheritance.

Next: A public audience won’t stop him from groping his wife.

He confessed he gropes Melania in public

Trump claimed to grope Melania in public. | Paul Hawthorne/Getty Images

Stern had many questions about Trump’s relationship with his current wife over the years, once directly asking him if he ever gropes her in public.

“Yeah,” Trump said.

“Yeah, as I know,” Stern replied.

Perhaps that’s why Melania sometimes swats her husband’s hand away in public.

Next: Our current president has said some tactless things about women.

He claims it’s ‘hard to be a 10’ if you’re flat-chested

Donald Trump crowns the new Miss USA Nana Meriwether (C) alongside newly appointed Miss Universe Olivia Culpo (L) in 2013

Donald Trump spent a lot of time objectifying women on the Stern show. | Timothy A. Clary/AFP/Getty Images

Of the many (many) comments made about women’s bodies on Stern’s show, Trump was once quoted as saying “I view a person who’s flat-chested as very hard to be a 10.” This came after Stern asked him to rank famous women based on their looks.

Next: The sexism runs deep with this one.

He said he didn’t do anything to help raise his kids

Trump's family at his campaign announcement

Trump bragged about his hands-off approach to parenting. | KENA BETANCUR/AFP/Getty Images

In 2005, Trump told Stern, “I like kids. I mean, I won’t do anything to take care of them. I’ll supply funds and she’ll take care of the kids. It’s not like I’m gonna be walking the kids down Central Park.”

Next: Even pregnancy didn’t spare this Kardashian from Trump’s judgment.

He slammed Kim Kardashian’s pregnant body

n this handout photo provided by Forum Photos, Among the VIP guests of Managing Partner, Shelli Azoff, and Ariana Grande's manager, Scooter Braun,

Trump called Kim Kardashian “large” while she was pregnant. | Rich Fury/Forum Photos via Getty Images

After telling Showbiz Tonight that Kim Kardashian was a “nice person” who had “gotten a bit large,” Trump went on to slam her on The Howard Stern Show.

“Does she have a good body? No. Does she have a fat ass? Absolutely,” he said in 2013. Kardashian was pregnant at the time.

Next: Trump’s views on same sex marriage are pretty hypocritical.

He said same-sex marriage is ‘not his thing’

Marriage equality isn’t “his thing.” | Drew Angerer/Getty Images

Most people assumed Trump was in favor of marriage equality. But despite having two failed marriages himself (and committing adultery in all three unions), Trump told Stern in 2013 that he was not supportive of same-sex marriage, surprising Stern.

In March 2011, he told Bill O’Reilly, “I just don’t feel good about it. I don’t feel right about it. And I take a lot of heat because I come from New York.”

Next: But he was, in fact, in favor of the war on Iraq.

Those three little words: ‘I guess so’

He had a tepid response to the invasion of Iraq. | Alex Wong/Getty Images

Despite constantly stating that he’d always opposed the invasion of Iraq during his 2016 campaign, Trump once told Stern that he actually did support it.

“Yeah, I guess so,” Trump said in 2002 when asked by Stern if he supported the invasion. “You know, I wish the first time it was done correctly.”

Next: Trump wasn’t shy about his love of younger beauty queens.

He peeked at naked beauty queens during pageants

The top five finalists in Miss Teen USA 2016 join hands

Trump used to go into dressing rooms at beauty pageants. | Ethan Miller/Getty Images

The Trump campaign repeatedly insisted that he never misbehaved during his Miss USA and Miss Universe pageants, Trump bragged to Stern in 2005 about going backstage when contestants were naked.

“No men are anywhere, and I’m allowed to go in, because I’m the owner of the pageant and therefore I’m inspecting it. … ‘Is everyone OK?’ You know, they’re standing there with no clothes. ‘Is everybody OK?’ And you see these incredible-looking women, and so I sort of get away with things like that.”

Next: Trump wasn’t always crass when talking about his wife.

The Donald fully trusts Melania

Donald Trump and then-girlfriend Melania Knauss, 2002.

Trump contrasted Melania with his ex-wife. | MATT CAMPBELL/AFP/Getty Images

In an interview with Stern in January of 2004, Trump had some kind things to say about his third wife, Melania.

“I know she’s faithful,” he bragged, adding “I trust her in every way.” In previous interviews he’d called her “perfect” and “a very nice person,” so the praise seemed genuine. Unfortunately, it came at the cost of comparing her to his second wife.

Next: Trump wasn’t thrilled when he learned his ex-wife was pregnant.

Trump wasn’t happy about Marla Maples’ pregnancy

Marla Maples and Donald Trump

Trump was not happy when he found out Marla Maples was pregnant. | Diane Freed/Getty Images

In the same 2004 interview, Trump confessed that his news to his ex-wife Marla Maples’ pregnancy wasn’t positive.

“But, you know, at the time it was like, ‘Excuse me, what happened?,’ Trump said, adding,  “And then I said, ‘Well, what are we going to do about this?’ [Marla] said, ‘Are you serious? It’s the most beautiful day of our lives.’ I said, ‘Oh, great.’”

He did go on to say he was glad it happened and that he had “a great little daughter, Tiffany.”

Next: Trump didn’t hold back when he was asked to rate celebrities’ looks.

Carmen Electra and Angelina Jolie clearly aren’t his type

Angelina Jolie posing

Trump wasn’t particularly kind to Angelina Jolie.| Michael Buckner/Getty Images

During one interview, Stern pressed Trump for his opinion on certain celebrities’ looks. Trump said Carmen Electra was an 8, claiming she looked better in photographs than in person and referring to her augmented breasts as “two light posts coming out of the body.”

He also expressed his displeasure with Angelina Jolie, saying he never thought she was good looking and that her lips were too big.

Next: How is Stern and Trump’s relationship now?

Here’s how the two men feel about all their talks now

Donald Trump and Howard Stern, 1997

Donald Trump and Howard Stern, 1997 | Dutton2013 via YouTube

Stern and Trump have been friends for decades, and Stern had admitted he never imagined Trump would become president. Stern also worries about Trump’s mental health, claiming that deep down, Trump just wants to be loved — and his fragile ego might not survive all the criticism.

Trump has expressed no remorse for his prior interview with Stern, explaining, “I never anticipated running for office or being a politician, so I could have fun with Howard on the radio and everyone would love it.” He added that he could say “whatever he wanted,” which he clearly still feels comfortable doing today.

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