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Howard Stern opens up to Colbert about "wild" Donald Trump and his infamous comments on daughter Ivanka

How Howard Stern became a new man

Stephen Colbert welcomed the self-declared "king of all media," Howard Stern, on "The Late Show" last night, and the shock jock divulged several details about his experience interviewing the "wild" Donald Trump, the 2020 presidential race, and what first got him into entertainment.

It took a few minutes for Colbert to get Stern into his seat — the radio host first wanted to sing an impromptu song with the band about his new book, "Howard Stern Comes Again."

Once he got him to sit down, Colbert complimented Stern's interviewing skills, and Stern revealed what made him such an entertainer. When he was a child and his father died, he felt a need to entertain his mother and make her laugh, he said.

The pair of hosts then talked about one of Stern's most-interviewed guests: Donald Trump. "I would have Donald Trump on — and I say it in the book — and he was maybe one of the best guests of all time. And why? He was wild," Stern told Colbert. He named Mr. Trump's affinity to rating women on a scale of one to 10 as one of the things that gave him that impression.

"I'm like, 'Who does that?' It was pretty wild," Stern said to boos from the audience.

"But [he was] a great guest because he would say anything that came into his mind," Stern said. "He was completely unfiltered, he was talking about [how] his daughter was the most attractive woman he ever met and how much he thought she was hot." The crowd booed again at the mention of Mr. Trump's infamous, inappropriate comments about Ivanka on Stern's show.

Stern also divulged that the last time he spoke to Mr. Trump was during the 2016 campaign. Then-candidate Trump asked Stern to speak on his behalf at the Republican National Convention — despite the fact that Stern was a known Hillary Clinton supporter.

Trump Wanted Howard Stern To Speak On His Behalf At The RNC by The Late Show with Stephen Colbert on YouTube

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Stern joked that he did consider "selling out his complete beliefs" and endorsing Mr. Trump — with the hope that if he did so, he'd be appointed to the Supreme Court or FCC, or at the very least, get a trip to Camp David. 

With over four decades in entertainment, Stern has interviewed countless celebrities, but there was one "white whale" he couldn't get on his show: Hillary Clinton. Ultimately, Stern, who supported Clinton's campaign, did not manage to book her on his show during the 2016 presidential election. 

"Do you think it would've made a difference if she had come on your show?" Colbert asked.

"Hillary? I do," Stern said. "I'll give you my theory on this. I thought if I did an interview with Hillary, maybe she would've reached a new audience." Stern said he has 33 million subscribers on Sirius XM and he reached audiences Clinton might not have reached on her own. 

Had Clinton come on his show, Stern said he wouldn't have necessarily asked about politics, but rather, her life public service. 

"I want to say to anybody now who is running as a Democrat: Donald Trump, I saw it on my show, he knows how to communicate with people," Stern said. "And you can mock him, you can say all the goofy stuff you want to say about the guy, but when he would come on my show, he knew how to connect — not with the whole audience of the country, but with all people." 

"I firmly believed that Donald did not want to run for president. I don't think he was serious. I don't think he wanted to be president. He had a great life at Mar-a-Lago," Stern said about his old pal. During the 2016 campaign, Stern thought Mr. Trump ran to get higher ratings for "The Apprentice."

"He is so shallow you could not get your ankles wet in him," Colbert joked.

Howard Stern: What If Hillary Came On My Show In 2016? by The Late Show with Stephen Colbert on YouTube

As for the candidates Stern is most interested in having on his show now, he said why not Joe Biden, who has had "a fascinating life." Stern also said he would like to have Bernie Sanders on. 

"Bernie Sanders is probably my biggest hero for one reason — and this is very self-serving." Stern said. "When the FCC was attacking me and they were attempting to take me off the air... Bernie Sanders got up in the Senate and said 'I think what you're doing to Howard Stern is unfair. I believe in freedom of speech, and I want to go on record in saying you got to stop it,'" Stern told Colbert. He said this occurred in the 1990s, when he thought his career was over.

Colbert's wide-ranging interview with Stern played out over about 25 minutes. Unfortunately for the talkative Stern, unlike his own show Colbert's had to take commercial breaks. 

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