Howard Stern warns the future presidential nominee: 'don't play it safe'

Stern talks about his interviews with Donald Trump, how an interview with Hillary Clinton could have changed 2016 and 2020 candidates.
3:06 | 05/16/19

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Transcript for Howard Stern warns the future presidential nominee: 'don't play it safe'
Let's talk about trump. He's heavily weighted in my book. There are 11 different interviews. The highlight of the interviews of trump in my opinion is the phenomenal fight he gets into on the air with A.J. They start yelling at each other and they're fighting over a woman. A.J. Had a girlfriend and trump was having sex with her and trump was on the air bragging that he stole a.j.'s girl and he was better than A.J. This was radio fireworks. He kept rating women during the interviews. Yes. I'm reading the book like why is trump rating women from one to ten. Because he's so hot sexually, he's so good looking that he's earned the right -- Now or then? Oh, have you seen him? I have. Unbelievable. What do you think of him as president? When we were covering him, a lot of his old interviews on your show were used for political fire comparing aides to Vietnam. I thought that was unfair. The aides to Vietnam, he was on the air joking. There was no way that was a serious comment. Having said that, look, I was a huge Hillary Clinton supporter. Not like oh she's the lesser of all evils. I was for her before Obama. I loved Obama, but I loved Hillary Clinton. I thought she was a candidate that was misunderstood. Her message wasn't coming across. This wouldn't have changed the election. I think if she would have come on the show -- I was begging her. I didn't talk to her directly. I think she was afraid of me and justifiably. She played it safe. That's the warning to whoever becomes the democratic nominee -- Who do you like? I don't know. There's so many people I'm on overload. It's like the flavor of the month. Biden is way ahead. Because I think people want a new president so badly that they want to play it safe. A guy who has been the vice president, he's tested. I feel bad for the women running. It's time for a woman to run, but because everyone is so nervous they're tightening up and saying it better be Joe The women are incredibly smart. Incredibly smart. There's a lot of good it was very awkward. Would you ever entertain a Republican? Absolutely. I voted for Republicans. Who? Locally -- You vote for bush? I did not. I voted for Pataki when he ran. In New York. In New York. I voted for -- I voted for Republicans. Can't think of any of them? No. I'm having a very hard time. I'm nervous. I see you getting yelled at all

This transcript has been automatically generated and may not be 100% accurate.

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