In his new book, "Howard Stern Comes Again," the longtime radio personality reveals his softer side, and he details what he thinks are some of his most memorable interviews.
"Donald Trump, hands down, whenever you put him on the air, now, this is before he was running for president, he was an open book," Stern said. "He would say anything. And you know, oddly enough -- during the campaign and even now, people quote these interviews that I did with him."
"I was quite surprised, when they dragged out every single Donald Trump ... interview I had done. And in some ways, I felt it was unfair to Trump," Stern said, noting that he felt some of his quotes, such as "something to the effect that ... STD's were his personal Vietnam" were taken out of context.
"It was in a very joking scenario. He was not comparing his life to a Vietnam vet. It was 'Ha-ha-ha and this and that,'" Stern said. "When journalists took it and made it serious, I thought it was a little bit unfair."
Still, Stern said when the now-president would come on his show, "There was no filter."
When asked if he felt he in some way helped make Trump president, Stern responded: "Absolutely."
"I wanted to see Hillary Clinton win," Stern said. "If she had come on the show-- the way I helped Donald was I let him come on and be a personality. Whether you liked him or not ... people related to him as a human being."
"I wanted to do that for Hillary. The big knock against Hillary, especially with some of the male audience, was, 'Eh, we don't like her,'" he added.
Stern said he also thought that "Hillary Clinton's afraid of me, and justifiably."
"I thought that perhaps if she came on my show, we could've stripped away some of the pomp and circumstance or the tightness that comes with running for president and, like Donald, she could've been seen in a different light," he added.
As for his current relationship with Trump, Stern said it's not as warm as it used to be, especially after he turned down speaking at the Republican National Convention.
"It's a weird relationship I have," he said of Trump. "Donald was at my wedding ... I remember having very warm feelings for Donald, and I do. I mean, he was always very nice to me."
The Trump he sees in office, however, "I didn't know this was him."
The new Howard Stern
In an interview that ranged from boisterous to serious, Stephanopoulos quipped their conversation was "completely hijacked" by Stern, the self-proclaimed king of all media, who is used to asking the questions, not answering them.
Stern said his recent change of heart, and his inspiration to write the book, was a recent health scare that saw him diagnosed with kidney cancer.
When he went in for surgery, however, he said he found out it wasn't cancer, and said the whole ordeal, "all of sudden brought me to some kind of reality."
After intensive therapy and his Sirius XM show, Stern said he is a changed man, and at times embarrassed by who he used to be.
"You know, for years, I used to think, 'Well, I'm one type of person on the air. And off the air, I'm somebody else,'" he said. "But the truth was, that was me."
Stern said one of his most painful memories was an early 90's interview with the late actor Robin Williams, who he described as "one of the most magnificent human beings in the world."
Still, he recalls it as the "worst interview I ever did," recalling how he immediately grilled the comedian for a report that he was having an affair with his nanny.
As for the best interview of his career, Stern says it was his 2015 interview with Conan O'Brien, who opened up about his struggles with depression on the show.
"I was able to listen and not be trying to insert myself, I picked up on something he said. And then all of a sudden, he started talking about that he suffered from depression," Stern said. "And we kinda did this heavy thing ... It was like the cameras disappeared. The microphones disappeared. And the two of us were just locked in conversation."