NEW YORK _ Shortly after clinching the Republican Party's presidential nomination, Donald Trump begged Howard Stern to speak at his convention _ but the infamous shock jock rebuffed the offer, noting he was a Hillary Clinton supporter.
Stern, who has interviewed Trump dozens of times, revealed the cringe-worthy exchange in an interview with David Letterman released Thursday.
"Well you know, it was a very awkward kind of thing, because Donald asked me to speak at the Republican National Convention," Stern, 64, told Letterman in the latest episode of his Netflix special. "I was put in a very awkward position of having to say publicly _ and to him _ that I was a Hillary Clinton supporter. I always have been, and I was honest with Donald. I said, 'Donald, you also supported Hillary.'"
Trump's relationship with Clinton has been profusely hostile since the 2016 campaign, but before he got into politics, he was both financially and personally cozy with Clinton, donating thousands of dollars to her New York senatorial campaigns and inviting her to his third wedding.
Stern, the self-proclaimed "King of All Media," said he struggled to understand Trump's change of heart after announcing his campaign.
"I really kind of felt, deep in my heart, that this campaign was really more about selling a book, or selling a brand," the radio titan said. "I didn't really understand that he would really want to be president."
Stern revealed that Trump would frequently phone him while campaigning.
"He would call me from the campaign trail very often, and say, 'Are you watching?'" Stern said. "I was tickled by this."
But even though he considered himself a "friend" of Trump, Stern stressed he was never a fan of his rhetoric.
"My politics are different," Stern said.
Letterman chimed in that Trump's presidency has gotten him weary for the future.
"I worry about it for my 14-year-old son," Letterman said. "When he's my age, what will we have around us?"
In a sneak-peak of Letterman's Netflix special released last week, Stern revealed that Trump frequently objectified his own daughter, Ivanka, while on the air.
During one particularly salacious discussion, Stern and Trump rated female celebrities by their looks on a scale from 1 to 10.
Unprompted, Trump declared, "You know who's a great beauty? My daughter Ivanka. Now, she's a 10."
