In a wide-ranging interview with The Hollywood Reporter published Wednesday, America's most famous "shock jock" revealed some details about his failed attempts to promote Hillary Clinton in 2016 and convince Donald Trump — with whom he's had a long-time professional and personal relationship — to pull out of the race.
The interview revolved around Stern's new book, which is based on "40 in-depth conversations, from the early and uncomfortable (Bill O'Reilly) to the more recent and evolved (Bill Murray); along with several dozen snippets that he'd weave together by theme, like sex and relationships or money and fame," THR explains.
Throughout the book, Stern interlaces excerpts from his over three-dozen conversations with Trump over the years, starting with them joking about Trump running for president in an interview back in 1995.
"[H]e'd also devote at least a few pages to the interview he tried desperately to land with Hillary Clinton, who, he'd reveal, had rebuffed him at every turn," THR's Lacey Rose notes. "Despite the host's history with the current president, who'd regularly call in and discuss such subjects as his sex life with Melania or his daughter Ivanka's 'very voluptuous' breasts, Stern was an ardent supporter of Clinton, both in 2008 and again in 2016."
But Stern could tell that his candidate of choice was failing to "connect" to voters in 2016 and expressed some regret in the interview that Clinton repeatedly refused to come on his show.
"His listeners span the country, he explains, and in that final stretch he could see that Hillary wasn't connecting with them," Rose writes. "Stern isn't arrogant enough to say for sure that an interview on his show could have tipped the election in her favor, but he doesn't rule it out, either." Rose quotes Stern as saying that a segment of his audience "really gets turned on to people they thought they hated because we tap into their humanity," pointing out as an example his audience's reversal on Lady Gaga after he brought her on.
Despite his vocal support of Clinton, however, Stern revealed that he couldn't stop himself from pushing back on those who were confidently proclaiming in 2016 that she would glide to victory against the brash business mogul.
"I'd sit there at these dinner parties and go, 'Not that you asked, but I don't think you're seeing this the right way,'" he told THR. "'Donald is communicating. He's talking like a dude. That's very powerful — take it from someone who knows.'"
After noting that Stern had once run for governor of New York in 1994 as a Libertarian but then pulled out "before it was too late," Rose notes that Stern tried to convince Trump to "do the same" both on- and off-air:
On-air and off, he had tried to get Trump to do the same. Early on, Stern was still fielding his calls from the campaign trail and spending time at Mar-a-Lago. Sure, he considered Trump among his greatest all-time radio guests — raw and unfiltered — but leader of the free world? He insists in those days, he never imagined Trump would get anywhere near that far, and he's convinced Trump didn't either. Save a brief congratulatory exchange when Trump won, the two haven't had any interaction since Stern declined his request to speak at the Republican National Convention.
As for that request to speak at the Republican National Convention, Stern said it was "difficult" to turn down "because there's a part of me that really likes Donald, but I just don't agree politically." If he was more "self-serving," he joked, he might be "the FCC commissioner or a Supreme Court justice by now."