Howard Stern ran the gamut from silly to profound on The Late Show, joining Stephen Colbert for a wide-ranging discussion that touched on psychotherapy, “wild” radio interviews with pre-politics Donald Trump and supporting Hillary Clinton for president in 2016. The self-proclaimed “King of All Media,” Rolling Stone‘s latest cover star, was on-hand Tuesday promoting his newly released book, Howard Stern Comes Again, which features career-highlight interviews and memoir-styled self-reflection.
After a suitably bizarre introduction in which he grabbed Colbert’s backside, did “the Robot,” banged on Late Show bandleader Jon Batiste’s piano keys and crooned about his book, Stern sat down with Colbert for the first time in the host’s Late Show stewardship and reflected on his former days as a judge on reality show America’s Got Talent.
“Here I was, Fartman — people were scared of me,” he said. “Children would run from me when I was in the room. Then I go on this family-friendly show, which I thought would be quite shocking — if I went on this show and I was like this teddy bear. So the weirdest thing happens: I start going to restaurants with my wife the first year America’s Got Talent is on, and suddenly people are coming up, [asking] ‘Can my kid sit on your lap?’ like I’m Santa Claus. And I go, ‘What bizarro world are we living in? Do these parents know what I do for a living?'”
Segueing back to the book and his secrets for a great interview, the DJ shared his memories of a “rather heavy discussion” he had with Colbert while interviewing the late-night host.
“You and I shared a moment in that interview that I’m very proud of,” he said. “You were talking about the death of your father … and your siblings, and it was heavy. I said to you, ‘What was it like to have a sad, depressed mother, and did you find it was a burden to have to cheer your mother up?’ You kinda stopped, and you said, ‘How do you know how to ask this?’ And I said, ‘Because my mother was depressed. She was very sad. She lost her mother when she was nine. She had really grown up in difficult circumstances. And I felt, as a kid growing up, there was no greater joy than in my life than to sit with my mother — and it gives me chills to think about it — and entertain her.’ The way I would entertainer is I would do impressions of all the mothers and fathers in the neighborhood for her — and all these conversations I would hear in her house. But I also realized when I went into therapy that this was a tremendous burden — I only wanted to make my mother laugh.”
Colbert dedicated an entire portion of the interview to Donald Trump, whom Stern interviewed “too many [times] to count” on his former radio program, The Howard Stern Show. “He was maybe one of the best, top-five guests of all-time,” Stern said of the future president. “Why? He was wild. I thought I was wild. He would come on and start assigning numbers to women, evaluating them, [rating them] 1 through 10 — who does that? … He would say anything that came into his mind. He was completely unfiltered. He was talking about [how] his daughter was the most attractive woman he’d ever met and how much he thought she was hot.”
Stern added that Trump privately called him “all through the [presidential] campaign.” “He wanted my endorsement,” he said. “As I say in the book, I’m a very big Hillary Clinton supporter. I liked Hillary Clinton very much. So Donald said, ‘Would you please come to the Republican convention and speak on my behalf?’ And I went, ‘Oh, my God.’ It’s a weird thing … who asks me to do something like that? Very nice, but I had to find a way to say, ‘I can’t do this.’ He knows I’m a Hillary Clinton supporter. I firmly believed that Donald did not want to run for president. I don’t think it was serious. I don’t think he wanted to be the president. I knew him. He had a great life at Mar-a-Lago. He was running around town. He played golf. He had a good time.”
Stern also maintained his theory that Trump never wanted to be president in the first place and only hoped to build his brand.
“I remember the first time he said, ‘I might run for president,’ he put out his first book,” he continued. “And I know some of the people involved in this, and they said, ‘Pretend like you’re running for president and you’ll sell a lot of books.’ And he did it, and it worked. Second book he put out, it was like four years later, and he said, ‘I might run for president.’ And again, he said, ‘I’m selling books, and it helps sell books.’ So what happens this time? He’s on The Apprentice, and the ratings are going down. NBC was balking at giving him a raise, so what did he say? ‘I’ll run for president. I’ll get a lot of press.’ And I really believe that this was a gimmick to get NBC to raise up his salary and keep The Apprentice on, and I would bet the farm on that.”
Stern added that endorsing Trump — and “[selling] out his complete beliefs” — would have offered one perk: “For little while, I said, ‘Wait a second, if I do endorse Donald and go all in … I could potentially be the Chief Justice of the Supreme Court — or the head of the FCC, which plagued me my entire career.”
Elsewhere in the interview, Stern lamented never getting to interview Clinton during her run for president. “I thought that if I did an interview with Hillary that she’d reach a new audience,” he said. “What if we could have talked about her humanity, why she got into public service. Here’s a woman who’s dedicated her whole life to public service. What was her life like as a little girl, growing up? What was her romance with Bill Clinton? What was she thinking when she was Secretary of State? What was she thinking when she was the First Lady? Was she saying to herself, ‘I wish I could be president, or was she satisfied with that?’ There’s a million questions I would have had for her that I think would have humanized her.”
The radio icon also opened up about the breakthroughs he achieved in psychotherapy. “I used to kind of laugh at and think, ‘Oh, I have it all together. I know what’s going on,'” he said. “And I equated my success with [thinking that I was] fine … But I’d gone through a divorce and had three young daughters at the time. I pushed myself into psychotherapy, and I’ve gotta tell you — I’m the poster-boy for psychotherapy. I think it’s terrific, and I got in touch with a lot of things about myself that I didn’t like. It was quite a journey.”