Howard Stern discusses new book, 'Howard Stern Comes Again'

“It's been over twenty years since my last book, and I vowed I would never do this again.”

So begins “Howard Stern Comes Again” (Simon & Schuster, 560 pp., $35), the talk show host’s first literary effort in 24 years, actually. It goes on sale today.

In the introduction, Stern, 65, explains that lifelong OCD and the pressures of other gigs — the Sirius radio program, his former role as host of “America's Got Talent” — had ruled out another book. Then, in the spring of 2017, he writes, “Simon & Schuster handed me a finished copy. Tricky bastards.”

The publisher's idea was this: dozens of interviews from “The Howard Stern Show" over the years, each with a Stern-written preamble. Stern didn't like the interviews S & S had selected, so he chose his own — 39 of them, most from Sirius, which he joined in 2006, and a handful from the old terrestrial radio days. Some interviews with Donald Trump — there were dozens over the decades — are included as part of a recurring segment called “And Now a Word from Our President.” Other interview subjects include Madonna (2015), Harvey Weinstein (2014), Joan Rivers (2014), Jay-Z (2010), Billy Joel (2014) and David Letterman (2017).

One revelation will surprise longtime fans: Stern writes that he had a cancer scare in 2017, although subsequent surgery revealed that he had a benign cyst on one of his kidneys.

I spoke recently with Stern about the book, that colorful past and the immediate future. The conversation has been edited for length and clarity.

Other than the health scare, is there anything in these pages that will surprise fans?
I didn't think of sitting down and shocking readers with revelation after revelation. It was more about psychotherapy, which was the hardest part for me — to come up with a better and more balanced life. I was falling apart on the inside [in the late '90s]. This was where I could say that I think psychotherapy works and that we lose sight of that, especially with the male audiences that sometimes think my opening up is ridiculous, or that therapy is all nonsense or a racket. I think change is possible.

Nothing in your life is particularly secret, so why keep the health scare from fans until now?

There's this whole internet culture [where you say], “Hey, my nose is running,” and the next thing they're doing is telling you stories about a friend's nose which was also running and how he ended up dead two weeks later. I'm a bit of a hypochondriac and worrier, so the real reason is that I didn't want to hear from anybody who had a similar operation. I [thought] I had cancer. It was 95 percent [certain]. I was in shock.

One of the more interesting reveals is the interview that never happened — Hillary Clinton — and how aggressively you pursued her.

I never pursued a guest [until her]. I really felt I could have made a difference with Hillary. As I explain in the book, I think there's a simple lesson in life — not to tighten up to the point where you close yourself off. She needed to appeal to a segment of my audience, a male part of my audience, that just [expletive] couldn't stand her. I don't know what it was, but as was pointed out [in a New York Times profile], I am able to present people in such a way on the radio where you strip away whatever it was that bugged people about them and get to hear the [real] person.

You argue that she made a mistake by not coming on.

Well, look at how the election turned out. It came down to a few thousand votes in a few key states. I could have made a difference. I'm not implying I could have changed the election, but I could have made a dent. It may have had an impact. [Not getting the interview] was a great disappointment to me.

How far did negotiations get with her?

There were a whole bunch of conversations [with handlers], but I think she thought she had [the election] locked up. But you can't ever think you have anything locked up. The other thing is, Donald Trump is good at talking like a dude. He's tremendously effective at it, and I wanted her to come on and talk authentically, and I think that could have been achieved.

You certainly helped “humanize” Trump over the decades.

That is my goal — to humanize people. He wasn't running for president, remember, at the time, he was a New York businessman. And he was one of those guests who came on and knew how to play. A lot of the media now are trying to use those [old] interviews politically, like when he agreed that maybe his Vietnam — his personal Vietnam — was STDs. But it was a joke, and he wasn't saying it in a serious way. But of course [the interviews] humanized Donald. We have fun with people in this environment where anything goes.

I imagine everyone who reads this will be surprised to learn your favorite interview in your career: Conan O'Brien?

So far I think it was my greatest. He was just so authentic, a great guest and it was one of the first times when I didn't beat myself up afterward. I always think I screwed up. With Conan it was different. I just felt like I was connected to him. I felt like we were friends. I get seduced. You think, gee, Conan and I should be friends. He was fantastic.

You express regrets about the old Howard, but are you ashamed of him?

Ashamed? No, absolutely not. I think I'm a better performer now and like the way I sound now more than then. But no — that radio show was groundbreaking and was right for the times. I came out of the ‘60s. I love the punk era of “[Expletive] everything and [expletive] you. You have a problem with that?” It is something I'm proud of. That was groundbreaking radio.

You get wistful in the interviews with Jon Stewart and David Letterman, both in semiretirement when you talked to them. Ever think about when you'll hang it up, too?

I honestly don't know. I got two more years on the contract. I'll certainly honor that. But it is getting harder and harder to do [the show]. Sometimes I think — I don't know — part of myself says to keep doing this, and there's a part that says to walk away. I've been hustling my whole life, but to sit back and relax? I don't have a definitive answer.