Howard Stern's Secret: How the Fiercely Private Star Convinces Hollywood to Reveal Just About Everything

If you still think he's only about the naked women and the art of the "shock," you haven't been paying attention

By Natalie Finn Jun 22, 2017 6:30 PMTags
Gwyneth Paltrow, Howard SternHoward Stern Show

If you still think that Howard Stern is only all about the naked women and the art of the shock just to be shocking, then you haven't been paying attention.

Because while, yes, the phony phone calls continue and the Wack Pack remains a topic of much conversation, the broadcasting pioneer has stealthily become the most probing, substantive interviewer of celebrities—including the stars whom you would never imagine having the wherewithal to sit down with him, knowing the conversation is going to get personal and then some.

"That's me!" Gwyneth Paltrow told E! News a couple years ago after her first-ever interview on The Howard Stern Show, during which she talked about, among many other things, her divorce from Chris Martin, her previous relationships with Brad Pitt and Ben Affleck, and her feelings about Martin dating Jennifer Lawrence. Needless to say, it was her first time publicly commenting on that last bit.

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"You know, normally when you do an interview, it's 10 minutes or one question so when you have an opportunity to talk and be yourself," Paltrow said. "I think myself was able to come out."

Indeed, the hour that Stern usually reserves for interviews is a key factor, allowing those who might be nervous time to relax or at least the proper amount of time to tell a story. The move to Sirius (now SiriusXM) in 2005 also made it infinitely easier to cut loose (never discount the jolt of taboo pleasure that comes from someone like Jimmy Fallon dropping an F-bomb), though the stars of TV, film and music have been opening up to Howard for decades.

After that hour is up they'll keep going so long as the guest has the time to spare. The encounters almost always end with a rep giving the high sign that it's time to go. More often than not Howard notes at some point toward the end of the interview, "You've said it all."


But even when they don't, chances are you've heard more than you ever have—all at once, not intermixed with a journalist's observations—from that person.

Which isn't to say that you sit down and instantly get peppered with personal questions. Stern, regardless of what the people who don't get him think, is a consummate professional—and a massive celebrity himself. He's also fiercely private, despite everything he's volunteered over the years about his childhood, his penis and his porn preferences.

While an actor or musician who doesn't feel like chatting much isn't going to go on in the first place, Stern does seem to abide by the unspoken (or sometimes vehemently spoken) tenets of interviewing: He won't go "there" if the guest doesn't want, so long as "there" isn't the only thing that's interesting about the person.

For instance, last year he and Hugh Grant, in what was their first meeting, touched on the actor's 1995 arrest, but Stern legitimately sounded super-uninterested in re-digging that one up. They had plenty of other things to talk about. And it's hard to say whether he didn't pointedly ask recent guest Jamie Foxx (making at least his third appearance on the show) about what's really going on between him and Katie Holmes, or if he was advised ahead of time to not bring it up—or if it just didn't interest him. 

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Because that's another thing Stern has increasingly incorporated as an interviewer over the past 10 years: he spends a lot of time on what interests him. Luckily, a lot interests him, including relationships, sex and setting the facts straight from gossip.

But he truly is interested in filmmaking, TV, the business of Hollywood, the songwriting process (he especially shines during interviews with musicians, who've ranged all over the map from Paul McCartney and Willie Nelson to Gwen Stefani, Lady Gaga and 21 Pilots, because he's a music lover and you can tell how intrigued he is by musical talent) and how these people feel about their success, their failures and whatever else has brought them to that point in life.

His Letterman-reminiscent descent into not giving too many f--ks about how he sounds also helps when it comes to being able to cover so many subjects—he bounces around at will. One second Ashton Kutcher was talking about the night he and Mila Kunis realized they were about to leave the friend zone and the next it was back to Kutcher getting his start by winning a local modeling contest in his native Iowa. They eventually got back to Mila and Ashton's inevitable coupling, but you can't help but scream at the radio a bit when Howard interrupts.

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There are also no boundaries anymore between Stern's neuroses and what he asks guests—half of his questions start with "isn't that just the f--king worst," "that had to be a horrible time for you," or did you fall into a major depression when...?" One rather pessimistic inquiry that comes to mind is when he asked Olivia Wilde whether she blamed herself when Cowboys and Aliens flopped at the box office. (She did not.)

Sometimes those interjections only sound half-serious—and he often admits he's only comparing how he would react in such a situation.

"I just can't walk out of here and say, 'I did a good show today and I'm very satisfied,'" Stern told Rolling Stone in 2011 about the insecurity that still plagues him despite his unequivocal success. "No, I gotta know, do you think I did a good show and are you satisfied? And that's the neurosis and that's the source of all problems for me."

The negativity can be distracting, but it also tends to result in more serious, self-reflective and—most importantly—lengthy answers, the kind that almost no talk show host has time to draw out these days. (Charlie Rose is of course an interview all-star, but those are 95 percent in-depth Q&As about the craft.) 

"The biggest criticism of my interviews is that I cut people off," he acknowledged to Rolling Stone. "I think my biggest asset is that I cut people off. It sounds like a contradiction, but the fact is you can't allow people to drone on. You are the orchestra leader. You are the one who is saying, 'My audience wants something new. I gotta keep it fresh.' I don't want my guests to bomb. My analysis is that a good interviewer not only asks the right questions but has sort of an inherent sense of what's interesting to this mass audience. And I don't know if you can teach that anywhere."

Courtesy of Kevin Mazur

Oprah Winfrey, Barbara Walters and Diane Sawyer have all presided over memorable interviews, but rare was it afterward that you had an entirely new appreciation for an actor or artist as a person, or saw them in an entirely new, positive light. You'd hear some revelations, sure, but you still liked who you were going to like, and you were still creeped out or put off by whomever you were going to be irked by anyway.

Thanks to the candor and honesty a guest pretty much has to exhibit on Howard's couch, and almost always seemingly comes prepared to do, especially in recent years, people emerge from that session refreshingly human. They may not have talked about every skeleton in the closet, and plenty of people refuse to name names or dish the dirtiest of details, but the very act of going on The Howard Stern Show makes them instantly more likable. 

It somehow instantly indicates that they don't take themselves too seriously (excellent move, Gwyneth), or that they're done lying (strong decision, Lance Armstrong), or that they're not afraid of showing their real selves, even if their public persona demands them to be a certain way at almost all other times.

If Tom Cruise wants to really shed the cloak of weirdness that still trails him, 12 years after his Oprah interview, he should do The Howard Stern Show. Probably wouldn't be a bad stop for Anne Hathaway or Angelina Jolie, either...

You know what, it's a good idea for anyone who wouldn't mind being seen as a little bit more real. Obviously Mick Jagger isn't too concerned about such things, but he also happens to be Howard's current dream interview, now that David Bowie has passed away (a missed opportunity the host laments), so we encourage the Rolling Stones frontman to go for it ASAP.

Many guests have made multiple appearances—Foxx, Robert Downey Jr., Louis C.K., Sarah Silverman, Amy Schumer, the list goes on—and are well aware of Howard's ways by now. Others have admitted to being a bit nervous to sit down with Howard, but they usually end up saying they had a great time, or he's their favorite stop whenever they're on a press tour. Lady Gaga has said she loves visiting, and the result is always a meaty interview.

Even the major "event" interviews, such as Steve Martin or Madonna—whom Howard did rearrange his schedule for, so it's not as if there isn't a professional operation at work here—are momentous, but also produce the similar effect of both giving the biggest stars more time than usual to shine and of making these icons seem approachable.

And as Gwyneth Paltrow mentioned about her own experience, it seems that these celebrities also really appreciate the chance to be themselves, to clear the air, to set the record straight. Or, you know, just to chat.