Like every great performance artist, interviewers are storytellers. Great personalities make interviews seem effortless. But they’re not for everyone. Not everybody can interview like Dan Patrick or, the King of All Interviewers, Howard Stern.

Having a great guest is a good start for a solid interview, but that’s no guarantee that the segment will succeed. I can’t remember hearing a dull Howard Stern interview. Ever. Stern has evolved from a shock jock to a thoughtful, compassionate, and multi-faceted host. His interviews alone are worth the price of a Sirius XM subscription for many subscribers.

What Makes Howard Stern the King of All Interviewers

It all starts with preparation and research. Despite how casual and spontaneous Stern’s remarks seem to be, his interviews are the result of a great deal of preparation. And Howard not only appreciates the preparation process, but he also seems to enjoy it. He says:

I don’t understand how any performer thinks they can just come on and wing it. And I don’t know why they would want to. There’s a great satisfaction and confidence that comes from preparing for interviews.

That point isn’t lost on Billy Joel, a regular guest on Howard’s show. Before his first appearance, the pop singer was worried that something outrageous would happen that could be embarrassing. Joel says:

Turns out I was wrong. He was completely unpredictable in a way I hadn’t expected. He knew more about my music than anyone I ever worked with in the entire radio industry. The interview Howard did with me was probably the most astute and insightful interview I’ve done in my 50-year career.

Wow. That doesn’t happen by accident. And it’s that type of preparation that makes him the King of All Interviewers and keeps guests and listeners coming back over and over.


Stern has earned his reputation for being unpredictable and outrageous, but there’s depth in his content. Listen to his interviews. He has respect for each guest. It doesn’t stop him from asking tough questions or leading them into uncomfortable conversations. But anyone he approves to be on the show is someone that Stern is interested in and/or admires.

And there’s a rhythm to the flow of a Howard Stern interview.

Intro: The introduction is always a compliment. Howard makes a little small talk and makes his guest feel welcome. Many first-time guests are nervous about being on with Howard, but he overcomes that anxiety and gains their trust quickly.

Well, look who’s here, looking all thin and beautiful. It’s the great [NAME]…

By warming up the guest, they feel safer. They’re loosened up and ready to interact with the King of All Interviewers.

The First Questions

In doing so, he makes them feel comfortable, easing into the conversation. He then quickly advances the break with an easy question.

The First Question: Many times, I coach personalities to start with their best question, as long as it’s not a challenging one. Stern takes a different approach. His first question is an extension of small talk. He’ll say something warm and friendly, like “How’s life treating you, my friend?” It gets the guest to start talking and establishes a rapport.

The greeting, followed by a quick personal question that’s easy to answer, takes only seconds. Now he’s ready to go to work.

The Real First Question: This is where Howard gets down to business. Here comes a direct question that captures a listener’s attention. It’s usually something complimentary to the guest, yet character-defining for Stern. Self-deprecation is a key part of his personality profile. Sometimes this question is about success or fame. Or sex (a part of Stern’s three-legged stool), depending on the guest.

For example:

Now that you’re a big star, how much action are you getting? Did you ever think you’d have sex this good?

The guests are sometimes embarrassed, but not surprised. After all, they kind of know this is going to come up. And so does the audience. It’s a benchmark of the show.

The Questions

Stern’s skill in getting guests to respond in ways they never have has made him legendary.  Howard has been described by some celebrities as a “truth serum”. He’s able to get to places few others can.

How does he do it? By asking direct, bold questions. And keeping it simple.

Daryl Hall of Hall & Oates fame says:

What Howard does is he asks intelligent, provocative questions. He goes there in a way that makes you comfortable with revealing a personal thing.

His ability to extract deep insight from guests transcends the appeal of the celebrity. Whether you’re a fan of Billy Joel or Daryl Hall is secondary to the story Stern tells through the questions and answers. The King of All Interviewers causes the audience to lean in to hear what will happen next, with high expectations that something interesting will emerge.

And it always does.

Going Deeper

It’s well known that Howard is known for being highly critical of himself. Along with that comes an aversion to criticism. There are no boundaries between Stern’s neuroses and the questions he asks guests. This is evident in the fact that almost half of his questions start with “Isn’t that just the worst,” “That had to be a horrible time for you,” or, “Did you fall into a major depression when…?”

One rather pessimistic inquiry came about when Stern asked Olivia Wilde whether she blamed herself when Cowboys and Aliens flopped at the box office. (She did not.)

The negativity can be distracting at times, but also tends to result in more serious, reflective, and lengthy answers. This is the kind of response that almost no talk show can get to.

Stern tells Rolling Stone magazine:

The biggest criticism of my interviews is that I cut people off. 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. I gotta keep it fresh. I don’t want my guests to bomb. A good interviewer not only asks the right questions but has sort of an inherent sense of what’s happening to this mass audience. And I don’t know if you can teach that anywhere.

Paul McCartney Opens Up

His pointed questions are unusual, often the first time that guest has ever been asked it. Steve Goldstein of Amplifi Media points out that in one of his many interviews with Paul McCartney (he’s had Paul on several times), Stern asked the simple question that any Beatles fan has probably wondered but never thought of as a question.

He asked Sir Paul:

What caused you to come up with a song like Why Don’t We Do It In The Road?

McCartney was taken by surprise. He laughed, clearly taken off-guard, and said:

In all the interviews I’ve done, that’s the first time I’ve been asked that question.

He went on to tell a fascinating story about the song. A great question took a guest off-guard and turned into an amazing moment on the air.

Okay, now you’re curious about the story. It was while the Beatles were in India with Maharishi Mahesh Yogi. Paul says:

There was a male monkey hop on the back of this female and gave her one, as they say in the vernacular. Within two or three seconds he hopped off again and looked around as if to say “It wasn’t me!” and she looked around as if there’d been some mild disturbance. And I thought, ‘that’s how simple the act of procreation is’. We have horrendous problems with it, and yet animals don’t.

Listen and Respond

But as great as Howard’s questions are, Stern’s follow-up is better. This is where he shines. He doesn’t ask a question, then start thinking about the next one on his list. In fact, he may never get to some of the questions he had planned.

The King of All Interviewers listens to the answer. Then he responds.

Actress Emily Blunt had a rocky relationship with Michael Buble’. She’s now married to John Krasinski, but Stern was more interested in her past. He wanted to get to the details of a story about dating Buble’ because it had never been told.

Howard warmed up his guest, then confronted Blunt, starting with a friendly question. He said:

You haven’t dated a lot of guys. I know you like monogamy. And you were madly in love with Michael Bublé. Emily, what happened?

Inserting her name into the end of the question (“Emily, what happened?”) made the exchange more intimate. It was like a friend confiding in a friend.

Blunt laughed nervously and answered his questions. But she focused on how much she loved Michael’s family. She wouldn’t dish the dirt. Stern listened, then responded. That’s when he brought up the rumors of cheating.

Stern: But was he faithful?

Blunt: It’s complicated … I’m going red! … I never want to talk about it.

Stern: You want me to give you closure? Pretend right now I’m Michael, and talk to me about what went wrong, and I’ll answer you as Michael.”

That’s courage. And that’s just another reason he’s the King of All Interviewers.


Listen to or watch (on YouTube) his interviews and you’ll quickly understand why guests say Howard is a truth serum. His reputation has caused publicists and PR companies to encourage clients to be on his show if they want to make an impact. Most of the time, an appearance on Stern turns into news that is spread through social media and onto entertainment sites worldwide.

Howard is a glowing role model, but don’t copy the style. Adapt the principles of that make him the King of All Interviewers. Make guests feel comfortable, ask simple and direct questions and listen and respond. It’s a great formula for creating amazing interviews.

Photo Credit: Boston Herald

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