Like every great performance artist, interviewers are storytellers. Great personalities make interviews seem effortless. But interviews are not for every performer. Few are able to interview like Dan Patrick, Oprah Winfrey, or the King of All Interviewers, Howard Stern.

Most think the key to a good interview segment is scoring a segment with a great guest. That is a good start, and it helps, but a great guest doesn’t make a great broadcast or podcast any more than a popular topic makes a great story.

The truth is that fans of a guest have already heard most of what that guest has to say. Non-fans aren’t that interested. The main challenge is to lead a conversation that reveals a part of the star that fans have never heard in such an interesting way that non-fans can’t turn it off.

I can’t remember a dull Howard Stern interview. Ever. Stern has evolved from a radio shock jock to a thoughtful, compassionate, and multi-faceted host. His interviews alone are worth the Sirius XM subscription.

Howard Stern Is the King of All Interviewers

So what is the difference, and what can aspiring interviewers learn?


Stern sounds casual, but his interviews are prepped, and Howard has learned to enjoy the process. 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. A great satisfaction and confidence 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. The interview was probably the most astute and insightful interview I’ve done in my 50-year career.

Part of the prep is selecting the guest. He respects each guest, or they aren’t invited on the show. However, that doesn’t stop him from asking tough questions or leading them into uncomfortable conversations.


There’s a rhythm to the flow of a Howard Stern interview. The introduction is always a compliment. Howard makes small talk to make 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]…

Once they feel safe, he quickly advances the break with an easy question, an extension of small talk. He establishes a rapport by saying something like, “How’s life treating you, my friend?”

This exchange only takes a few seconds. Now he’s ready for a direct question that captures the audience’s attention. Self-deprecation is a key part of his character profile. The question is usually about success, fame, or sex, 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 know this is going to come up and so does the audience. It’s a benchmark of the show.

The Questions

Guests have described Stern as a “truth serum” because he’s able to get them to talk about things few others can by asking direct, bold questions. He also keeps 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.

It doesn’t matter if you’re a Billy Joel or Daryl Hall fan. 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.

Howard is known for being self-critical, and he demonstrates his insecurities in the questions. Almost half of his questions start with “Isn’t that just the worst?” or “That had to be a horrible time for you,” or, “Did you fall into a major depression when…?”

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.

Listen and Respond

As great as Howard’s questions are, his follow-up is better. He doesn’t ask a question while thinking about the next one. He may never get to some of the questions on the list. He listens to the answer, then 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. He started with a friendly question:

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?”) was more intimate, like confiding in a friend.

Blunt laughed nervously and answered his questions. She wouldn’t dish the dirt but Stern listened, then brought up the rumors of cheating.

Stern: But was he faithful?

Blunt: It’s complicated … I’m going red! … I never wanted 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.

Example: Paul McCartney Opens Up

Steve Goldstein of Amplifi Media points out that in one of his interviews with Paul McCartney (Paul has been a guest several times), Stern asked a simple question that many Beatles fan never thought about. 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 to or watch (on YouTube) his interviews, and you’ll quickly understand why guests say Howard is a truth serum. An appearance on Stern’s show turns into news spread through social media and entertainment sites worldwide.

Howard is a great interviewer, but don’t copy his style. Study and adapt the principles that make him great.

It’s a great formula for creating amazing interviews.

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