What Larry King Taught Me About Interviewing

In 2011, I was in the seventh year of doing my comedy podcast, Comical Radio. It was the first podcast to feature interviews with comedians. By this time, I had done well over 1,000 interviews.

I was no stranger to hosting celebrities on the podcast. From George Carlin to Paul Giamatti to Janeane Garofalo and Kid Rock, I had talked to some pretty high-profile guests. But it wasn’t until an old, skinny Jew from Brooklyn walked into my studio that I really became a great interviewer.

To be honest, I wasn’t initially that excited about interviewing Larry King. My wife, Kylie Ora Lobell, booked him for me, and I knew that having him on my show could boost my download numbers. But I wasn’t a big Larry King fan. To me, the greatest interviewer of all time was and still is Howard Stern, who, especially back when I was growing up, would take crazy chances — at the risk of burning major bridges — to ask the questions everyone was afraid to ask.

In my young mind, Larry King was just a corporate shill for CNN who played it safe. Still, I was inclined to try and have some fun with the situation. I invited two comedian friends of mine, Esther Ku and Peyton Clarkson, to join me for the interview. Esther suggested we all wear suspenders in honor of Larry, which I thought was a great idea. She asked if she should write a song for him that might be a bit inappropriate. I loved that idea, too.

When Larry King came in, what took me by surprise was how incredibly comfortable he made me feel. I think he saw something in me that may have reminded him of himself. After all, a Jewish kid from Queens was making a go of being an interviewer and sitting across a Jewish kid from Brooklyn who had done it for years. It turned out we had a lot more in common than I thought. This became apparent as the interview went on.

As the interview progressed, I started to second guess if I should have encouraged Esther to write a song calling attention to Larry’s many divorces (and some things that maybe shouldn’t be written down in the Journal). But I’ve never been one to back down from a bit. So, I figured I would stick with the horse I rode in on.

When Esther did finally sing the song with a chorus — “Hey Larry King, Hey Larry King, when are you gonna buy me an engagement ring?” — instead of being giddy that we make might Larry King uncomfortable, I felt uncomfortable, because I’d really taken a liking to him in a short amount of time.

I don’t know what Larry King really thought of the song, but he was a good sport. I breathed a sigh of relief when he didn’t get up and leave but rather gave it a polite chuckle.

What really made that interview special, however, when that Larry King decided to impart some of his interviewing wisdom on me. He confided in me that he thought I was a very good interviewer, but I could become a great one with a few tweaks. He suggested making sure I keep the amount of “I’s” in the interview to a minimum, as it’s about the guest, not me. He told me I don’t need to say, “Can I ask you a question?” to my guests. He said if someone has agreed to be on your show, then it is already implied that you can ask them any question you want.

In response, I got vulnerable with him. I opened up about my insecurities as an interviewer. I told him that sometimes I’m scared that I’m going to look like an idiot because my guest will say something that goes over my head. I said I was never truly comfortable with my guests because of this fear. That’s when Larry gave me the single best piece of advice I ever received in my career: He told me that it’s OK to admit that you don’t know things. The audience will always forgive you for being ignorant as long as you are honest.

It’s OK to admit that you don’t know things.

That advice totally transformed the way I thought about my listeners. Up until that point, I thought they were all listening with the idea that they were out to get me as soon as I slipped up or showed any vulnerability. In my mind, they weren’t fans; they were judges. From then on, I saw the audience as empathetic comrades who wanted me to do well. With that one change, I was able to build my loyal fan base.

King’s advice gave me such a burst of confidence and a new appreciation for everyone I interviewed from that point on. It also changed the way I thought about the world. I started to see people in a kinder light.

For that, I will always be grateful to the legendary Larry King, whom I had misjudged before that day. In the time since I interviewed him, I have had the chance to go back and watch many interviews he’s done with a new sense of appreciation for his unique talent. To me, that talent was not necessarily the questions that he asked but his innate ability to disarm his guests with his incredible warmth and kindness.

Hey Larry King. I’ll miss ya.

Daniel Lobell is a comedian and the host of the pro-Israel talk show The Lions’ Den With Daniel Lobell from The Israel Group and the Doctorpedia podcast.