One of my proudest moments in marketing was when I got my company 20 minutes of free airtime on “The Howard Stern Show.” We were a radio marketing agency, had just named a hypothetical radio industry “Mount Rushmore” onto which Howard’s face was chiseled, and were invited to his show to give him a plaque. It was marketing heaven — millions of listeners and a free swing at anything we wanted to say to promote ourselves. The show’s producer couldn’t have been more helpful: “What would you like Howard to ask your boss?” he asked me.

My boss, however, instead of simply answering Howard’s questions about who we were and what we do, tried to be funny and wasn’t. He wasn’t going to “out-Howard” Howard. Howard, meanwhile, who began the interview humble and gracious, tried his best to be accommodating but in the end couldn’t help himself, reverted to his well-known persona, and proceeded to eat him alive.

I probably didn’t realize it then, but that incident, despite its outcome, was catching Howard at a time of personal transition from outlandish shock jock to a kinder, gentler, compassionate entertainer. This shift in maturity is well documented through his own observations and favorite celebrity interviews that comprise his just-released third book, “Howard Stern Comes Again” (Simon & Schuster).

The book is a collection of 50 interviews covering everything from sex, relationships, money, fame, spirituality and success. For example:

Tracy Morgan opens up about his near-fatal car crash.

Lady Gaga divulges her history with cocaine.

Madonna reminisces on her relationship with Tupac Shakur.

Bill Murray waxes philosophical on the purpose of life.

Jerry Seinfeld offers a master class on comedy.

Harvey Weinstein denies the existence of the so-called casting couch.

And much more.

Along the way, Howard undergoes a transformation. “At first, not making it about me was difficult,” he writes. “I had to learn to say no to myself. Stop talking. Start listening. Let someone else shine and have a moment.”

Howard recalls how he used to be addicted to over-the-top comments and convinced that was the only way to stay in business. “I should have treated (my guests) like talented soloists and welcomed them to join in our performance. I was just too afraid that the audience would be bored when they didn’t get their fix of outrageousness.”

Throughout the pages, readers learn about:

Howard’s favorite interview: “Conan O’Brien talks openly about his longtime struggle with depression. I don’t think he’d talked about it much before this.”

His biggest regret: “My interview with Robin Williams. I was attacking the guy and he was justifiably furious with me.” It took Howard 20 years to get up the nerve to reach out and apologize, and as he was tracking down Robin’s number, he learned of his death.

Discussing sex on the radio: “Honest to God, I didn’t do it to shock people. Not at first. But when I saw how outraged people were…I absolutely had to run with it.”

On evolving as an interviewer: “On terrestrial radio, my interview technique was like bashing someone in the face with a sledgehammer…Now when a guest comes into the studio, I imagine they are sitting at dinner with Beth and me. I try to be polite and warm them up…before delving deeper and asking them more probing questions.”

The interviews, Howard believes, represent not only his personal evolution but the evolution of pop culture over a quarter of a century: Madonna to Gaga; McCartney to Ed Sheeran; Letterman to Colbert; Rosie O’Donnell to Ellen DeGeneres; Joan Rivers to Amy Poehler.

“It’s not just the evolution of entertainment but of society as a whole.”

With a career such as his, it’s touching to hear him say, “These in-depth interviews – that’s what I’m most proud of. It’s one of the things I want to be remembered for before I die.”

Howard Stern, the great listener. Indeed!

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