VIDEO: Conan O’Brien Asks Howard About the Art of Conversation and His Broadcast on 9/11

Howard recently appeared on Conan O’Brien’s podcast “Conan O’Brien Needs a Friend,” sitting down for a wide-ranging interview just a few weeks after the late-night host had graced the Stern Show with his presence.

The legendary broadcasters tackled a variety of subjects during their second conversation, discussing everything from the dying art of the long-form conversation to Howard’s best-selling book “Howard Stern Comes Again.”

“The mistake that people can make is they can think the strippers, and the vibrators, and the, you know, little people, that that represents pushing the envelope … but at a certain point sitting down and having a conversation with someone is edgier than if you had sixty-five strippers come in here right now,” Conan told Howard.

Howard agreed. “Those kind of conversations to me are way more satisfying,” he said. “This is what I’m most proud of, these conversations. What this book represents to me is a collection of my best stuff.”

Howard has been open about his evolution as a broadcaster and interviewer during his recent book tour, but from Conan’s perspective the King of All Media’s maturation may have been foreshadowed years earlier during Howard’s famed Sept. 11, 2001 broadcast.

“I always thought that’s a moment that—against your will, maybe prematurely, maybe you were ready for it, but you didn’t want it—you were forced into this situation that you had to take us all through this day,” Conan said.

“It was an advanced look at where you were going,” he added.

Check out more of Conan and Howard’s conversation (above) and listen to more “Conan O’Brien Needs a Friend” here.