There are also no boundaries anymore between Stern's neuroses and what he asks guests—half of his questions start with "isn't that just the f--king worst," "that had to be a horrible time for you," or did you fall into a major depression when...?" One rather pessimistic inquiry that comes to mind is when he asked Olivia Wilde whether she blamed herself when Cowboys and Aliens flopped at the box office. (She did not.)

Sometimes those interjections only sound half-serious—and he often admits he's only comparing how he would react in such a situation.

"I just can't walk out of here and say, 'I did a good show today and I'm very satisfied,'" Stern told Rolling Stone in 2011 about the insecurity that still plagues him despite his unequivocal success. "No, I gotta know, do you think I did a good show and are you satisfied? And that's the neurosis and that's the source of all problems for me."

The negativity can be distracting, but it also tends to result in more serious, self-reflective and—most importantly—lengthy answers, the kind that almost no talk show host has time to draw out these days. (Charlie Rose is of course an interview all-star, but those are 95 percent in-depth Q&As about the craft.)

"The biggest criticism of my interviews is that I cut people off," he acknowledged to Rolling Stone. "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. You are the orchestra leader. You are the one who is saying, 'My audience wants something new. I gotta keep it fresh.' I don't want my guests to bomb. My analysis is that a good interviewer not only asks the right questions but has sort of an inherent sense of what's interesting to this mass audience. And I don't know if you can teach that anywhere."