Regis Gets Letterman to Open Up in Rare Prime-Time Interview

David Letterman with Regis Philbin on CNN Tuesday night (Photo: CNN)

Sometimes it’s easy to forget how long David Letterman has been around.

And then he agrees to a rare television interview and you’re reminded that this guy has been in the TV business for so long that he ought to be placed on some kind of television Mount Rushmore.

Such was the impression formed from the interview Letterman, 65, granted to his friend Regis Philbin on CNN Tuesday night.

Philbin, 80, was subbing for the evening for Piers Morgan (on Morgan’s show, “Piers Morgan Tonight”) while Morgan takes a week off.

We all know Letterman’s been a late-night star for 30 years (marking that milestone just this year, as a matter of fact). So when he shows up in prime time to give rare insights into how show business works, then we always perk up and listen. Among the topics Dave and Regis covered: Dave’s relationships with Johnny Carson and Jack Paar, what it was like to appear on Carson’s “Tonight Show” for the first time, and Dave’s political leanings.

Here’s what Dave had to say about:

The last time he saw Johnny Carson, on Carson’s private yacht, for a cruise on the rivers around Manhattan:

Dave: The last time that I saw him . . . The way life is you don’t know that that will be the last time, that it turned out to be the last time. And it couldn’t have been a lovelier evening and I cherish that because it was — it was unusual. And it was my wife, myself, Johnny, and his wife on Johnny’s yacht that he had anchored in the Hudson. And it was a Friday evening and we sailed off just before sunset. And went up the Hudson up under the George Washington Bridge which is lovely.

Turned around, now the sun is setting. We go out to the Statue of Liberty and see that at night as the sky is darkening. And then you turn around and we headed up the East River, and you see the lower tip of Manhattan. And it was a sight and an experience like you'd never - you know, you never get to see New York like that.

And he was comfortable and we were chatting. And I knew that I always had - if the conversation got slow or there was an awkward moment, all I had to do is bring up Jack Benny.

Regis: He loved Jack Benny.

Dave: And I think he owed a great deal to Jack — his delivery and his mannerisms and his humor. And he would just start telling story after story about Jack Benny. So it was a great evening and I’m so proud of that experience.

Jack Paar:

Dave: I had a great deal of admiration for Jack Paar. And I started to spend more and more time with [him]. And I would get more and more comfortable with Jack Paar. And I began to notice that Jack, bless his heart, would tell the same stories over and over again. They were great stories, fantastic stories. But that was it. And then the inevitable, I think he started to dislike me.

Regis: Who? Jack Paar?

Dave: Yes. And then I felt uncomfortable. So I was always worried that if I relaxed and got comfortable with Johnny, the same thing might happen. Do you understand what I’m saying?

Regis: I understand exactly what you’re saying. I became friends with Jack Paar. I understand everything you’re saying. But he never spoke ill of you. He thought you were great.

Appearing on the Carson show for the first time as a comedian:

Dave: First-timers tend to do pretty well because in those days they had a wonderful screening system. They would have talent coordinators [who] would come to see you [performing in a club] and they would work out a set. They would say, Yeah, we think we like you and we’ll be back in six weeks. The last thing they wanted to do was have a guy come on and not do well, or a woman come on and not do well because this was “The Tonight Show,” this was the Cadillac . . . So you were pretty well-guaranteed through working with these people that you were going to do alright.

Making fun of presidents and his own political leanings:

Dave: I’ve been guilty of appearing to be playing partisan politics. However, I’d like to say for the record, I am a registered independent. You go where the material takes you.

Poor Bill Clinton. No president that I'm aware of got hammered harder than Bill - President Bill Clinton over the Monica Lewinsky situation. We beat up on him. We still use him as a reference. And then we were desperate. We thought, well, this was so easy. Then we got George Bush.

And within a matter of days, we realized our prayers had been answered. He's just as good in terms of material. It may appear to people that we have a slant one way or the other, but if a guy, you know, drops his dog or a guy straps his dog to the roof of his car, or if a guy gets a shoe thrown at him, well, this is where the material is going to be.

And so far, it looks like - in this race in particular, it looks like - and the same was true in the primaries with Hillary Clinton and Barack Obama. I think if you look back on that, we worked them over pretty good because they were going at it. Then you had this group. I mean, those early debates, I mean, who are these people? The Ringling Brothers? . . . I think that a case could be made, yes, that we are leaning one side to the other, but it's not driven out of anything more serious than who's easier to make fun of.

The Ed Sullivan Theater, the home of Letterman’s CBS “Late Show” since 1993:

Dave: We went in there and it was a minute or two away from being condemned, in actuality. And, by God, in a very short period of time they turned it from whatever it had been into just a first-rate television facility. And I’m from the school that you do TV in a studio. And so I was wondering if it could be, in fact, done from a theater. But the place is fantastic. I look around there every night and I think I’m so lucky to be a part of a production coming from this place because it’s both intimate and it’s as big as you need it to be and as intimate as you need it to be.

One subject Regis didn’t raise with Dave: Jay Leno.

You can watch clips of Dave and Regis here on And you can read a full transcript of the hour-long interview here.

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