• by Adam Buckman , Featured Columnist, May 11, 2015

Only eight shows remain for David Letterman until he leaves late-night TV after an extraordinary run of 33 years. How's he feeling about the approach of his final show May 20? I asked comedian Tom Dreesen, Dave's close friend of more than 40 years, and one of the nation’s top stand-up comedians. Dreesen was Frank Sinatra's opening act for 13 years, and the two became close friends -- a relationship that formed the basis for the live show Dreesen performs around the country, “An Evening of Laughter and Memories of Sinatra.”

Dreesen appeared on Letterman's late-night shows on NBC and CBS more than 50 times. In a phone interview last week, Dreesen, who made his final appearance on Letterman's “Late Show” on April 14, talked about his friend and speculated on what Letterman, 68, will do next.

TV News Daily: How do you think it will be for Dave to leave his nightly TV show?

Dreesen: It's going to be very, very difficult for him, because when you're on a show that long, how do you just stop cold one day? All those people on those shows that meant [so much to him]. He meets with the writers after every show and they become like your family and it’s pretty hard.  … Look, I spent four years in the military, I can't tell you how hard it was for me to transition from the military to civilian life. I can't imagine doing [a TV show for] 33 years …  And by the way, there's a similarity between having your own show and the military because you're time-regimented. It's a routine everyday and you become comfortable with it. And you get caught up in that routine and … I know how hard it is and I'm sure he's given it a great deal of thought.

TVND: Will he be okay?

TD:  Yeah. And I don't know that I would have said that before [the birth of Letterman's son] Harry [now 11]. But yes, because of his love for Harry and Regina, his wife – that's going to keep him grounded. He'll be okay. 

TVND: Unlike Dreesen and other veteran comics such as Jerry Seinfeld and Jay Leno, Letterman has never cultivated a live, stand-up career in addition to appearing on television. So I asked Dreesen: We shouldn't expect to see Dave turning up in nightclubs and casinos, should we?

TD: If you would have, he'd have been doing it all along. Do you know how much money he's been offered to go to Vegas, go to Atlantic City? He used to say to me, ‘What would I do?’ And I would say, ‘Are you crazy? Do stand-up. Take Paul [Shaffer] with you. Paul could open the show, do some stuff and then you'd come out. He’d introduce you. You'd do your stand-up, you could bring a couple of novelty acts with you …’ But Dave never loved stand-up. He was good at it, but he didn't love it. 

TVND: If he was never quite comfortable doing live stand-up comedy, Dreesen says Letterman was born to perform in a TV studio. Dreesen remembers:

TD: I saw him when he first went on-stage. This raw kid from Indianapolis who really came [to L.A.] to be a writer. He had a quick mind and yet, he was never comfortable, to me, on the nightclub stage. But he was funny. Then one day I went over to see him on a television sound stage. When I saw him walk out on that first ‘Tonight Show,’ I said, ‘Oh my God, he’s home.’

TVND: Dreesen also accompanied Dave when Letterman guest-hosted for Johnny Carson on “The Tonight Show” for the first time.

TD:  I’ll tell you another great story that no one knows. I went with him the first time he hosted ‘The Tonight Show.’ I was standing in the wings watching Dave ready to come out and I felt this presence behind me and I turned around. It was Tom Snyder. He [hosted NBC’s “Tomorrow” show] that followed Carson, and I turned around and Snyder says, ‘I want to see how the crowd reacts when this no-name comes out.’ And one year later, David Letterman replaced Tom Snyder. I never told Dave that story.

Watch Tom Dreesen with his friend David Letterman on their final show together April 14 here and here.