Few comedians have earned the sincere reverence that Norm Macdonald has, but David Letterman qualifies, and in the season premiere of Macdonald’s YouTube talk show on JASH (which you can subscribe to here), the two shared a soundstage for the first time since Macdonald’s teary farewell performance near the end of Letterman’s Late Night run in 2015.
In the interview (which you can watch in full down below), Macdonald and Letterman trade compliments and discuss Letterman’s early career in stand up and his late night run. It’s catnip for comedy nerds, but it also presented a challenge and a bit of uncomfortableness for Macdonald, as he tells us in our own interview, which touches on Letterman, people’s persistent fascination with SNL, politics in late night, and the lost art of late night long form interviews. This all over the phone while he was caddying as penance for an awful golf game.
Norm Macdonald: Sorry, is this Pete? P-E-T-E?
Uproxx: Jason. J-A-S-O-N.
Oh Jason! I’m sorry. I don’t know, you could have spelled it P-E-T-E, you spell Uproxx all wrong. How’s it going?
Good. How are you?
I’m alright. I’m alright. I was golfing, but now I’m caddying for this guy.
How’d you do?
So bad. Now I’m caddying! This is what I do: I watch the British Open and then I think I can golf. I watch NBA and then I think I can play basketball. But it doesn’t work that way. If you don’t put the work in, you know?
So, Letterman, you get him on the season premiere of Norm Macdonald Live and he says some really wonderful things about you. How do you process that when that’s going on? How does that feel?
Yeah, no I don’t like that. I mean, it was very nice of him. I know what he was intending by it and it was very sweet of him, but, oh God, no I don’t like that at all. That can never be funny.
You looked a little uncomfortable.
Yeah, I was uncomfortable, because you’re always looking for the joke part but as soon as that happens, there’s no joke anymore. All of a sudden, it’s something different. It was very, very nice of him to say, but… When you’re a comedian, it’s not supposed to be pointed out that you’re a comedian. It’s like if someone said, “Hey, David Copperfield. You know what I like? When you bought that trick at that magic store shop.” I don’t know. That’s not really like that. I was just stretching.
What’s the best part when you’re conducting an interview? What is it that you’re looking for when you’re doing one of these?
It depends on each person. Letterman was really hard because I was so afraid of him, but normally it’s easy to do. Luckily, I’ve gotten to just interview people that I like. I realize after I’ve done a little bit of this interviewing nonsense that just to interview anyone is incredibly hard. Like Letterman, who had much more contempt for show business than I do, was able to interview vapid actresses, each after another, and found a way to do it. It made me realize that I don’t know how to interview. I only can interview people that I’m interested in. Then the questions are easy, you know?
Do you use that fear to your advantage when you’re trying to figure out what to ask?
No, I don’t do anything. When I had Larry King on, he was like, “don’t know anything about the person.” Maybe he’s just lazy. I don’t know. It’s hard, like reading all this stuff with these people and going on Wikipedia and then realizing how uninteresting they are. It’s better to just talk to them like a human being and hope that something happens.
I’ve read that. You don’t want to have too much research, too many notions of who they are or what they’ll say.
Works to your advantage.
I think one of the reasons why I even did it is I loved Tom Snyder and I loved Dick Cavett and those guys that did real long-form interviews. They were much different then. I’m not sure I could do a short-form interview because then you have to get to the point so quickly and usually it’s just plugging a book or something anyway. If you’re given an hour or an hour and a half… One time we did a three-hour interview. But eventually, they’ll say something, like their guard will be down and they’ll forget they’re on TV.
It’s like the greatest interviewers are policemen, you know? Because they put you in a room and then they leave and then they come back and they offer you a piece of pie. And then they keep talking and talking and they go, “Come on. We know what happened,” and you’re like, “You do?!” Then they’re like, “Yeah.” Part of your brain is like, “There’s no way they could know,” but the other part of your brain is like, “Goddamn. I could use a piece of pie.” By the end of the thing, you’re so broken emotionally that you confess to a crime that you never even committed just for pie! I don’t mean to get too worked up about it, but those guys are the greatest. Those are the guys that should have talk shows.
I think if you look now, the guys that are the best interviewers in the business, guys like Howard Stern, it’s that same kind of thing where he just kind of grills you for an hour and eventually, you see people kind of spill. Like you’re saying.
Yeah. Howard Stern, he’s brilliant. Whenever I’m on his show, I go, “How do you do this?” He does a lot of cool things when he’s interviewing you. First of all, he listens. Like if you say something, if you say, “Anyways,” and you say someone’s name, then he goes, “Oh wait, you don’t like her?” or “You don’t like that guy?” And somehow he catches it just by the way you say it because he’s listening. But the other thing he does is he agrees with whatever you say. If you say, “Oh man. The tough thing about doing movies is the directors.” Then he’ll go, “I did a movie. I hate directors. They’re idiots, most of them? Right?” Then you’re like, “Yeah. Right.” You want to agree with him, he’s agreeing with you and then suddenly you’re saying all this bad stuff, which he’s only saying hypothetically. So he’s the most skilled interviewer by far.
Is he someone you’d want to have on the show?
Yeah. He’d be great. It’d be amazing.