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. Right, right. 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.

What about Lorne Michaels? He’d be great. I like Lorne a lot and I think the most interesting thing to me about Lorne (or about anybody), is how funny they are. Lorne is really, really funny. They never mention that when they talk about Lorne because he’s a powerful guy with money and control and success and everything, so they always go with that, but he’s really funny. I don’t care about that. I’ve met rich people, you know? He’s very funny to talk to and people don’t see that because I guess he gets serious in interviews because they’re very serious questions, which is kind of odd to ask of a person whose whole life has been comedy, you know? They don’t do it with anyone else, but they do it with him.

There’s so much social importance on SNL now, especially with the amount of politics that they talk about. I think that’s part of it. Yes. Yes. But knowing his background, it’s not surprising that he’s a funny guy. You know, Lorne… I will say, though, because I hate politics, you know? I remember when I went there I go, “Lorne, I don’t want to do political jokes on Update.” You know, because Update is about the news. Then he’s like, “No, no. As long as it’s funny. It doesn’t matter to me.” So Lorne’s not really political. He just chooses his opinions the way most people do, just the way you choose a tie, just whatever’s stylish at the time. You know? Yes. The only interesting guys are guys that think differently than every other single person. You know what I mean? If I was to interview anyone with a political spot, it would have to be someone that was way outside the mainstream. Or maybe not outside the mainstream. You could be in the majority. You could be a Trump supporter and be considered fringe in the media. You know? You could believe in abortion and be considered a lunatic, even though the majority of Americans vote against it. I’m sorry [I mean], you could be against abortion. All that kind of stuff just depresses me and I find it dull. I never found important stuff to be that funny. It just makes the comic look as self-important as the figure that he’s lampooning. Like the way that James Corden has to talk us through the Manchester attack or something. You know, it’s kind of insulting. I can imagine that it’s hard when you do a joke that’s based in politics where you have to cut off half the possible audience.

Oh yeah, yeah. You know, Leno uses that. He goes, whenever a guy is on stage, he goes, “Oh, he just lost them,” because Leno just looked at it as truly just getting everyone to laugh, which became out of style at some point, but those are the comedians that I like. I think they’re more important, in a way. Someone like Jerry Seinfeld, who can talk about very, very tiny things, like cereal. You know? And people make fun of him for that, but that’s much more a part of your life than Donald Trump. Donald Trump, you might think he’s gonna affect your life, but he’s not really gonna affect your life. At least, I don’t think so. To me, it varies. Depends on your life, where you’re at, and what you’re in the middle of. I can see it both ways. Yeah, but I mean there are some things, for instance: abortion. It’s been decided. It’s not gonna change. Even healthcare, it’s not gonna change. Americans are going to expect healthcare as their right, so it doesn’t matter what the Congress says or what the President says or anything. Or gay rights, you know? None of this was ever decided by a politician. It was always decided by the hoi-polloi, you know? We decide things for ourselves more than we think we do. We’re certainly not living in a dictatorship as it’s imagined by some people. And I think it’s imagined that way because, like you were saying earlier, since it’s not gonna change my life, I have to pretend it’s gonna change all these other people’s lives that are beneath me, you know? But I don’t believe that. I think politicians are just like entertainers. In the United States, I’m talking about. Because we’re given so much freedom that there’s this gridlock. We, on purpose, usually vote the executive and the Congress against each other so the gridlock will continue and now even with an all Republican Senate, the constituents won’t allow anything but gridlock. But I understand that. Nobody wants to change.

Just to go back to the show… Because you don’t like politics, I’m sure you don’t want the whole interview to be about politics. I know, I hate politics and now I’m talking about it. [Laughs] Yeah. Are you happy where you are with the show on YouTube where I imagine you have creative freedom? Moreso than you would be if you were on a network?

Oh yeah. I would never want to be on a network. If it was Netflix or some place that allowed total freedom, yeah, but a network, of course, would never allow that. So I’m much happier. Not only am I much happier, but I couldn’t do it on a network. They would just fire me instantly. I’m happier and they’re happier that I’m not there. And also, with the politics. Every talk show host is a political pundit, and it drives me crazy because I like watching. I used to like watching talk shows. I watch Fallon now because he plays games and stuff, but I like Letterman because he was above politics and Carson and things like that. That’s another reason, I don’t know who started… maybe Jon Stewart, but Jon Stewart was a singular talent. And I know I’m talking about politics again [laughs] but I think we’ve come to some weird point in our culture where we want our clowns to talk us through tragedies. It’s sort of silly. I like just complete anarchy. That’s my favorite thing. We’ve done a couple shows, one with Super Dave and one with Larry King where it just went crazy and it was like… That’s the funnest. They have to go along with things because that’s what people do. I watched your Bill Hader interview. He is so funny! That was the best one just because he’s such a funny guy and also so lovable. Do you guys know each other or was that chemistry just there on the spot? I never met him before. I never met him. Wait, actually, I did. I met him one time because he was in a hotel and he was writing on South Park. But no, I don’t think I ever met him other than that, but he’s just such a sweet, sweet guy. You’re part of that SNL fraternity. When you speak to somebody from SNL, do you think it’s easier to get them to open up about the show because you share that relationship?