Norm Macdonald is stuck on a golf course. “We have all these children in front of us, so we’re not going anywhere,” the 57-year-old comedian tells me by phone as he waits to move on to the next hole. “I watched the British Open and it made me think I could play golf,” he adds. “Turns out I can’t.”

It’s a Monday late afternoon and in just a few hours, the first new episode of his sporadic talk show Norm Macdonald Live is set to drop. He launched the podcast-turned-streaming video show back in 2013, but hasn’t put out a new episode in 10 months. This week’s guest is a big one: David Letterman. Their hour-long conversation reveals both Macdonald’s unconditional admiration for the retired talk-show host and Letterman’s enduring caustic wit.

It’s been a little more than two years since Macdonald got surprisingly emotional while performing his stand-up set on one of Letterman’s final Late Shows. “Mr. Letterman is not for the mawkish, and he has no truck for the sentimental,” Macdonald said eloquently at the end of his set. “If something is true, it is not sentimental. And I say in truth, I love you.”

Despite the hint of tears that night, Macdonald “has no truck for the sentimental” either. But two decades after he was fired by Saturday Night Live for making too many O.J. Simpson jokes from the “Weekend Update” desk, he does seem a bit wistful about the way things used to be in America. Before late-night hosts had to be “pundits” and gender wasn’t so fluid. The get-off-my-lawn attitude that he brought to his Bob Dole impression on SNL has started to seep into his real-life musings on the world. Still, he remains funny as hell.

It is important to remember, however, that everything that comes out of Norm Macdonald’s mouth must be taken with an enormous grain of salt. After all, he wrote a memoir this past year called Based on a True Story almost entirely made up of stories that never happened. He has a lot of strong opinions, but may not always be the most reliable narrator.

Just as our interview is ending, Macdonald shouts into the phone, “Oh, Jesus Christ! What are you doing?” After a short pause, he adds, “Oh my God, I just ran into a tree.” Asked if he’s OK, he replies, “Yeah, I’m fine.”

Below is an edited and condensed version of our conversation. [Note: This interview was conducted before President Trump issued his transgender military ban.]

So it’s been quite a while since you’ve put out an episode of Norm Macdonald Live. Why the long hiatus and why come back now?

Well, I was writing a book and it took longer than I thought it was going to take and I had to do a special. But mostly it was because I wasn’t interested in that many guests. And the guests I was interested in weren’t interested in doing it. I really wanted to get Robert Blake, but he kept thinking it was a joke. And I was like, oh no, it wouldn’t be a joke. I love that guy. And then I thought I had O.J. [Simpson] and his lawyer said, “Oh yeah, O.J. will do it.” And then he came back and said, “Are you the Norm Macdonald that was on NBC?” “Yeah.” And he’s like, “O.J. said you were a little tough.”

Yeah, I wanted to ask you about O.J. because there’s been a rumor for a long time that you were fired from SNL because you made too many O.J. jokes. So what do you think about the fact that he finally got parole this week?

I mean, I thought he was kind of burned on that thing the whole time. I was watching it and he didn’t seem to do anything very bad. It was just one of those things where everyone accepts that that lady judge [Jackie Glass] was trying him on a previous case that she thought he was guilty on without even having knowledge of the case. So I thought that was pretty bad. It seems like they do that all the time. If someone’s clearly insane and kills the president, they put him in jail instead of the crazy place. If he misses and doesn’t kill the president, like [John] Hinckley, then he goes to a mental place. So it seems very result-oriented.

What about all those O.J. jokes you made on “Weekend Update?” Do you feel OK about how that played out?

Well, I’m not completely sure he’s guilty anymore.

Oh yeah?

I’m almost completely sure, but I’m not completely sure.

What changed your mind?

The fact that his son may have done it, I guess. [This theory has been widely debunked.] They had the same DNA. I don’t know much about DNA. You know how O.J. was the greatest rusher in the history of the NFL? I guess I was the greatest rusher-to-judgment. Wait, one second, hold on. [The phone cuts out for a few seconds.] Sorry about that, I had to hit a tree.

But he provided you with a lot of material, so that must have been helpful.

Yeah, he was awesome. He was great. You know, I feel sorry for the victims of the double murder. Although I guess I was a victim also. I guess there were three victims that night. Nicole Simpson, some waiter, and me. Ron Goldman!

Ron Goldman, yeah.

You know what was funny? And it shouldn’t have been funny—but what are you going to do, you can’t stop your heart from laughing—was Ron Goldman’s father when he was on TV grieving, crying. Meanwhile he had the funniest mustache ever. So you were always torn about what to do. You wanted to laugh, because he looked like he was about to tie a lady onto some train tracks.

He still has that mustache, I think.

I saw O.J. on a golf course. And I was going to go up to him, but who was I with? Kato [Kaelin]. And Kato was afraid. Because Kato was, what do you call those guys? A reluctant witness? A hostile witness. Because what he did was, he was called by Marcia Clark and then he changed his testimony on the fly and caught Marcia Clark off-guard. I asked him, “Why’d you do that?” And he said that after he’d say something, Marcia Clark would kind of look mean, but Johnny Cochran would walk over to him and say, “You’re a funny man, Kato Kaelin, you’re a very funny man.” [imitating Cochran’s voice] So Kato loved being “funny,” in quotation marks. So he got seduced by the great Johnny Cochran.

Well, maybe O.J. will come on your show now once he’s out.

I think he will. I know his lawyer, so his lawyer like guaranteed me that he’d be on. And then O.J. went against it. But yeah, maybe now that I’m making such an impassioned defense of him, saying I’ve changed my mind, yeah.

So I also want to talk to you about David Letterman, who’s the first guest on the new season of your interview show. The last time we saw the two of you together was your emotional final stand-up set on The Late Show. Why did you want to turn the tables and ask him questions?

Well, he was a guy I really wanted. You know, it’s funny, when you get to interview people—well, you know this—almost no one is interesting. You have to really think up questions, because everyone’s so deadly dull, you know? Especially in show business. So there’s really nothing to say unless you take it as seriously as they do. And then you look kind of foolish. It did make me realize how great Letterman was, because, I mean, he had more contempt for show business than I do and somehow he could do it. He could interview these vapid actors. It was incredible how he could do both the satire of the show, but also the show itself. It was very impressive.

It’s kind of like he had to do the interviews in order to do the comedy, like a trade-off?

Yeah, I guess he probably would have loved to have no guests, I would imagine. Just from talking to the writers on the show, he would always stress that it was a comedy show, not a talk show—a comedy show with guests.

Are you envious at all of the way he has more or less walked away from show business?

Oh yeah, that’d be awesome. That’s the greatest. I mean, he’s not like [Johnny] Carson. He sprouts up once and awhile. Carson was so afraid to look like Bob Hope and Letterman doesn’t want to end up like Carson. But yeah, I would love to exit show business forever. That would be the greatest thing ever.

On the flip side, you lobbied to replace Craig Ferguson on The Late Late Show a few years ago. I don’t know how serious you were about it—

I was kind of half-serious.

Do you still have aspirations for a gig like that one?

Nah, it would be way too hard. Really, I was always puzzled that I never got to guest host ever, any of these shows. That’s what made me say that, because I was watching one of the guest hosts for Craig Ferguson and one of my buddies was a writer on the show. And I was like, what? He got it before me? And then they asked [CBS president] Les Moonves, and Les Moonves said he didn’t know who I was. That’s a play they make, where they go, “Norm who?” Meanwhile I’ve been to the guy’s house like three times. But that’s just this cool, little power play that they make.

They ended up going a pretty different direction with James Corden.

Yeah. Look, they were right, you know? They were right. I was talking to James Corden and he said, you know, “Jimmy Fallon is the gold standard [for late-night hosts] and that’s what I’m going to try to do,” and that’s what he did. And that viral stuff is all that matters. When I was growing up, it was always Letterman. I didn’t really know Carson, because he was kind of corny by the time I watched. But I took it on faith that he was good, you know, because Letterman said he was. But the interview part was like—Chuck Woolery’s on tonight. It didn’t matter who the guest was, it was, how is Letterman going to interview Chuck Woolery? That was the funny part. But you could do the greatest interview ever, it would never go viral.

Right.

It’s funny, because when I was a kid, they had those kinds of shows, like Party Game. This was in Canada. It’d be like B-level celebrities playing charades. And now it’s returned, all these games. But not good games. Just kind of having fun. Watching people have fun never appealed to me that much. It always just highlighted how little fun I was having watching them.

You were on Fallon’s show the same night that he mussed Donald Trump’s hair. When you saw that happen, did you realize how big of a problem it would become for Fallon?

No, I didn’t. There was a whole bunch of people watching it [backstage] and everybody was laughing and thought it was cute. So I was very surprised by the pushback or blowback or whatever that new word is. But Fallon, he’s never going to host Meet The Press. He just does what he does. He has fun. He likes to have fun and laugh. Also, I don’t how you blame Fallon when every media outlet in the world had Trump on and treated him with kid gloves until it was too late. But I thought it was absurd. I really hate—I’m so bored with politics. So I just watch sports. You know, they show the old Carson shows and he never mentioned—during Watergate, he’s doing these really tame, little jokes. I wonder when it happened. Maybe with Jon Stewart. But it happened at some point that talk show hosts had to be political pundits. And if a train explodes outside of my house, I have to have James Corden talk me through it. The funny thing is, they cry and they talk you through it, and then after the commercial, they’re like, “We’re back!”

Time to play a game.

[Laughs] Let’s play a game! And we’ll try to get through this show, and we’ll do what we can, but after a break, “We’re back!”

Did you watch Saturday Night Live this past season?

Oh yeah, yeah. Oh my god, did you see that? And this wasn’t even a tragedy; just a guy got elected. They open the show with Kate McKinnon singing “Hallelujah” by Leonard Cohen. And I was sad Leonard Cohen died, I love Leonard Cohen. But at the end, Kate McKinnon said, “I’m going to get through this and so are you. [The actual quote was, “I’m not giving up, and neither should you.”] I was like, what the fuck are we getting through? That a man was duly elected president? What are you, crazy? Like, at first, I seriously thought she meant Leonard Cohen’s death. And I was like, well I can get through that. I can get through anything. I got through my own father’s death. You think I can’t get through a man getting elected president of the United States? It was so absurd that, for some reason, she was the one that was supposed to let me know that it’s alright to go on. Go on as if nothing happened. Nothing exploded.

How do you think the show has done with Trump in office, with Alec Baldwin and Melissa McCarthy and all the guests they brought in?

I love Alec Baldwin. And one of my best friends, Jim Downey, writes the political sketches. Or used to. [Downey came out of retirement to write for SNL again in the fall of 2016.] And they were great. But they were always funny. I don’t know. I have different ideas on that than most. But I think they’re playing into Trump’s hands. Because if you satirize someone, or mock them, you’re trivializing any danger that they might be. I don’t know any other way to do something. You can’t get a laugh without making the person more likable. Plus, I don’t think comedy does anything anyway. I was reading this book—I’m kind of obsessed with Hitler, you know? And they were saying, when Hitler took power, all these comedians and sketch troupes would do Hitler. They’d put a comb under their nose. They all hated Hitler and they’d make fun of him. Hitler didn’t care and then he did all those bad things. I don’t want to get into the details, but this guy was no saint. So I have no historical precedent that comedy ever changed anything.

So if you were still doing “Weekend Update” on that show now, what would your approach be?

I don’t know. I always wrote non-political jokes, because I just hate politics so much. Jim Downey wrote the political jokes. And I was kind of shocked, because someone sent me a thing of all the Hillary [Clinton] jokes I did. It was like 20 minutes of them. And they were all, everyone of them, the premise was that she was a huge liar. And that was like 20 years ago. I didn’t know that. I guess she was. My theory is this: People hated Hillary Clinton so much that they voted for someone they hated more than Hillary Clinton in order to rub it in. And if you think about it, this is also the only presidential election we’ve had where only one guy ran.

Where there was only one man in the race?

Yeah, just one guy. Usually they have two guys, or maybe three. This time, one. You know, it’s funny how you think you have choice. Because whenever people talk about dictatorships and they go like, [Vladimir] Putin got 100% of the vote or Saddam [Hussein] got 100% of the vote, it’s like, yeah, because one guy ran. And then we’re like, we could never understand one person running, it’s beyond our comprehension. We have two! Just the addition of the extra one, suddenly we have choice. It’s so absurd. And I never like a political candidate. I find it very hard to vote for someone who’s going to have power over me. It’s such an odd thing to do, to go, yeah, this guy should control my life instead of this guy or this lady. I know it’s stylish now to have ladies running.

So there have been no U.S. presidents in your lifetime that you’ve liked?

Well, I don’t know anything about politics, so I just like the charming ones. I liked Clinton and I liked Reagan. I remember I did the press dinner, or whatever they call it, where you do jokes in front of the president [the 1997 White House Correspondents’ Dinner]. And it was Bill Clinton and he comes in and he talks to everyone, you know? He came in with a big, red, happy face, looked like a drunk, stoned guy. And she comes in, Hillary, and is just sour. But he goes to every person in that room, there were about 200 people. So I was like, I wonder what he’s going to say to me, because he’s got to say something different to every person. So I was just standing there and you know, when you meet someone that powerful, you kind of go into a fugue-like state that you don’t remember until later. But he came up to me—I had a sandwich, I was eating a pickle—he shook my hand and said, all charming and everything, “I see you’re eating a pickle.” I was like, “Yes.” And then he kept moving and I’m all happy and beaming. And it wasn’t until that night when someone said, “What did the president say to you?” And I said, “Actually, he asked me if I was eating a pickle.” Or he stated categorically that I was eating a pickle. And I found it to be very, very charming.

That was all he could think of to say at that moment, I guess.

Yeah, I mean, what the fuck are you going to say? You just look at the person and go, “Oh, I see your shirt is blue” and move on.

I want to talk about another guest you have coming up on the show, Caitlyn Jenner. I know you’ve made some jokes about her in the past and recently she was on Jimmy Kimmel’s show and he actually apologized to her for some of the jokes he made. Did you apologize to her?

No, no, no.

Or do you think that comedians owe her an apology for making jokes during her transition?

No, you know, I do worry sometimes about doing any joke and then some guy will then kill a transgender person because you did a joke. You always have that concern. But you can just do a joke about being confused about the transgender thing. And that’s the thing that I find funny, is that everyone just understands it completely, in a day. And I’m like, c’mon, man. I’m like this old man, give me a week at least to try to figure this out. My jokes all came from confusion. The one question I had [for Jenner] is, what’s a woman? She couldn’t answer it. That’s what I find most confusing about it. It’s a woman trapped inside a man’s body. Then, what’s a woman? And he had no answer. Or she, rather. You get in trouble for pronouns. She had no answer for what a woman was because women like to pretend that women and men are the exact same. But then if they are, they can’t say they are women trapped inside man’s bodies. But he’s very, or she I should say—it’s a she if you look her in the face and it’s a he when you’re shaking her giant hand. There’s nothing you can do with your hands, I realized talking to her. They haven’t come up with that yet. But she was very charming, and she’s going to golf with me. She’s a scratch golfer, for God’s sakes. She hits the par fives in two. And I said, “You go on the ladies tees now?” And she said, “Oh yeah.” And I thought that’s a bit unfair.

Anyone else coming up that you’re going to interview that you’re particularly excited about?

Jim Carrey. I’m excited about Jim Carrey, because he’s from Canada and he’s just always funny. He’s just a “has-to-be-funny” kind of guy. And I really want to get Robert Blake. I’ve been trying to get him since the first show and my stupid producer, he was trying to talk him into it, and he went, “Look, I can’t talk now, I’ve got to go to dinner with my wife.” And Robert Blake got all mad, like he took it personally. But I want to get him and I want to get O.J. real bad. But we have really good guests. Tom Hanks. I forget all the people’s names.

[At this point, Macdonald’s publicist comes on the call to tell us time is up.]

Well, I’m sorry I went off-topic.

No, there’s no such thing as off-topic.

Well, that’s true. Plus, feel free to write anything. I’ll say I said it.