The fearless Canadian comedian, who died this week at 61, reflected on the laughs that he made (and the ones that made him) in a 2018 interview.

Norm Macdonald was a standout standup who delivered surprising jokes at his own off-kilter pace, from his own ZIP code. He was fearless and withering, folksy and matter-of-fact, and he could score at will with his commitment to the bit, and sometimes you had to wait a bit. As Weekend Update anchor on Saturday Night Live, the former Roseanne writer gave many inappropriate laughs and precisely zero f‑‑‑s. Not to mention, he could deliver bad jokes perhaps better than anyone. The comedy world was devastated by the news on Tuesday that Macdonald had died at the age of 61 after a private battle with cancer.

In 2018, EW interviewed Macdonald as part of our Comedy of My Life franchise as he prepared to launch the Netflix experiential talk show Norm Macdonald Has a Show (which was based on his video podcast Norm Macdonald Live and executive-produced by one of his heroes and biggest fans, David Letterman). Here's how Macdonald described what to expect from the interviews on this show: "The conversation has no beginning, it has no end, there's nothing I want to get to, there's no important questions." But as audiences over the years came to learn, a nebulous journey with Norm always ended in laughter. Below is the extended version of that Comedy of My Life article, in which he looked back at the comedians who shaped his sensibilities, the strange venues he toiled in on his rise to fame, the bits that he was proudest of, and the joke that he wanted on his tombstone.

The first joke I told

In school, they were talking about probability [when] flipping a coin — 50 percent heads, 50 percent tails. One kid said, "Wait, what if it landed on its edge?" And the teacher said, "A coin could never land on its edge." And I said, "What if you were standing in mud?" I got a huge laugh. It was grade 2. I remember it very, very vividly.

Norm Macdonald
Norm Macdonald
| Credit: Gary Miller/Getty Images

The standup special that made me want to become a comedian

Richard Pryor's Live on the Sunset Strip, and particularly the bit about him trying to get [a stripper] paid by the owner of the club, who is a mob guy. It informed my comedy probably more than anything. He said, "I'm gonna go in. I'll do my scariest s‑‑‑ on this guy." So he came in with a gun, and he says to the club owner, "You're gonna pay her." And the club owner starts laughing… The terrifying part of this guy was that he was laughing, that it was beyond his comprehension that this couldn't be a joke, that no one would ever pull a gun on this guy. And I learned from that that my funniest bits are when it's a reaction that's wrong, but truer underneath than what you would expect. And it made me realize: Think of a different reaction to what you should have. Think of a different way to say this than people would expect. In fact, think of the opposite way.

The joke(s) I regret telling

I guess the jokes that I really hated in retrospect were just the fact that I liked them at that point. Because I liked the joke at the time I did it on stage, that's what makes me so ashamed. It's not the joke itself, but it's a combination of the joke and the fact that I was proud of that joke. I remember this joke I used to do that I thought was not only funny, but provocative — and it's just f‑‑‑ing awful. It's [about] abortion. "There's two sides: There's people that are pro-choice, and then there are people that are pro-life. I'm not really either one. I just mean people should be careful, should practice safe sex. I guess you can call me pro-phylactic." I thought I was really breaking ceilings with that joke.

The best heckle I've received at one of my shows

The heckle that stops you dead is when they say, "Next." It's so jarring and unanswerable. It's such a brilliant heckle, so that's the one that frightens me the most when I hear that. No comeback. There's absolutely nothing you can say to that, except "No."

The weirdest place I've ever done standup

I'll try to make this short. I had only been doing standup for a few months. It was me and another guy, and they said, "We got a gig for you. It pays $25 each." It was New Year's Eve, which was the very prestigious time to get a gig. It was at the Chateau Laurier, which was a very famous hotel in Ottawa — our most regal of hotels. And we were going to play in the McLaughlin Room at the Chateau Laurier. So me and the other comic get there. There is no McLaughlin Room. We keep asking. Turns out it's just a hotel room, booked under a guy named McLaughlin, you know? So now, we're completely freaked out. We were all confident before. So me and the guy go to the room. The guy says…

Okay, I'm gonna tell you another one. It's not as bad, but it might be funnier. I was doing a corporate gig, and corporate gigs are terrible. And they often have an idea for you to do. It was a pesticide company, so this guy had sent me hundreds of pamphlets on pesticides. And at the time I had 10 minutes of material that I could not veer from, and I have no ability to go off script for this 10 minutes about telephone answering machines or whatever the f‑‑‑ it was. So the guy says, "There's a new guy that's been hired in New York, the head of publicity. The new guy is a wunderkind. No one's met him! We'll pretend that's you!" So I'm like, "Great." So he says, "Let's go in." So he goes, "Do you want anything to eat?" I go, "That would be nice." He takes to me the front table, so now I'm with the head with all these bigwigs in the pesticides group, and he's introducing me to these guys as this wunderkind from New York, the head of their PR. They're all interested me, and I'm eating, trying to ignore their questions. So then he introduces to me this 5,000 people. He's like, "Here he is, the guy you've been waiting for, we've all been talking about — Andy Johnson!" The place goes insane. Because they've heard so much about this kid, Andy Johnson, but they've never seen him or met him. And then it's me. I'm Andy Johnson. I go up. I do my answering machine jokes and so forth. Zero response. It goes on for six, seven minutes. Nothing. Finally, I hear a guy yell, "Enough with the jokes!" [Laughs] Which is perfectly reasonable for him to say. And I go, "Ohhh." And I stutter. Then the guy that set up this joke, he runs up the side and he goes, "Folks, this is a joke! This isn't Andy, the guy you all wanted to see! This is Norm Macdonald! He's a comedian!" And then he runs away. And then they hate my guts, you know? They just boo me all the way through.

Okay, that's that story. I'll tell you the other story, in case it's better. So we go to the McLaughlin Room. It's me and the other guy, and now we're freaked out because we thought we were going do a big room in the Chateau Laurier, instead we're doing an actual hotel room. No one's in the room. A guy comes in. He's McLaughlin. It's his room. For New Year's Eve, he was bringing his friends all around the city on a magical mystery tour. So he'd go here, and then there, and then here, and then there. And one of the stops was this stop. As a matter of fact, it was the last stop. They had the place set up — this suite — with food and so forth. So he said, "We're gonna bring in about 30 people, then you entertain them." So we go, "Okay." So he goes, "They'll be here in like five minutes. Hide!" So we're like, "What?" He says, "Hide!" Then he leaves, and then we're all alone in this f‑‑‑ing hotel room. So my buddy gets behind the curtains, like in a movie, where you see the feet, you know? He's behind the curtains. He's going be the emcee. And then I'm going to go on last. So I lock myself in the bathroom and turn the light off. Now I'm in complete darkness, and I hear people entering the room. I hear small talk, I hear food. And then I hear people trying to get into the f‑‑‑ing bathroom, and I'm just cowering. Then I hear my friend, and I guess he just leaped out from behind the curtains. He gives me the introduction. I'll never forget it because it's an introduction that only makes sense at a comedy club. I get out of the bathroom from being in blackness for 15 minutes into something that looked like Eyes Wide Shut or something. They all had cock noses on, which I guess was from a different part of their magical mystery tour. Plus, six people want to get in the bathroom, so they were really angry at me and pushing me aside. So I run in the middle of them, and they're all surrounding me. I'm like, "What about those answering machines?" A girl puts a cock nose on my face. Now I have a cock nose. And then she hits me on the head with her hat, and then that gets a big laugh, so then everyone starts hitting me on the head with their hats. And then I look over, and my friend has left. He's run away. So that one's the worst. That was my New Year's Eve.

The Weekend Update joke I'm proudest of

I like this joke because it was perfect. It was a joke you couldn't do anywhere else, and the joke was: Jerry Rubin had died that very day. And he was a yippie. He was famous as a yippie. So the joke was, "Yippee! Jerry Rubin is dead. I'm sorry, that should read: Yippie Jerry Reuben is dead." I like that one because the punchline and the setup were exactly the same, and it only made sense as a newsman to do that joke.

The O.J. Simpson joke I'm proudest of

The one that I always remember — and Jimmy Downey wrote it, I didn't — was when they showed [Simpson's] hat in court, and that it didn't help O.J.'s case that much when he jumped up and said, "Hey, hey! That's my lucky stabbing hat!" The idea of a lucky stabbing hat makes me laugh.

Saturday Night Live - Season 20
Norm Madonald on 'Saturday Night Live'
| Credit: Al Levine/NBC/NBCU Photo Bank via Getty Images

The talk show host who could save any situation

Johnny Carson. The reason he's so brilliant is because you can't be funny five days a week, 60 minutes a day. It's just not possible, you know? So he could be not funny and make it funny. He had two ways to be funny: to be funny, or to not be funny. He had it covered completely, in every way. I've seen other people try it, but I've never seen anybody succeed at it except for him.

The late-night talk show host who influenced me the most

As far as wit goes, Letterman is without peer, the fastest. That's what I love about Dave. Many times, if you watch Dave, he'll have a joke. He's ready to say the joke. The guest interrupts him and continues on, Letterman stops and doesn't go back to the joke. He bails on that joke instead of interrupting the guest, because he has the confidence to know that he'll be able to come up with a joke later. And he also doesn't return to that joke, because I've seen people do that. "Yeah, earlier when you said that" — he never did that. And I've seen him swallow jokes so many times that it's very, very impressive.

David Letterman understood that to subvert something, you first had to master it. He knew everything about talk shows. He had obviously studied them assiduously. So if you watch, there's probably 80 percent extremely standard talk show, as standard as you can make it. Twenty percent destroying the other 80 percent.

The best advice David Letterman ever gave me 

He told me not to prepare. This was advice that he didn't give as a universal, but he was just saying that this would be good for me personally. I've known Dave for a long time. He said, "Norm, you're much, much better if you don't know than if you do know — because you're curious and you're kind of an idiot. And the things that you think of instantly, when the person's explaining it." Because when I'm having dinner with him or something, I'll just have some question a 2-year-old would ask that everyone else knows and stuff, and I don't. So that was his thing, was, "Don't prepare. Just interview Elon Musk blind and see what happens." It was funny, because I had overprepared for an interview, and he noticed that. He said, "Did you prepare a lot for that interview?" I went, "Oh yeah." He goes, "Don't do that."

The question I ask my guests just because it amuses me

I love asking my guests to "tell the folks at home…" The guy will say, "We were at dress rehearsal…" "Okay, now explain to the folks at home what a dress rehearsal is." It makes them have to look at the camera and say, "Well, this is…" Later they'll go, "I was in the backyard with a shovel…" and I'll go, "Okay, explain to the folks at home what a shovel is." "Why do I have to?" "Just do it!"

The funniest word to say on stage

The two-word phrase I use most of all is "cheese sandwich." But I guess the one word would be "hat."

The joke that should be told at my funeral

I might put this on my tombstone: Roses are gray, violets are gray, tulips are gray, because I am a dog.

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