"Macdonald was not only one of the funniest comics of his generation, but also a sneaky aesthete who elevated stand-up, helping shift its cultural prestige over the past few decades into an art deserving respect," says Jason Zinoman of the late comedian and "Weekend Update" anchor, who died Tuesday at age 61. "His legacy is not clear from his level of stardom or even his list of television shows and specials, although he has some signal accomplishments, including an early stint as a writer on Roseanne and one of the best Netflix specials of the past decade, Hitler’s Dog, Gossip & Trickery. Macdonald’s greatness is not on his IMDb page so much as in the number of you-have-to-see-this moments, the kind that friends tell you about at parties and then send you the clip the next day. Many of these came from talk shows, where he was a hall-of-fame guest. He told one of the most justly revered jokes in late-night history on Conan O’Brien’s Tonight Show, a preposterous masterpiece of literary suspense-building about a moth in a podiatrist’s office. Another moment on the couch from the same show went viral decades later: He interrupted an interview with the actress Courtney Thorne-Smith to savagely insult Carrot Top, the star of the movie she was promoting, a brutally hilarious act of sabotage. Macdonald had other talents. When it comes to parodies of roasts, he stood alone, turning intentionally awful jokes at the roast of Bob Saget into disorienting performance art that remains one of the funniest bits of anti-comedy you will ever see. And on Saturday Night Live, he may have been at his best on the 'Weekend Update' desk (ultimately getting fired after his jokes about O.J. Simpson), but he also delivered several singular impressions, including a version of David Letterman that was both accurate and far too bizarre to be realistic. Letterman proved to be a key figure in Macdonald’s career, a champion of the stand-up’s work (the talk-show host said no one was funnier) who booked the comic on his show’s final week. Macdonald, breaking from his trademark acerbic style, ended on a surprisingly moving tribute, displaying an emotional side that usually only lurked under the surface of his comedy. In a column from 2017, I argued that what distinguished Macdonald’s comedy was his sensitivity to language, his peculiarly poetic brand of plain talk. He made stylish turns of phrase and folksy flourishes seem conversational and offhand. A lover of Bob Dylan, Macdonald was also a sponge for influences, borrowing and repurposing figures of speech or unusual words to create funny-sounding sentences. But describing him as merely a master of joke writing misses his quickness, wryly deadpan delivery and, most of all, a unique level of commitment. He did not bail out of jokes and never pandered."
Courteney Thorne-Smith loved Norm Macdonald roasting her on Late Night with Conan O'Brien: Thorne-Smith's May 1997 appearance with Conan promoting her and Carrot Top's movie Chairman of the Board made the rounds on social media following Macdonald's death. Vanity Fair contacted Thorne-Smith. "A few people have reached out. Everyone is so shocked," she says. "He’s always been there. He did 'Weekend Update.' He’s a part of my comedy consciousness. I feel like I just watched him on Comedians in Cars Getting Coffee. It’s stunning." Thorne-Smith says she was a fan of Macdonald's before her appearance on Late Night. "I’ve always been a fan of Norm Macdonald, which made it extra super thrilling. Yeah, I loved his take on things. That’s why my dad was so taken when Don Rickles made fun of him. When you’re a fan of a comedian and they make fun of you, is there anything better? It’s just heaven, ’cause you’re in their joke. They may be laughing at you, but it doesn’t matter, ’cause you’re in that moment with them." Was Conan concerned she was upset? "How could he possibly have been there with me and not known I was having a good time?" she said. "He’s such a nice man, and I would run into him later and he was afraid that I was offended. I told him absolutely not. You know those great nights you go out with your friends and you start laughing and you can’t stop, and you have that satiated feeling? That’s how I felt. I didn’t expect to have an amazing time, and I had an amazing time. That’s what I walked away with; just giddy with how much fun it was. I had a ball. By the way, Macdonald was prophetic. According to Box Office Mojo, Chairman of the Board grossed less than $200,000 on a $10 million budget." Thorne-Smith and Macdonald reunited in 2000 when she guest-starred on his ABC sitcom Norm.
Norm Macdonald was Tolstoy in sweatpants: "He loved great books, old country music," says Geoff Edgers, who profiled Macdonald in 2016 and who frequently texted with him until as recently as July. "He loved his mother, Ferne, his son, Dylan, and his ever-present producing partner and friend, Lori Jo Hoekstra. (His father died in 1990 and Macdonald’s only marriage ended in the late 1990s.) He had a gift for math and more than a streak of obsessive compulsiveness, which may explain his issues with sports gambling. He could work cleaner than Mister Rogers or bluer than Redd Foxx, depending on what the joke required. Norm’s informal delivery, his ease onstage, could give the false impression that what he did came effortlessly. Fans sometimes even speculated that he was performing drunk, though I never so much as saw him sip a beer in the 15 or so times we were together. The Norm I saw was meticulous about his comedy. There was the concept and there was the execution. Both required deep thought, lots of lined paper and practice. This is how you become so good that virtually everything you do goes viral."
Norm Macdonald mastered the art of being himself: "Keeping things simple was always when MacDonald was at his best," says Brian VanHooker. "Famously, he did a super-clean roast of (Bob) Saget in 2008, rifling off cornball jokes like, 'Bob has a beautiful face like a flower — yeah, cauliflower!' Over the past decade, I’ve rolled my eyes time and again when I’ve seen people refer to this as 'a brilliant piece of anti-comedy,' making use of a trite, nonsense description that MacDonald himself hated. It wasn’t anti-comedy, it was straight-up comedy. Yes, the jokes were bad in that set, but that’s not why they were funny. Norm MacDonald was funny. His delivery in that set was the same as it was in Dirty Work and “Weekend Update,” and that’s why it worked. Besides, MacDonald’s style of joke-telling didn’t come from nowhere. When asked who influenced him, his most common answer was Bob Newhart. If you’re familiar with Newhart’s comedy, it’s easy to see why. Much like MacDonald, his style of delivery was always more important than the actual jokes. His nervous hemming-and-hawing is what made him a household name, and for MacDonald, his hesitating delivery was a big inspiration. Along these lines, I’d like to bring your attention to a piece MacDonald did on a comedy album in 2006, which featured a hilarious sendup of 'The Twelve Days of Christmas.' It was his personal tribute to Newhart’s brand of comedy; it’s nowhere near as well-known as the Saget roast, but it’s right up there in the amount of laughs it delivers."
Norm Macdonald wasn’t normal at all, and nobody was more dedicated to exploiting that abnormality: "When that news broke in the afternoon, every white guy my age used the occasion of Norm’s death to pass around all-time clips of him doing jokes that only Norm Macdonald could have ever pulled off, and to earnestly note that Norm taught them how to be ironic," says Drew Magary. "These were very nice tributes. 'He was a comedian’s comedian' … all that tired s—t. It’s just that there isn’t a man on Earth who would have disdained a 'nice' tribute more than Norm Macdonald, a man who abhorred sentimentality almost as much as he abhorred O.J. Simpson. If you REALLY admired Norm, you would have said, 'Actually, I never cared for the man.' Because Norm Macdonald lived in that avant-garde comedic space where the line between deadpan and serious is so blurry that only a handful of people really got it (NBC exec Don Ohlmeyer infamously never got or liked Norm’s OJ jokes on Saturday Night Live and had him fired from the show in 1998 after four years on the job), and even some of that handful weren’t entirely sure they were getting it. Even I didn’t get it sometimes, and I worked for Norm Macdonald once. Almost a decade after the conclusion of ABC’s Norm (1999-2001), I went a five-day audition to join the writing staff of what would become Sports Show with Norm Macdonald on Comedy Central (which lasted nine episodes). Now that’s one lazya** title for a show. But since Norm named it, it took on a post-ironic color where you could think of it as a brilliant gag and then, five minutes later, wonder if you were a f—king idiot for thinking that. I didn’t get the job."
Macdonald delivered jokes in a way no one else did before him: "The first time you hear it, his odd intonation stops you in your tracks," says John Roy. "You can’t place it: He’s from Canada, but it isn’t iconically Canadian. It’s just … odd. His delivery is almost the opposite of the typical comic, who takes pains to emphasize each precisely ordered syllable. Their voice will go up on the setup, pause for the optimum number of seconds, then hit their punch line loud for maximum effect. Macdonald did none of this; instead, he seemed to actively defy the speech conventions of stand-up. His delivery was somehow casually tossed-off and full of enthusiasm at the same time, like he was so excited to give you these words that he couldn’t bother to arrange them before he released them to the world. Unlike the meticulously composed bits of Jerry Seinfeld, Paul F. Tompkins, or John Mulaney, Macdonald didn’t care if he included ums, repeated words, or you knows. His excitement was contagious, and whatever he lost in polish he more than made up for in conversational naturalism...Macdonald took things we look past every day and found a fundamental absurdity that, somehow, we all missed. When you have insights that original, you can’t worry about cadence or emphasis, you need to get them out now. Macdonald simply saw things differently than almost everyone."
His persona was droll, but he cared seriously, even ebulliently, about what comedy could be: "I was caught off guard by how sensitive he was to creative work generally: he was a serious and studious reader, especially of the Russians, keen to get into the weeds with me about Tolstoy," says Nathan Heller, who profiled Macdonald in 2015. "And he gave off lambent joy about his art. My favorite moment of our day was back in his hotel suite, after the failed expedition, when he spontaneously delivered a kind of craft lesson to his assistant, Steere, an aspiring comic who was working on a bit about dogs. It was a long, winding exchange, but certain turns stuck with me."
Macdonald did not give a f**k about what forces he might run afoul of, sometimes to his great cost: "Today, Macdonald’s 'Weekend Update' stuff is recognizably of a different comedy era," says Kyle Smith. "It feels like forbidden material that was smuggled out by dissidents when the regime was distracted by cracking skulls elsewhere in the cultural empire. There’s a nine-minute reel of Norm’s meanest Hillary Clinton jokes. Norm bashes, slices, sets fire to, and generally destroys Hillary Clinton, and I know what you’re thinking: somebody was mean to Hillary Clinton? On Saturday Night Live? The show that, after one of the funniest moments in U.S. history, the Hindenburg-style crash of Hillary Clinton’s political career in November of 2016, sent out its top talent to sing a mournful ballad in Hillary’s honor?"
Macdonald was always in on the joke, making him one of the truly great smartasses of our time: "The thing about the smartass is that, while he works in shades of irony and deflection, really committing to smartassery requires a truly brave, possibly nuts sensibility," says Jason Diamond. "Thinking something is funny, no matter what other people think, is one thing. Turning that sensibility into a career requires a different sort of commitment: to making a joke that might totally bomb, and then to grinning through it, sitting there as the audience stews in how much they didn’t like the joke, and then repeating the punchline again, defiant. That was what Norm Macdonald did. Nobody committed—while often appearing to not commit at all—quite like him. David Letterman once said that Macdonald 'could be the funniest man in the world'—and the double meaning there, that he might be but also that he might choose not to be—was central to his appeal. There are numerous examples. Macdonald’s most famous impression is probably his Burt Reynolds, tag-teaming with Darrell Hammond’s Sean Connery to make Alex Trebek’s (Will Ferrell) life a nightmare on SNL’s 'Celebrity Jeopardy!' Sketch. For my money, though, the impression to beat is Macdonald’s Letterman, repeating 'Got any gum' over and over. He was doing an imitation of Letterman, a guy who made an art form out of take it or leave it comedy, and putting his own spin on it. His spin, of course, wasn’t too far from the source material besides the fact that Macdonald didn’t look like Letterman or sound like him. It wasn’t a spot-on impersonation—that wasn’t what he excelled at—so much as one comic communing with another who shared his sensibility. He’d often work like this, keep the joke going just because he wanted to. And often times, the repetition became the funniest part about it. (His comedic posture occasionally aged in strange ways: one signature bit wouldn’t hold up today, but might still be the best example of his yearslong commitment to it.)"
Macdonald hated comedy that pandered to a like-minded crowd, once saying in an interview that stand-ups should hunt for laughter, not applause: "His love of pure joke-telling, where craft and timing are far more important than any bearing on reality, is captured in the hours of material from his online show Norm Macdonald Live, during which he would catch guests off guard by having them read offensive lines off printed cards," says David Sims. "As a 'comedian’s comedian,' he landed in hot water after giving an interview in which he sympathized with comics accused of harassment and racism, such as Louis C.K. and Roseanne Barr. (He later walked those comments back.) In that interview, he also offered a surprisingly protective view of traditional stand-up, dismissing other idiosyncratic approaches to the form, which surprised me, given his talent for innovation as a stand-up. But even though Macdonald excelled at challenging expectations and sometimes seemed to revel in the silence following a failed joke, his philosophy was firmly rooted in the magic power that skilled comedians have, to get a rise out of the toughest audience. He hated comedy that pandered to a like-minded crowd, once saying in an interview that stand-ups should hunt for laughter, not applause." As Macdonald once said: “There’s a difference between a clap and a laugh. A laugh is involuntary, but the crowd is in complete control when they’re clapping. They’re saying, ‘We agree with what you’re saying; proceed!’ But when they’re laughing, they’re genuinely surprised. And when they’re not laughing, they’re really surprised. And sometimes I think, in my little head, that that’s the best comedy of all."
Rob Schneider likened his former SNL colleague to jazz legend John Coltrane: "You could tell a joke and it could get nothing, and he could tell that same joke and murder with it,” Schneider said, adding: “Norm would have this incredible ability to tell a joke and you have no idea where it’s going, and then you get lost and you think, ‘Oh man, I know where this is going.' But then the next thing you know, you forget. He was a master of turns and sleight.”
SNL's Darrell Hammond recalls Macdonald being a no-frills kind of guy: "He wasn't seeking fame and he wasn't seeking fortune or power. He just was living his life, trying to be funny," Hammond said. "And so when you're around him, it seemed so unremarkable at the time, it was just Norm being funny and being him — which was no filter between your brain and your mouth, and you say the thought that is formed on the way out."