At the Emmys, John Oliver said 'no one was funnier' than Norm Macdonald. Here's why we agree

·6 min read

My favourite Norm Macdonald joke €" and trust me, there is serious competition €" is one he told as anchor of Weekend Update on Saturday Night Live in the late 1990s. Papers in front of him, he reported with a cheer: "Yippie! Jerry Rubin died this week." Looking down, he apologised for his mistake, and tried again: "That should read: 'Yippie Jerry Rubin died this week.'"

Silly, dark, ruthlessly concise, this gem is a model of craft, and like many of Macdonald's bits, it proves how the smallest change in tone, language or, in this case, exclamation mark can radically shift meaning, providing the kind of jolt of surprise that produces belly laughs.

Macdonald, who died on 14 September of cancer, maintained a studied modesty about his work. He said that his act had no substance, that it was all "gossip and trickery." And he claimed without self-pity that he would be remembered only for his few years at Saturday Night Live, not his decades of stand-up, which he referred to as "a shabby business, made up of shabby fellows like me who cross the country, stay at shabby hotels, and tell jokes they no longer find funny."

He described his life as a sprint to outrun the wolves of irrelevancy. "They caught and devoured me years ago," he wrote in his 2016 quasi-memoir, Based on a True Story.

Whether he believed this about himself does not matter (Macdonald was a very skillful liar), and there is some merit to his points about stand-up and his credits, but the ornate way he beats himself up hints at a deeper truth: 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.

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 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 OJ 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 the final week of his show. 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. You see this in his Saget roast: the conviction to push through despite the confusion of the response. He pleased the crowd without being a crowd-pleaser. And no one had a nimbler and more assured sarcastic voice, which he used to find humour in ambiguity. There was a wonderfully odd moment on David Spade's talk show a few years ago when Macdonald told Jay Leno he was maybe the best talk-show host ever, and no one, including Leno, seemed to be able to tell if he was being sincere.

There is a lot of fun to be had in this liminal space between earnestness and just kidding. One of Macdonald's most impressive feats is writing an entire memoir that remains there. It is one of the greatest comedian memoirs but also a pointedly frustrating mix of fact and fiction, cliché and originality. It is very funny, sometimes tedious, occasionally wise. The title, Based on a True Story, is not just a gag. It is rooted in his faith that, as he puts it, "there is no way of telling a true story. I mean a really true one, because of memory. It's just no good."

Just because you cannot tell a really true one does not mean that art cannot get closer to the truth. In an interview with New York Magazine, Macdonald balked at the trend toward confessional art, saying he thought art was supposed to be about concealment. That was revealing.

The fact that Macdonald struggled with cancer for a decade was something he certainly did not advertise in his work. His death came as a shock to many. But clues were everywhere. Death has been among his favourite subjects in recent years. In a great viral moment, he delivered one of the earliest and best comedy club sets about the coronavirus. It was at the Improv in Los Angeles in March 2020 right before venues were shutting down. "It's funny that we all now know how we're going to die," he said. "It's just a matter of what order."

At the start of his memoir, he tells a story about reading on his Wikipedia page that he had died. Then he imagines if it were true, laughing until a thought stops him cold. "The preposterous lie on the screen before me isn't that far off," he wrote. This seemed like jokey melodrama when I first read it, but now it hits differently.

Macdonald once talked about an uncle dying of cancer, skewering how we now describe people suffering from that disease as "waging a battle" because that means the last thing you do before you die is lose. "I'm not a doctor, but I'm pretty sure that if you die, then the cancer also dies at the same time," Macdonald said on Comedy Central. "That to me is not a loss. That's a draw."

Jason Zinoman c.2021 The New York Times Company

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