There’s a bit about doctors in Norm Macdonald’s Hitler’s Dog, Gossip and Trickery (2017)—easily one of the funniest, weirdest and most impressively unclassifiable stand-up specials on Netflix—that just plays differently, now that we know that the man had been fighting cancer for the better part of a decade. It’s classic Macdonald; bone-headed and yet, undeniably hilarious, accentuated by his carefully careless, hands-in-pocket delivery.

“Doctors are too preoccupied by disease, what they should really be working on is death. You go to a doctor and they say, ‘well, we got rid of your arthritis’. And then you go, ‘am I still gonna die?’ and they say, ‘yes.’ Never made sense to me!”

The 61-year-old Canadian comedian died of cancer on Tuesday, prompting tributes from some of the best-known comedians and comic actors in the business. Macdonald’s time at Saturday Night Live (SNL), his distinctive standup sets down the years, and his status as a witty, effervescent guest for the likes of Conan O’Brien and company, were all fondly remembered. 

Hindsight is 20-20, of course, but in retrospect the bit from Hitler’s Dog is eerily reminiscent of one of the first funnysad jokes in his book Based on a True Story: Not a Memoir (2016). When Macdonald’s agent informs him in 2013 (the cancer diagnosis had happened by then) that a prankster has changed his Wikipedia page to claim his death, the comedian laughs at first. And then he freezes up, thinking about his mortality, his ageing body. “Then a thought comes to me in a sudden, a thought that stops all my laughing, makes me real cold, and has me craving a couple of grains of morphine, or at least some whiskey. And the thought is this: The preposterous lie on the screen before me isn’t that far off.(…)To misquote Twain, it turns out the rumor of my death is only slightly exaggerated.”

Perhaps riffing off the Mark Twain reference in that last line, Louis CK (in his foreword to the book) called him the only comedian ever to match Twain’s satirical brilliance. Macdonald was a deceptively literary comedian; I say ‘deceptively’ because at some level his entire act (much like, say, Nate Bargatze’s these days) was based upon un-pretentiousness and playing a certain kind of folksy Everyman character, a pre-modern Ted Lasso figure if you will. In a great little moment from Hitler’s Dog, he describes scoping out parties for “other simpletons” like him. “You know how they say guys have ‘gaydar’ — they can see other gay people? I’m like that with guys at my same level of smartness. I’ll spot a guy in the corner and immediately, I’m like, ‘I can keep up with that motherfucker!’ And then we talk about Jughead comics for two hours.”

People like Norm Macdonald are why stand-up comedy is seen and reviewed as a serious art form today.

This shtick did not always cloak his erudition, however, especially outside of his stand-up work. In one of his few flare-ups on Twitter, Macdonald memorably skewered the American writer Bret Easton Ellis in 2013. Ellis’s offense was taking cheap snarky shots at the much-loved short story writer (and Macdonald’s fellow Canadian) Alice Munro. Macdonald fired back, “Alice Munro is to literature what Lee Iacocca is to selling automobiles. Bret Easton Ellis is to literature what Lee Iacocca is to literature.” In Based on a True Story, there are minor mic-drop moments everywhere you look, stuff like “The plain truth is that Adam Eget is an alcoholic and that’s why he doesn’t drink. Me, I’m not an alcoholic and that’s why I do drink. Life sure is funny that way.”

From writing for shows like Roseanne in the 90s to his SNL years to headlining his own sitcoms and talk shows, a few things remained constant with Macdonald: his dedication to the craft of comedy, his self-deprecation (“most of my comedy is gossip and trickery”, he said, in a line that gave his Netflix special its name) and his willingness to push a joke well beyond the point that audiences (or even his comedic peers) expected. That last bit is evident not only in his legendary ‘moth joke’ on Conan’s couch (if you haven’t watched it, you really must), but also during his appearance on Bob Saget’s Comedy Central Roast in 2008.

The Comedy Central Roasts have been criticised in the past for being formulaic, comedians trading ever-escalating insults that take on darker and darker tonalities. As though protesting this, Macdonald reeled off stale, done-to-death routines seemingly from the 1950s and 60s, in a monotonous, unwavering voice that had his fellow comedians howling onstage (even though the audience wasn’t really into it). Watch Andy Samberg trying his best to pull off a similar stunt during James Franco’s roast in 2013 and you’ll see Macdonald’s handprints all over the routine; this was a comedian’s comedian.

Of course, the man had his missteps, too. He made a string of transphobic jokes throughout the 90s, none worse than his “Brandon Teena deserved to die!” line (Teena was a trans man who was murdered in 1994; the case gained widespread attention after Hilary Swank played Teena in the 1998 film Boys Don’t Cry). However, he also apologised for the same more than once during interviews, saying that he acknowledged that jokes like his could lead to anti-trans violence. Crucially, he made a distinction between a joke being “offensive” and being “hurtful”, respectively; in his view the latter kind was harmful and led to violence against already oppressed groups. “It doesn’t matter if the whole world is laughing at your joke, if it’s hurting even one person it’s a bad joke or there’s something wrong with your delivery”, he said.     

People like Norm Macdonald are why stand-up comedy is seen and reviewed as a serious art form today, to an extent. He could make you laugh when you least expected to, when he was saying and doing perfectly innocuous things; that’s something that can’t be taught, not really. No doubt he’s regaling the angels right now, probably with a long yarn about some dodgy dessert he ate last year. Fare thee well, Norm.