Comedy lost one of its most individual personalities on Tuesday, September 14th, when Norm Macdonald passed away after a nine-year battle with cancer. 

Whether it was as the most singularly imposing host of Saturday Night Live’s Weekend Update or as the type of talk show guest hosts always wanted to be on their couch or as one of the most biting stand-ups to ever do it, Macdonald was a titan of comedy for three decades.

The amount of gushing tributes pouring in from the comedy world, with late night hosts clearly devastated, is testament to his influence and impact.

There’s no better way to mark his legacy than by remembering his finest and funniest comedy. Check out our list of the greatest Norm Macdonald moments below.

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The Update host v. O.J. Simpson 

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Macdonald had the pleasure of leading SNL’s Update desk when some of the biggest news stories of the 90’s were breaking in the U.S.. Bill Clinton’s troubles copped a lot of heat from the comedian but it was his diatribes aimed at O.J. Simpson that really captivated audiences.

“Well, it’s finally official: murder is legal in the state of California,” Macdonald sardonically declared after the acquittal of the infamous actor in 1995. He kept Simpson in his firing line throughout his Update tenure, with many believing his firing from SNL in 1998 was mainly due to this (then-NBC executive Don Ohlmeyer was a friend of Simpson, go figure).

Dunking on Carrot Top 

Macdonald was a beloved talk show guest on his own gut he was equally good at bouncing off other guests. When Courtney Thorne-Smith’s segment appeared to be lacking, he jumped into life, skewering her upcoming film. When host Conan O’Brien asked about shooting with prop comic Carrot Top, Macdonald didn’t miss a beat.

“If it’s got Carrot Top in it, you know what a good name for it would be? Box office poison.” When Smith then revealed that the film’s name was Chairman of the Board, the razor-sharp Macdonald was never going to miss his opportunity. “I bet that board is spelled b-o-r-e-d,” he said to howls of laughter.

Return as SNL host

Not long after being dismissed from the show for allegedly being not funny, Macdonald was surprisingly asked back to host SNL in October 1999. His opening monologue went just as you’d expect, the elephant in the room not so much being addressed as being wildly ridden, bouncing and destroying the walls. “I don’t know if you remember this, but I used to actually be on this show,” he slyly started, before addressing the supposed fact that he wasn’t funny.

“But now, this is the weird part, right? It’s only a year and a half later and they asked me to host the show! So I wondered, I go, ‘Hey, wait a second here. How did I go, in a year and a half, from being not funny enough to be even allowed in the building, to being so funny that I’m now hosting the show? How did I suddenly get so goddamn funny?’ It occurred to me, I haven’t gotten funnier. The show has gotten really bad!”

THAT Burt Reynolds impression

Amongst the best recurring SNL sketches is Celebrity Jeopardy: hosted by a befuddled Alex Trebek played wonderfully by Will Ferrell, it’s allowed so many hilarious characters to compete, particularly Darrell Hammond as the rascal Sean Connery. It’s Macdonald’s larger-than-life portrayal of Hollywood royalty Reynolds, though, that always steals the show.

Both arrogant and nonchalant, perpetually-gum chewing, sporting a ridiculous oversized cowboy hat, he’s impossible to ignore. Just try not to laugh at him insisting that his name is now Turd Ferguson.

A present for Conan

Like we said, talk show hosts loved Macdonald for a reason, probably none more so than Conan O’Brien. As the chaos of Conan’s time as host of the Tonight Show came to a sorry end in January 2010, Macdonald stopped by in one of its final episodes, bringing along a gift basket for the host. “Congratulations, Conan, on finally securing your place as permanent host of the Tonight Show,” he read out completely deadpan.

“That’s something they can never take away from you. Sure, the pressure is on. But if I know you, Conan O’Brien, miserable failure is not an option.” Just an ingenious mixture of sincerity and insincerity, heart and acerbity. There’s very few comedians who could have made such a joke.