Norm Macdonald's funniest SNL moments, from Celebrity Jeopardy to Weekend Update

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Norm Macdonald's distinctive comedy spanned many decades and forms, from absurdist memoirs to long stories about depressed moths. But the beloved comedian, who died Tuesday at age 61, was always best known for his five-year run as a cast member on Saturday Night Live.

"Today is a sad day," a representative for the show said in a statement following Macdonald's death. "All of us here at SNL mourn the loss of Norm Macdonald, one of the most impactful comedic voices of his or any other generation. There are so many things that we'll miss about Norm — from his unflinching integrity to his generosity to his consistent ability to surprise. But most of all he was just plain funny. No one was funny like Norm."

Mary Ellen Matthews/NBCU Photo Bank/NBCUniversal via Getty Images Norm Macdonald at the 'Weekend Update' desk on 'Saturday Night Live'

Indeed. During his time at the venerated sketch show, Macdonald created its iconic spoof of Celebrity Jeopardy, performed several hilarious celebrity impressions (most famously Burt Reynolds), and spent three years as anchor of Weekend Update, where he made an indelible mark with his unique and defiant sense of humor. (Often, when a joke would fall flat or draw gasps and boos from the audience, an unfazed Macdonald would simply smirk, stare into the camera, and move on to the next one.)

Macdonald was known for farcical non sequiturs (often involving Frank Stallone) and envelope-pushing black comedy, and for eviscerating certain celebrities, including Michael Jackson. But his ire was most often, most bitingly, and most famously directed at O.J. Simpson, whose media-circus murder trial played out during Macdonald's tenure at the Update desk.

"Well, it is finally official: Murder is legal in the state of California," Macdonald declared after Simpson's acquittal in October 1995. Of course, that didn't stop him from continuing to skewer Simpson after the trial ended. Many believed this was the reason for Macdonald's dismissal from SNL in 1998, as then-NBC executive Don Ohlmeyer was a longtime friend of Simpson. (Ohlmeyer disputed this, saying he fired Macdonald simply because he wasn't funny.)

Perhaps Macdonald's most beloved SNL moment, however, came after he departed the show. When he returned to host in 1999, the comedian reprised his role as Burt Reynolds on Celebrity Jeopardy, once again tormenting Will Ferrell's exasperated Alex Trebek. The sketch, which EW once included in a feature called "Build a Perfect SNL Episode," features Macdonald's Reynolds demanding Trebek call him "Turd Ferguson," reading "A Petit" as "Ape tit," and wearing an oversize hat ("It's funny because it's bigger than a normal hat!"). Of the many Celebrity Jeopardy entries, it's most frequently cited as the best.

While hosting, Macdonald also took advantage of the opportunity to razz SNL in his opening monologue. (The monologue is unavailable in full on YouTube, but you can stream it on Peacock.) Recalling how he had been fired because he "wasn't funny," Macdonald said, "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?… Then it occurred to me: I haven't gotten funnier! The show has gotten really bad!"

The joke drew both applause and boos from the studio audience — perhaps the most fitting way to sum up Macdonald's polarizing comedy. If it wasn't suited to all tastes, it undoubtedly left a legacy that will reverberate through entertainment for years to come.

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