For those outside the loop of comedy news, Norm Macdonald probably seemed like an unspectacular choice to host Saturday Night Live: He was far from an A-level celebrity, and his latest projects (the box office flop Dirty Work, his soon-to-be-short-lived series The Norm Show) didn’t exactly light the world on fire.

But the real-life context behind that selection — and the awkwardness that accompanied it — made for time-capsule television on Oct. 23, 1999.

Macdonald had been part of SNL from 1993 to 1998 — best known for co-writing (with Jim Downey) and delivering the regular “Weekend Update” segments, which examined recent headlines through deadpan punchlines and non-sequiturs that often flew over the audience’s heads. That perplexed viewership reportedly included NBC's west coast president, Don Ohlmeyer, who removed Macdonald from “Update” following the Dec. 13, 1997 installment; after a few more months — a strange time in which the comic only popped up in traditional sketches — he exited the show altogether.

During that fragile in-between period, Macdonald made the late-night rounds, including a now-classic appearance opposite his idol, David Letterman, on The Late Show. The host drilled Macdonald about his “Update” removal, even questioning why he’d continue to stay on the program at all. The SNL veteran smiled and stammered in response, seemingly taking the whole thing in stride. But he did couch some clear frustration into his jokes, especially when noting his disdain for sketch acting.

Watch Norm Macdonald Talk 'SNL' With David Letterman on 'The Late Show'

“Now they’re saying, ‘Oh, we’ll put you in a whole bunch of sketches,’ which I don’t want to be in!” he said. “Then they’re like, ‘Here, you’re the scientist in charge of monkey boy or some damn thing. I’m running in, going, ‘Hey, cheerleaders, what’s going on? I haven’t seen monkey boy!”

Macdonald, after some prompting from Letterman, also addressed a seemingly uncomfortable phone call with Ohlmeyer — and, in the process, foreshadowed the comedic tone of his SNL host gig.

“He goes, ‘Oh yeah, I’m firing ya, there, from the show,’” Macdonald noted in his signature aw-shucks delivery. “I said, ‘Oh, that’s not good.’ I said, ‘Why’s that now?’ He said, ‘You’re not funny.’ I said, ‘Holy lord, that’s even worse news. I don’t got nothing to fall back on.”

Few could have predicted the role reversal of Macdonald, well over a year from his full departure, returning to the stage. Given the abrupt shift, an obvious layer of irony surrounded the spot — a fact he addressed, hilariously, in the episode’s opening monologue.

“When the people here asked me to do the show, I gotta say I felt kinda weird, ya know?” he told the crowd. "I don’t know if you remember this, but I used to actually be on this show. I used to do the ‘Weekend Update’ news routine. You remember that? That’s where I did the make-believe news jokes. That was me! So then, a year and a half ago, I had a sort of disagreement with the management at the NBC. I wanted to keep my job, and they felt the exact opposite.”

The reason? “They said that I wasn’t funny.”

Hear Norm Macdonald's 'SNL' Opening Monologue

“Now with most jobs, I could have had a hell of a lawsuit on my hands for that,” he continued. “But, see, this is a comedy show. So they got me. [Laughs.] This is the weird part: It’s only a year and a half later, and now 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 was inexplicable to me because a year and a half, let’s face it, is not enough time for a dude to learn how to be funny.”

“Then it occurred to me,” he added. “I haven’t gotten funnier; the show has gotten really bad! So yeah, I’m funny compared to…well, you’ll see later. OK, so let’s recap: The bad news is I’m still not funny; the good news is the show blows! Alright, folks, we’ve got a bad show for you tonight!”

Pretty much no one remembers the rest of that SNL episode — and for good reason. Macdonald, in an almost avant-garde hybrid of self-sabotage and revenge roasting, threw a comic grenade both behind him and in his own path.

“I was gonna do a thing that I thought would be really cool, but I was talked out of it,” the comedian told The Huffington Post years later. “I was going to do the monologue and then leave and let them do the rest of the show by themselves, which I thought would be good for the show because they’d have to band together and work around the fact that the host wasn’t there.”

He didn’t need to pull such a stunt. As usual with any room he occupied, Norm earned the last laugh.

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