Norm MacDonald

So I says to the guy I says to the guy I says...

—Norm Macdonald

What happens when a Deadpan Snarker and a Cloudcuckoolander have a kid. Oh, and they're both nihilists. Well, that or The Joker. Wait, Norm MacDonald was The Joker!

Norm MacDonald (1959-2021) was a Canadian-born comedian who started on Saturday Night Live. Though he appeared in sketches on the show (his impressions of Burt Reynolds and Larry King were hilarious), he was most widely known for the "Weekend Update" segment, which was considered by many critics and viewers to be the only reason to watch Saturday Night Live when it was limping to the barn with Seasonal Rot during the show's 20th season. After a rather ignominious split from the show, he did some movies and TV shows. His appearances on late night talk shows were quite popular, for he has a tendency to lampshade the tropes of whatever medium he is currently operating in.

He was perhaps foremost a master of Anti-Humor. His comedic method can usually be distilled down to a three step process:

Tell Joke.
Joke is so cheesy, it's bad.
It's so bad, it's good.

One of his later projects was a sports show on Comedy Central called Sports Show with Norm MacDonald. It was basically his old "Weekend Update" style, 'cept about sports, and naturally, Too Good to Last.

Norm MacDonald provides examples of the following tropes:

Captain Obvious: An essential ingredient of his style and the point on which most people's mileage will vary. Part of what makes it work is what he chooses to be obvious about.
- He's obvious about things that are so obvious that we just don't even think about them anymore. Like saying that scientists should start focusing on this death thing.
Cloudcuckoolander: His take on Larry King.
I Want You to Meet An Old Friend of Mine: Norm was often involved in projects with by Adam Sandler, Dennis Miller and Artie Lange.
It Will Never Catch On: The accusations from NBC that Norm simply wasn't funny come off this way when you consider this: his first appearance on SNL after the Weekend Update debacle (note that Norm was only fired from the sketch, not the show, so he had infrequent appearances for months afterwards) was during guest host Sarah Michelle Gellar's monologue. He was immediately greeted by a massively positive audience response - interrupting the skit for several moments. And just to hammer it home, Norm wound up hosting an episode himself a year-and-a-half later.

"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?"

Non Sequitur: Nearly every week one of his news stories would "support" the conclusion that Germans Love David Hasselhoff. The only exception to this was when he got Hasselhoff to appear on the set and read a card saying "Germans love me," which quite reasonably supported his theory.
Running Gag: Several on Weekend Update. The most memorable ones being Norm MacDonald's relentless insistence about OJ Simpson being guilty (ending with "This just in, murder is now legal in California"), his weird story of the week which involved, you guessed it, Frank Stallone, and his "Notes to Self" reminding him to shamelessly exploit stupid things happening in the news.
Screwed by the Network: Norm's removal from Weekend Update. Now, it was claimed that it was simply because he wasn't funny (which ran counter to the opinions of critics and the studio audience). However, as noted above, OJ Simpson was a frequent source of material for Norm on Weekend Update and Simpson happened to be a friend of Don Ohlmeyer, NBC's West Coast Executive. Many suspect that Ohlmeyer was angered by Norm's jabs at Simpson and subsequently demanded his removal.
- Summed by Norm when he hosted:

"I had sort of a disagreement with the management at, uh, at the NBC. Uh, I wanted to keep my job, right? And they felt the exact opposite."

Too Soon: As a guest on The Daily Show, he unapologetically cracked jokes about the death of "Crocodile Hunter" Steve Irwin just after it happened. Jon Stewart practically begged him to stop... while fighting back fits of laughter.
Wrong Genre Savvy: In the Celebrity Edition of Who Wants to Be a Millionaire?, part of his strategy was trying to find Regis' tell for a correct answer, like in a poker game. Regis didn't know the answers either, though Norm did end up winning $500,000.