Norm Macdonald was a stand-up and SNL legend, not to mention a fine comedic actor when given the shot to do his own thing. But it truly was must-see TV when he was invited to someone else’s party, whether as a guest or, infamously, awards-show host. Mixing rambling stories, zingers, anti-comedy bits, and just interacting with whomever happened to be sitting next to him, Macdonald always slayed (and occasionally burned some bridges). In honor of his shocking death at 61, here’s a collection of his best, most subversive guesting moments, from the all-time great Courtney Thorne-Smith sit-down to his skewering of the ESPYs.
Norm’s “Logic Professor” Neighbor (1996)
Here’s one of those classic Where does he come up with this stuff? tales from Norm. Here, he tells Conan O’Brien about his neighbor, a professor of logic at the University of Science. The long buildup with the quick, dumb turn at the end makes it feel like a precursor to the Moth Joke years later.
Norm Steals the Show From Courtney Thorne-Smith (1997)
Poor Courtney Thorne-Smith just wanted to promote her new movie with Carrot Top on Conan O’Brien’s show, and Macdonald decided to stick around for a little fun. Like a shark smelling blood in the water, he can’t stop himself from just ripping Melrose Place and the ginger prop comedian, and then when O’Brien tells him to “do something” with the title of her movie, Chairman of the Board, Macdonald doesn’t miss a beat: “I bet the board is spelled B-O-R-E-D.” It might be the hardest Conan’s laughed on any of his shows.
“You Got Any Gum?” (1997)
In this montage, you get to see young Macdonald doing his definitely not-great David Letterman impression on SNL and then being forced to do it in front of the man himself. For a second there, you almost think he’s going to crack under the pressure, but nope.
Norm’s Scrabble Story (1998)
Macdonald’s bizarre yarns like this one he told Letterman about playing Scrabble at a B&B with Old Harold Delaney make you wonder how many weird characters he actually met and how much of this just came straight from his twisted brain.
Norm at the ESPYs (1998)
Macdonald’s hosting gig at the sports channel’s awards show came a month after his 1998 firing from SNL, and you can see that he didn’t take it any easier on the athletes there than he did on celebs during his time behind the Weekend Update desk. Of course, he had to end it with an O.J. joke …
Norm Rants About Viagra (1999)
Within 90 seconds, you’ll lose count of how many times Macdonald says “cock.” It gets lewder from there in this, er, seminal bit from Dennis Miller Live .
Norm on The View (2000)
“Oh, Bill Clinton, he murdered a guy!” Those seven words and the innocent puppy act Macdonald pulls as the panel of View hosts, particularly Barbara Walters, yell at him make this a perfect minute of live TV.
Norm Loses on Millionaire (2000)
When Macdonald went on a celebrity version of Who Wants to Be a Millionaire? in 2000, he got the whole way to the final question. He was just about to get it right but then got psyched out by Regis Philbin, not wanting to lose a few hundred thousand for Paul Newman’s charity, The Hole in the Wall Gang. You can tell how much it bothers Macdonald, who had a serious gambling addiction throughout his life.
Norm Talking Crocodile Hunter on The Daily Show (2006)
A lot of Macdonald’s late-night appearances differed from his un-PC, “too soon” Weekend Update bent. Not this one. Here, he decided that the death of Steve Irwin — which had happened ten days earlier — was the topic he needed to discuss on that night’s Daily Show. Even this many years later, we can all feel like Jon Stewart: “Please don’t make me laugh at this.”
Norm’s Bob Saget Roast Bomb (2008)
Roasts have a formula: Viciously shit on everyone along the dais, then say something nice to the guest of honor at the end. Macdonald, at Bob Saget’s Comedy Central roast, decided to just go with the tamest, lamest quips for a solid six minutes, explaining some of the punch lines along the way. It’s a daring, genius feat that highlights how stale roasts had gotten by then, with everyone just trying to be the dirtiest comic of the night.
Norm’s Bob Uecker Story (2009)
To be a friend of Macdonald’s meant you had to endure a relentless amount of ball-busting. On this Letterman appearance, Macdonald sells out one of his pals, Milwaukee Brewers broadcaster Bob Uecker, with a profane story involving Creedence front man John Fogerty.
Norm as Captain Sully (2009)
After seven minutes of Macdonald and Conan O’Brien just riffing off each other on the topics of the day, the two finally get to the sketch where Norm debuts his biopic of the famous pilot before the Miracle on the Hudson. The best part is when he flubs a line and yells, “I wrote this bit 25 minutes ago!”
Norm Sends Off Conan’s Tonight Show (2010)
Far different from his Letterman good-bye, Macdonald has to get his digs in, reading a card to O’Brien that he had written months earlier: “You are the king of late night! Long live the king!”
Norm Tells a Great Rickles Story (2011)
It made so much sense that Macdonald would enlist Don Rickles for his movie Dirty Work, but as he tells Jimmy Kimmel, the elder comedian couldn’t remember his lines. But Rickles, via Macdonald’s retelling, gets the best punch line of this clip.
Norm Talks Kinison and Dangerfield (2011)
It’s not the funniest Macdonald bit, and it’s not technically a TV appearance but it’s quite interesting to hear him tell Howard Stern about two of his biggest influences: Sam Kinison and Rodney Dangerfield. While talking about Dangerfield, Macdonald, for once, does a pretty accurate impression.
The Moth Joke (2014)
If you say “The Moth Joke” to any Norm or Conan fan, they’ll know what you mean — a detailed, depressing saga of an Eastern European moth, stretched so long that even O’Brien can’t stand the tension. Then, the payoff comes, one of the dumbest and funniest punch lines you’ll ever hear.
Norm’s Final Letterman Appearance (2015)
Twenty-five years after his first performance, Macdonald returned to Letterman for a long set that included an extended bit about World War II. Then, briefly choking up, he gets genuine, reciting an old bit of Dave’s and ending with this heartwarming tribute: “Mr. Letterman is not for the mawkish, and he has no truck with the sentimental. But if something is true, it is not sentimental. And I say in truth, I love you.” Cue the waterworks.
Norm’s Sick, Slow Burn (2016)
Another drawn-out joke, another friend thrown under the bus. You know what’s going to happen as he sits down with the Grown Ups crew on Conan, but Macdonald’s punch line here is just perfect.
Norm’s Larry King Interview (2016)
This Larry King Now conversation features some of the deepest stuff you’ll ever hear from Macdonald. It’s especially interesting to hear him talk about death and religion, considering we now know he had cancer at the time of this interview.
Norm Talking Kojak and Hookers With Seinfeld (2017)
This Comedians in Cars Getting Coffee tidbit highlights a few things that were great about Macdonald comedy: He never put any effort into impressions, you never knew where he was headed, and he always loved tagging on a wholly unnecessary explanation.