Norm Macdonald plus Conan O’Brien equals comedy gold

If you were to go onto Team Coco’s announcement of who the final guests for Conan would be, you’d be met with a chorus of comedy nerds screaming one thing into the ethers “Where is Norm???”

They are referring, of course, to Norm Macdonald’s legendary appearances with Conan O’Brien. All a great talk show host needs is an equally great guest to send things from great to epic. And that’s just what happened whenever Macdonald would appear with O’Brien from 1993 until his last appearance in 2016, in what is arguably one of the best host/guest dynamics of all time. Was Macdonald’s material on Conan anything extraordinary different than when he went on other talk shows? Of course not. His hilarious style of having no discernible style and putting no effort in whatsoever was on display as much as ever. But O’Brien knew just how to play into this and call Macdonald out on it, resulting in the perfect fodder for late night laughs.

We figured you can’t say goodbye to O’Brien’s late night career without touching on some of our favorite appearances that Macdonald made over the years.

The Moth Joke

What other show would allow a guest to tell a meandering joke that they “heard in the car on the way over” and goes basically nowhere? Macdonald’s infamous “moth joke” is akin to a great work of art. Not unlike his set on Bob Saget’s roast, the joke itself is painfully unfunny. It’s the delivery and what Macdonald does with it that makes it a slam dunk all the way.

Norm and Courtney Thorne-Smith

Right around the time Courtney Thorne-Smith was leaving Melrose Place, she made an appearance on Late Night. As he would usually do, Macdonald scooted down the couch for her segment and proceeded to chime in whenever he saw fit. This was commonly known as “Norm saving the interview.” However, once her co-star in a forthcoming film Carrot Top’s name came up, Macdonald was like a dog who wouldn’t let go. When he found out the name of the Carrot Top vehicle was Chairman of the Board, he chimes in “I bet the board is spelled B-O-R-E-D.” Genius.

Norm Macdonald and Roshumba

Another case of Norm sticking around for the next guest, this one is a little more obscure but a personal favorite of ours. When a super-model named Roshumba came on the show, Macdonald went the opposite way of how you might expect him to act: He was incredibly uninterested and checking himself out in the monitor. And while some of the segment would be deemed as politically incorrect these days (specifically Norm’s advice for being a model), it still manages to make us laugh every time all the same.

Norm Cooks with Gordon Ramsay

It didn’t take long at all for Norm to start pushing Gordon Ramsay’s buttons. As great as he is chiming into interviews, the real gold seems to be having him participate in a cooking segment. Norm’s “I don’t give a sh*t” attitude seems to counter with Gordon’s angry passion for all things cooking quite nicely. Just watching Norm try to segment an orange has us in stitches. It finally gets to the point where O’Brien grabs the bottle of wine that was there for the segment and starts drinking while asking “Why are we even having a cooking segment at this point?” The fact that any end-result product was made is actually quite remarkable.

Conan Brings A Gift Basket

As Conan O’Brien’s version of The Tonight Show was coming to an end, Norm decided he’d pay his respects by coming by with a gift basket he bought the talk show host… 7 months earlier. He proceeded to read a card that included lines like “If I know you, Conan O’Brien, miserable failure is not an option.” Despite it being such a dark time in O’Brien’s career, the look on O’Brien’s face throughout is one of clear amusement at the absurdity of it all. And no one can bring that out quite like Norm.

Norm on porn, The Dating Game, and the Olympics

A more traditional talk show appearance, but nonetheless still a hilarious one. Here, Norm talks about the difference between the films Pulp Fiction and Pump Friction, why porn should have a blooper reel, stupid guys on The Dating Game, and the combining of sports in the Olympics.

Norm is a Deeply Closeted Gay Man with a Battle-Axe Wife

Even when he has a book to promote, he can’t help going off the rails. During the interview, Norm talks about being a “deeply closeted gay man,” but Conan seems to misunderstand what that actually means. In fact, he does have a wife and she is a “real battle-axe.”

Norm Ruins the Promos

Just because it didn’t make it on the air, doesn’t mean it didn’t happen. In a behind the scenes video, we see just how frustrating it is trying to rein in Macdonald’s giddy distractions when it comes to shooting some local promos. Next time, something tells us they wound up filming them after he left the building.

Norm Has an Andy Richter Joke

While Norm was in Atlanta, he allegedly met a guy on the street who had a joke about Andy Richter being a Swedish German. And much to Conan’s dismay, Norm tells the joke to the delight of everyone in the crowd. The joke involves an old prospector unable to find a woman, but he can find Andy Richter, the Swedish German.

Norm has a Hooker Story

When Sean Hayes was on Late Night, he apparently shared a story about a hooker. While Norm didn’t share his own experience, he did send the show once again off the rails with a touching story about the time a buddy of his got ripped off by a hooker. It quickly turns blue, and unfortunately he forgets the rest of his buddy’s story, but what we do hear is classic Norm.

The Turtle Joke

We started with a moth joke, so why not end with a turtle joke. Because who doesn’t love a good turtle joke? When O’Brien asks Norm about his bartending days, he shares a story about a drunk guy who was playing darts, and after he won, Macdonald gave him a shoebox with a turtle in it. We’re not gonna spoil the punchline, but it goes not where you think it’s going to go and also exactly where you think it’s going to.