‘I Drinks a Bit’: Every Norm Macdonald Appearance on Conan O’Brien Shows, Ranked

Rob Schneider never saw #3 coming
‘I Drinks a Bit’: Every Norm Macdonald Appearance on Conan O’Brien Shows, Ranked

Two years ago, on September 14, 2021, Norm Macdonald passed away after a decade-long private battle with leukemia. Since then, the hunger for Macdonald content hasn’t subsided, as myriad YouTube clips and social media tributes can attest to. Among the fan-favorite appearances are his numerous visits to Conan O’Brien’s talk shows. With 25 guest spots across Conan’s three shows, we’re ranking all of Macdonald’s segments by sheer hilarity...

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‘Go On! Get Out of Here, You Dirty Bum!’

Show: Late Night with Conan O’Brien 

Date: August 27, 1996

Macdonald’s ninth appearance on Conan’s first show is just fine. He talks about Bob Dole, kickboxing and accidentally giving his subway token to an unhoused person. It’s not unfunny, but it doesn’t measure up to everything below. 

‘Hot property’

Show: Late Night with Conan O’Brien 

Date: February 23, 1995

Macdonald did a stand-up set on his second Late Night appearance, then had a conversation with Conan for the first time. His set was mainly about Star Search, including an impression of Ed McMahon. His interview segment included a joke about O.J. Simpson — I’m sure to the ire of NBC executive Don Ohlmeyer — and some talk about Billy Madison. While it’s pleasant, it’s still difficult to see how Macdonald will become Conan’s funniest recurring guest.

‘I’ve Got Too Many Teeth, That’s the Problem’

Show: Late Night with Conan O’Brien 

Date: June 13, 1995

Macdonald did a pretty funny set about his teeth for his third Late Night go-around.

‘I Love Kelly… Gretchen… I Mean I Love Gretchen’

Show: Conan

Date: November 15, 2011

Macdonald was a five-time guest on Conan’s TBS show, with this appearance being his third. It’s a good — if not the best — example of him interrupting another guest and them having no idea how to cope. This time, his victim is Olympic snowboarder Gretchen Bleiler, whom he originally calls “Kelly.” (Starts at 12:45 in the clip above.)

‘Pump Friction’

Show: Late Night with Conan O’Brien 

Date: November 9, 1995

MacDonald’s fourth appearance on Late Night with Conan O’Brien foreshadows future guest spots. He tells a long, winding story about accidentally ordering a porn called Pump Friction instead of Pulp Fiction, then hilariously describes The Dating Game. It doesn’t pay off in a great punchline, but it’s still very “Norm.”

‘I’m a Professor of Logic’

Show: Late Night with Conan O’Brien 

Date: October 9, 1996

Macdonald tells one of his trademark long, seemingly-time-wasting jokes in an early-ish Late Night spot. This one’s about meeting his neighbor, a professor of logic at the nearby university.

‘You Think Because I Order a Polish Sausage, I’m Polish?’

Show: Late Night with Conan O’Brien 

Date: October 28, 2003

Macdonald’s second-to-last Late Night appearance — which was followed by a six-year absence — saw him tell a politically incorrect Polish joke. (Which may explain the six-year absence.)

‘Weiner Dog, They Can’t Rip Your Throat Out’

Show: Late Night with Conan O’Brien

Date: October 19, 1993

MacDonald’s first appearance on Late Night with Conan O’Brien came just a month into Conan’s 17-year run on the show. Macdonald only appears as a stand-up and does a set about dogs. It’s funny and fascinating, as both men are clearly green, with nothing to suggest what’s to come, especially since Macdonald wouldn’t reappear for another two years.

‘Well, Anyway, That Was My Christmas Story’

Show: Late Night with Conan O’Brien

Date: January 18, 1996

Macdonald explains why a lottery ticket is the worst gift, then tells a long story about bringing an unhoused man into a diner. The story plays like one of his meandering jokes, yet there’s no punchline. When watched in conjunction with the rest of these appearances, it almost seems like a deconstruction of the formula (but in reality, Macdonald was likely still figuring it out).

‘Lemme Tell You Something About Gay Porn’

Show: Late Night with Conan O’Brien

Date: November 19, 1996

In this one, Macdonald talks about Bob Dole and speaks of the unifying power of gay porn. He also tells a rambling joke about a senile uncle.

‘You Ever Meet My Uncle Phil?’

Show: Late Night with Conan O’Brien

Date: February 21, 1997

Speaking of uncles, Macdonald tells a hilarious joke about his 80-year-old uncle Phil. I won’t ruin it.

‘I Drinks a Bit’

Show: Late Night with Conan O’Brien

Date: September 23, 1999

MacDonld tells a funny, graphic story about going to rehab, which is only enhanced by the presence of three elderly women in the front row.

‘Do You Know Robert Duvall?’

Show: The Tonight Show with Conan O’Brien

Date: August 31, 2009

Poor Thomas Hayden Church never stood a chance. The generally charming lunkhead actor came on during Conan’s brief tenure on The Tonight Show to share slides from his ranch. Macdonald’s constant interruptions and non sequiturs saved the boring segment by visibly frustrating Church, who pathetically tried to one-up Macdonald by poking fun at him and treating him like a moron. But Macdonald always knew precisely what he was doing when interrupting another guest. This time, he was saving the audience from having to hear about Church’s goat-feeding routine.

‘Andy Richter, the Swedish-German’

Show: Conan

Date: May 17, 2011

For his first appearance on Conan’s TBS show, Macdonald told a joke about “Andy Richter, the Swedish-German,” who is used for sexual pleasure by small-town gold prospectors. It’s hilarious.

‘There’s a Shoebox with a Turtle in It’

Show: Late Night with Conan O’Brien

Date: May 7, 1996

One of Macdonald’s best showings is with an overly complicated joke about a drunk guy in a bar and a turtle. 

‘I Was Too Drunk, I Couldn’t Perform with My Prostitute’

Show: Late Night with Conan O’Brien

Date: March 26, 1999

Macdonald tells a joke that is definitely offensive to little people. 

‘That’s a Special Pig’

Show: Late Night with Conan O’Brien

Date: March 21, 1996

The next addition to Macdonald’s menagerie of animal jokes is a pig, as he weaves a joke/tale about a peg-legged pig with a tremendous payoff. 

‘I Had to Have a Huge Shit’

Show: The Tonight Show with Conan O’Brien

Date: June 11, 2009

Like many of these clips, this one is incomplete, but what made its way online is an absolute gem. During Macdonald’s first of three appearances on The Tonight Show with Conan O’Brien, he and fellow guest Jim Gaffigan stuck around on the couch to help Conan tape local promos. Well, Gaffigan helped. As for Macdonald, he obstructed in spectacular fashion. 

‘Useful Porpoise’

Show: Conan

Date: May 21, 2014

On this episode of the TBS show, Macdonald shares the tale of Canadian Frenchman Jacques De Gautier.

‘Doc, She’s Choking’

Show: Conan

Date: October 5, 2016

Very funny and very dirty.

‘Why Would You Become a Cook?’

Show: Late Night with Conan O’Brien 

Date: February 10, 2009

Macdonald’s return after a six-year absence from Late Night, and it was definitely worth the wait. Conan decided to have Macdonald stick around for a Gordon Ramsay cooking segment, where Macdonald’s infantile interrupting and inability to follow directions clearly got under Ramsay’s skin. The high point comes when he asks Ramsay, “Why would you become a cook?” and Ramsay predictably corrects him to say “chef” instead.

‘Also, Rob Schneider’s There’

Show: Conan

Date: November 17, 2016

Macdonald’s final appearance on a Conan show is easily among his best. While his airtime is cut down due to having to share the stage with Adam Sandler, David Spade, Nick Swardsdon and Rob Schneider, Macdonald still manages to get in a good dig at Schneider. The best part of it is that Schneider never sees it coming. The joke begins as another convoluted yarn and ends with a shot between the eyes at Schneider. 

‘Miserable Failure Is Not an Option’

Show: The Tonight Show with Conan O’Brien

Date: January 19, 2010

On one of Conan’s last episodes of The Tonight Show, as NBC was pushing him out to reinstate Jay Leno, Macdonald “stopped by” with a gift basket full of rotten fruit. He explained that he’d bought it seven months earlier when Conan began but forgot to give it to him. He then proceeded to read the card aloud: “Congratulations, Conan, on finally securing your place as permanent host of The Tonight Show. That’s something they can never take away from you. It is perhaps the shrewdest programming decision ever made by the NBC brain trust. Sure, the pressure is on, but if I know you, Conan O’Brien, miserable failure is not an option. You are the new king of late night. Long live the king!”


Show: Late Night with Conan O’Brien

Date: May 15, 1997

When Macdonald passed away, people all over took to the internet to remember his greatest hits. The most oft-cited Conan appearance was this one, where Melrose Place star Courtney Thorne-Smith tried to promote her role in Carrot Top’s Chairman of the Board. When Conan reveals the movie’s title, he dares Macdonald to “do something with that,” causing Macdonald to reply, “I bet the ‘Board’ is spelled ‘B-O-R-E-D,’” which makes everyone, Thorne-Smith included, burst out with laughter. 

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