32 Unforgettable Moments From Late Night With Conan O’Brien

In 2021, Conan O’Brien ended his influential 28-year run as one of the most widely beloved and influential figures of late-night television. While his main claim to fame these days is hosting his podcast, Conan O’Brien Needs a Friend, we still consider him one of the best late-night TV hosts of all time, and his 17 years as the face of NBC’s Late Night is enough proof. Let’s celebrate Conan’s introductory years as an emcee by taking a look back at some of his best moments on Late Night.

Jennifer Garner Tries To Correct Conan’s Grammar

While telling an anecdote from the set of Alias, Jennifer Garner insists that “snuck,” which Conan uses in their conversation, is not a real word and that the correct past tense form of “sneak” is “sneaked.” However, after a break, the host gets out a dictionary to prove that Harvard did teach him the proper spelling after all.

Norm Macdonald Ribs Courtney Thorne Smith

When guest Courtney Thorne Smith talks about her upcoming movie with prop comic Carrot Top, the late Norm Macdonald, while sitting next to her, jokes that the film should be called Box Office Poison. When she mentions the real title, Chairman of the Board, Conan challenges him to make a joke out of that. Without missing a beat, he responds with one of the all-time funniest Norm Macdonald quotes: “I bet ‘board’ is spelled “B-O-R-E-D.”

Jordan Schlansky’s First Appearance 

During the 2008 Writers’ Strike, Conan managed to create content by interviewing staff members, including Jordan Schlanksy. The associate producer’s irreverent personality proved to be such a hit that he would make further appearances on the show in bits that just barely exaggerated his true nature.

Jim Carrey Plays Conan In A Biopic

While promoting one of the best Jim Carrey movies, Man on the Moon — in which he portrays Andy Kaufman — the actor tells Conan that he already went on to play another famous comedian in a movie and has a clip to show. The movie turns out to be about Conan, whom he portrays as self-obsessed and volatile in a pretaped bit that also features Al Roker as one of the best talk show sidekicks, Andy Richter.

Conan Tricks Andy Into Appearing On The Today Show In The Buff

In a classic pre-taped bit, Conan shows Andy where to find NBC’s Turkish spa and adds that clothing is completely off-limits before taking off his robe and shoving him through the door. Andy then discovers that he is really on the set of The Today Show, which is in the middle of taping.

Conan Plays Old Time Baseball

When Conan left Late Night in 2009, he said that one of his favorite things he had ever done on the show, and in his life, was spend the day with a group who plays baseball like it is still the 19th Century. It is clear how much fun he had by how invested in the game he gets, going as far as adopting an era-appropriate mustache and accent and acting confused with an airplane flying above.

Conan And Julia Louis-Dreyfus Steal Tina Fey’s Emmy

When discussing Tina Fey‘s recent Emmy win for her lead performance on 30 Rock, Conan convinces Julia Louis-Dreyfus that she deserved that prize and they leave for a moment to take it from her dressing room. The former SNL cast member appears to let the former Seinfeld cast member know she can keep the award, but requests that Conan return another item he stole from her: her undergarments.

Every Time Paul Rudd Played The Mac & Me Clip

One of the most celebrated traditions in Conan’s career is to see Paul Rudd convince him he is about to see a clip from his latest project, only to show a scene from Mac & Me — an “E.T. rip-off” from 1988. The origin of the prank came from a 2004 episode of Late Night, on which Rudd initially announces he is showing a clip from the series finale of Friends.

A Red Kangaroo Tries To Fight Conan And Jarod Miller

Animal expert and recurring Late Night guest Jarod Miller brings on a variety of animals, but the Red Kangaroo proves to be the star of one episode from 2000. He mentions that, because it is mating season, this is not a very good time for the animal to be brought to a TV set, which explains its erratic and combative behavior.

Triumph Roasts Star Wars Fans

One of the most iconic recurring characters in Conan’s career is Triumph, the Insult Comic Dog, who is voiced by former Late Night and SNL writer Robert Smigel. One of the foul-mouthed Montenegrin Mountain Hound’s funniest remote segments sees him take hilariously cruel shots at some Star Wars movie fans as they wait in line for the Attack of the Clones premiere

A Fire Forces Conan To Film His Show Outside

In 1996, a fire broke out in Rockefeller Center which damaged several studios, including the Late Night set. However, that did not stop Conan from putting on a show from outside the building, which featured guests like Samuel L. Jackson and SNL‘s Chris Kattan.

Jordan Schlansky Quizzes Harrison Ford

Jordan Schlansky appears on a 2008 episode to ask guest Harrison Ford a trivia question about the Indiana Jones movies, specifically about the design of the bullwhip the actor used in Raiders of the Lost Ark. Instead of trying to give an answer, Ford uses an expletive to express the question’s pointlessness as part of a bit that, given the actor’s history with interviews, would not have been too hard to believe.

Conan’s All-Child Audience

In August 1997, Conan did an entire episode of Late Night with an audience comprised entirely of minors. While some of the Max Weinberg 7 use classroom instruments to conduct the theme music, Conan does not do much to help his monologue appeal to the demographic better. He even totes CNN financial consultant Myron Kandel as an especially exciting guest.

Conan And Steve Irwin Stage An Alligator Wrestling Match

In 1995, Conan had the late Steve Irwin on his show where the Crocodile Hunter had Conan help him demonstrate what he does in his profession, but not in the way you might expect. Conan and Irwin end up taking turns wailing on a fake alligator in a kiddie pool.

Conan’s Clay Animation Show

In 2003, NBC aired an episode of Late Night that recreates a taping entirely in claymation. So, if you ever wanted to know what Conan, Johnny Knoxville, the late Richard Lewis, and music icon David Bowie looked like if they were made of clay, it is a must-watch.

The Slipnutz Open For Slipknot

In 2001, Conan did a bit in which, on the same night Slipknot was set to perform, the show also booked The Slipnutz, whose act involves them slipping on nuts and singing about it. Four years later, the three Late Night writers who portray the group appeared at a real Slipknot show as the metal band’s opener as part of a prank that does not receive a favorable reaction from the crowd.

Conan And Andy Appear On Rolanda

In 1996, Late Night did a pre-taped spoofing segments from Rolanda Watts’ talk show about teenagers out of control. Conan appeared on Rolanda to confront Andy about his inappropriate wardrobe choices.

Conan Helps A Local Furniture Store Owner Make A Big-Budget Commercial

As part of a contest prize, Conan took Houston furniture store owner Hilton to major advertising company FCB to get him a local TV ad that would blow his competition out of the water. However, what really makes this remote segment special is that one of the ad employees working on the project, Liza Powell, would become Conan’s wife two years later.

A Fire Alarm Interrupts The Show

Conan has done some crazy bits, but there was nothing staged about this incident from 2007 in which a fire alarm went off on 30 Rock’s fifth floor. Conan, ever the professional, leans into it and decides the entire pause should remain in that night’s taping.

Conan Kills Time By Spinning His Wedding Ring

With no writers to create content for him due to the 2008 strike, Conan lets time pass by spinning his wedding ring on his desk like a top. Unfortunately, no matter how many times he tries, he winds up falling short of beating his previous record of 41 seconds.

Conan’s Boat Show

In June 1995, Conan hosted an episode of Late Night filmed from the Circle Line cruise ship on New York Harbor. Highlights include an introductory musical number by the Circle Line Dancers, a bust of Conan’s head perched on the bow, and Ted Lange reprising his role as Isaac from The Love Boat.

Conan And Harrison Recall Their Awkward First Meeting

During his first interview with Harrison Ford, Conan recalls how he unknowingly allowed an elevator to close on the actor, only realizing who it was as the doors began to shut. They recreate the moment from both of their perspectives for the audience to see by animating elevator doors closing on each of their faces, with Harrison giving his signature angry glare and Conan acting shocked at his mistake.

Chris Farley Jeopardizes His Affair With Adam Sandler

In 1995, while discussing the Tommy Boy star’s love life, Chris Farley attempts to ask out a woman from the audience. However, he is then interrupted by his SNL co-star, Adam Sandler, who claims he told him that they had something special.

Conan Combats A Technical Problem By Dancing

To pass time as a technical arises, Conan decides to erupt into an impromptu dance that quickly goes off the rails. He comes close to disrobing but stops due to the limitations of network TV, even when the audience encourages him to go all the way.

Conan Demonstrates Fake Martial Skills On Jackie Chan

Conan “attacks” guest Jackie Chan with fast hand movements, accompanied by pre-recorded sound effects. The real-life martial artist and actor retaliates by pretending to kick him in the face.

The Men Without Hats Conversation Channel

One recurring segment sees Conan try out some obscure TV stations on NBC’s global satellite feed and one of the funniest examples is the “Men Without Hats Conversation Channel.” It shows clips of a man whose attempts to communicate by singing personalized rewrites of “The Safety Dance” — i.e. “We’ll make toast if you want to…” — ruin his life.

Conan Sues The Audience For Not Laughing

On a 2003 Late Night episode, Conan grows so angry at his audience’s lack of enthusiasm during a bit about funny celebrity mailing addresses that he decides to take them to court. Former SNL writer and cast member-turned-politician Al Franken is brought in as an expert witness, who determines that the audience’s lackluster reaction was justified.

Conan Discovers Late Night Is An FBI Operation

In 1997, Conan points out that his long-lost older brother, Scott, is in the audience, at which point Andy calls for his arrest and admits to the host that he is really FBI agent Nick Cooperman. He then reveals that Late Night and everyone involved with it — including the audience — has been an elaborate ruse to catch Scott, who is a convict on the run. Aside from its obvious humorous tone, the bit is actually a riveting portrait of existential dread.

Conan Calls Out The “Clausty” Bit’s Poor Special Effects

A character called Clausty, the Claustrophobic Coffee Mug, is seen attempting to bust out of a cabinet. Conan sarcastically addresses how the effect is created by simply attaching a stick to the mug and moving it back and forth through a hole in the cabinet that can be seen as clear as day.

Conan’s Skelevision Episode

As a Halloween special, Conan airs an episode that replaces all the humans with skeletons who are puppeteered to recreate the events of a previous taping. Guests include Larry King, Omar Epps, and Bill Hader as Vincent Price.

The Robot On The Toilet Loses Its Head

One of Late Night‘s best bloopers sees writer Brian McCann play a robot programmed to use the toilet, which Conan tries to test for glitches in preparation for Y2K. However, the bit goes off the rails when McCann’s robot helmet falls off, to which he responds with a bow before Andy tries to salvage it by putting the helmet back on for him. Conan agrees that nothing in the sketch could be funnier than what just took place. 

Conan Plays “Suck And Blow” With Rebecca Romijin