Conan O’Brien’s 15 Best Late-Night Comedy Bits of All Time

The post Conan O’Brien’s 15 Best Late-Night Comedy Bits of All Time appeared first on Consequence.

Editor’s Note: This article was original published in 2021. It is being re-published today in light of Conan’s 61st birthday (!) and the premiere of his new Max series, Conan O’Brien Must Go.

Over 30 years, Conan O’Brien has entertained us with multiple late-night shows, bringing the laughs through stand-up, elaborate pre-taped segments, and absurd sketch comedy — not to mention his ability to highlight and elevate the talents of Jordan Schlansky, who might just be the most famous associate producer in television.

Here are our 15 favorite Conan bits from over the years, in no particular order.

The Slipnutz Open for Slipknot

Late Night With Conan O’Brien, 03/09/05

Some of the funniest bits on Conan’s late-night programs were based on very simple (and sometimes endearingly stupid) ideas. When Slipknot performed on the show, Conan introduced The Slipnutz, a goofy comedy troupe whose entire act consisted of them singing a silly song and slipping on nuts. But as Conan tends to do, he took it one step further by having The Slipnutz open for Slipknot at an actual concert. The reaction from the sea of metalhead fans is priceless. — Spencer Kaufman

Conan Forces Jordan Schlansky To Clean His Filthy Office

Conan, 01/10/14

Admit it: we all let our workspaces get a little unkempt sometimes. But your office probably isn’t as messy as Conan producer Jordan Schlansky, whose boss described him as a “borderline hoarder” during a 2014 episode. As any gentleman would do, Conan brought in a professional organizer to back him up when confronting Jordan’s sloven habits. After a well-intended roast, the trio got to work for a very satisfying speed cleaning of Jordan’s office. Don’t worry — Jordan’s precious jar of sauerkraut got to stay. — Abby Jones

Conan Catches Jordan Schlansky Coming In Late

Conan, 08/06/13

In what’s probably the best introduction to the Jordan Schlansky Cinematic Universe, Conan gets to the bottom of why his associate producer is forever late on Fridays. While waiting on Jordan, Conan goes through his cluttered office, making fun of everything from the mini pepper grinder on his desk to a box of unopened Star Wars toys. The longer Jordan takes, the more quips Conan has, and they don’t stop once the associate producer finally arrives and shows off even more of his idiosyncrasies. Jordan still works for Conan, so despite his attitude in the clip, they seem to be on good terms to this day. — Annie Black

Steven Yeun & Conan Visit A Korean Spa

Conan, 02/11/15

In 2015, Stephen Yeun was a fan favorite on The Walking Dead, one of the most grueling TV shows of the 2010s. But even his experience fighting zombies on screen couldn’t prepare him for the task of baring it all with Conan at a traditional Korean spa. Together, Stephen and Conan took a dip in a cold bath, sat in a sauna, and received a full-body scrub, all while hilariously in the nude. Thankfully, the duo made some friends (and perhaps a couple of enemies) along the way on their quest for relaxation. — A.J.

Triumph the Insult Comic Dog Insults a Bunch of Star Wars Nerds

Late Night With Conan O’Brien, 05/17/02

We have Conan to thank for the introduction of Triumph the Insult Comic Dog, a hand puppet hilariously voiced by writer Robert Smigel. One of Triumph’s most triumphant moments came at the New York opening of Star Wars: Attack of the Clones in 2002, when he absolutely roasted a bevy of Star Wars geeks with one killer joke after another. Among his best insults was telling an expectant mom, “That’s the last time he’ll ever see female genitalia!” Ouch! — S.K.

Julia Louis-Dreyfus Steals Tina Fey’s Emmy

Late Night With Conan O’Brien, 09/30/08

In one of his usual strokes of creative genius, Conan convinced Julia Louis-Dreyfus to break into Tina Fey’s dressing room to steal her freshly-won Emmy for 30 Rock. In one of the best show-within-a-show-meets-real-life gags ever, Jack McBrayer made an appearance as his beloved 30 Rock character, NBC page Kenneth Parcell. Julia and Conan proceeded to bully him, with Julia delivering a perfectly-timed “THIS IS MY MOTHERF**KING [EMMY]!” and Conan shoving Kenneth into a wall. Comedy gold. — Gab Ginsberg

Paul Rudd Starts a 15-Year-Long Prank with Mac and Me

Late Night With Conan O’Brien, 02/06/04…and countless times since

Paul Rudd perfected the art of the Rick Roll before it was even a thing. During a 2004 appearance on Late Night to promote the highly-anticipated Friends series finale, Rudd told the audience he got a clip from the then-unreleased episode approved to air on the show. It turns out he swapped it for an absurdist scene from the camp classic 1988 movie Mac and Me instead, throwing viewers for a loop, and when the cameras cut back Rudd never breaks character.

What started out as a bizarre and harmless gag soon turned into a 15-year-long routine. Anytime Rudd came on the show to promote a new project, he would slip producers the same Mac and Me clip instead of the actual promotional video that was supposed to air. The tradition wound up happening eight times with everything from The 40-Year-Old Virgin to Ant-Man. Only one director — Judd Apatow, for This Is 40 — banned him from doing the prank, but Rudd still found a way. “I enjoy it because it’s just so dumb and it means nothing,” said Rudd in 2019. “It just now, for lack of a better phrase, has legs.” — Nina Corcoran

Conan Plays Old Timey Baseball

Late Night With Conan O’Brien, 06/25/04

With summer in the air, Conan decided to celebrate the return of baseball season by visiting Old Bethpage Village Restoration — in 1865. The Long Island town takes historical re-enactments to Olympic levels by playing vintage “base ball,” era-appropriate dialogue and costumes and all. Conan got playful with the dialect (“Some of the worst apple hurling and stick mashing I’ve seen!”) and spendt most of the time flirting with a shy local girl whose husband was off fighting in World War I. Despite all the mockery, the host looked pretty period accurate when he donned mutton chops and a striped hat to take to the mound himself in what will eternally be one of his most classic remote bits. — Ben Kaye

Conan Gives Staff Performance Reviews

Conan, 05/21/15

In one of his most hysterical workplace sketches, Conan conducted staff performance reviews with various production crew around the “Conaco” office. The sketch saw Conan embark on a tear throughout the office, throwing chairs, knocking over coffee cups, and playfully intimidating his employees during interviews. The highlight: when asking his employees who they thought should be fired, each of them answered, without missing a beat, that it had to be associate producer Jordan Schlansky. — Paolo Ragusa

Jon Stewart & Stephen Colbert Crash Conan NYC

Conan, 11/03/11

There’s a lot of late-night shows to keep up with out there, so much so that even their hosts are susceptible to mixing up schedules. During an epic 2011 episode when Conan had a brief residency back in New York City, Conan noticed one Jon Stewart sitting in the crowd like an ordinary audience member. However, when the Daily Show host suddenly realized he was late for work, he sprinted out, leaving his seat open for a very special standby audience member. Wait…what time does The Colbert Report come on again? — A.J.

Conan Hunts Down His Assistant’s Stolen “Gigolos” Mug

Conan, 06/27/13

As the title suggests, Conan once wasted time, money and other resources on a lengthy mission to find his longtime assistant’s missing mug. Likely a piece of promo swag, the mug featured the logo from the Showtime reality series Gigolos on one side, and the words “Working Stiff” on the other. The host gleefully traipsed through the Conan offices to try to figure out who took the mug, taking on the challenge because he found himself to be, in his words, a “spiritual leader” for the staff. It’s one of the best peeks behind the curtain of what it must be like to work for Conan, which seems to be as chaotic as you’d expect. — A.B.

Conan Attacks Jackie Chan

Late Night with Conan O’Brien, 08/15/96

Jackie Chan appeared on Late Night just a few years before Rush Hour made him a Hollywood star. Best known at the time for doing all of his death-defying stunts, the martial arts superstar shared the story of falling 25 feet from a castle to his near death. After expressing relief at Chan’s recovery, Conan proceeded to boast about his own skills as “an incredible martial artist.” As proof, he caught Jackie off-guard with a series of movie punches and was met with a high kick in return. Let’s call it a tie. — Eddie Fu

Really Tall Dachshund

Late Night with Conan O’Brien, 10/11/07

There’s a lot of weird collegiate sport mascots out there, but none of them could top the new mascots imagined by Conan and his team. In 2007, while introducing a few never-before-seen mascots, Conan debuted the Illinois State Really Tall Dachshund. A dachshund the height of a slightly-short human is then wheeled across the stage in celebration. “To be honest…the dog is real, but the legs are fake,” Conan admitted, much to the dismay of house band member Richie “LaBamba” Rosenberg. The legs might be fake, but our love for the dachshund isn’t. — A.J.

Cactus Chef

Late Night With Conan O’Brien, 01/23/2004

Over the years, Conan has delivered a nonstop parade of highbrow, thought-provoking late night comedy that never, ever ventured into the arbitrary or absurd. And forget about visual gags — Conan would never. Isn’t that right, Cactus Chef playing Billy Joel’s “We Didn’t Start the Fire” on a flute? — G.G.

Ice Cube, Kevin Hart And Conan Help A Student Driver

Conan, 01/05/16

Reprising a bit from 2014, Ice Cube and Kevin Hart hopped back in the car with Conan to promote their film Ride Along 2. Only instead of a Lyft, this time they were taken around by a student driver who happened to be Conan staffer Diana Chang. They all attempt to “help” the nascent motorist, teaching her how to throw pennies at aggressive drivers and search for drugs on the road. The advice isn’t as sound as the odd chemistry between the diverse quartet, which was so undeniable the bit hit 26 million YouTube views in its first three weeks, becoming Team Coco’s most-watched clip ever at the time. While it’s a bummer we never got to see that piñata full of weed cracked open, we did get to learn that Tupac always wore his seatbelt. — B.K

Honorable Mention:

Conan O’Brien’s 15 Best Late-Night Comedy Bits of All Time
Consequence Staff

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