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Conan O’Brien: 16 Highlights From His 28-Year Late-Night Run

After 28 remarkable years in showbiz, talk show host Conan O’Brien hangs up his late-night mic on Thursday. The day marks the end of his career as a host who toiled on three different shows on two networks. The last episode of his TBS show Conan, set to air Thursday night will feature Jack Black and other surprise guests.

Back in September 1993, when David Letterman stepped down from the desk of NBC’s “Late Night”, Conan O’Brien was picked as his replacement. Entire America back then had one question: “Who is this guy?”. The man, now a legend, will be the last of a dying breed of TV hosts who stayed as far away as they could from political commentary.

Citing the reason behind the big step, O’Brien, 58, wishes to focus on other projects like a weekly variety show on HBO Max and his podcast, Conan O’Brien Needs A Friend.

Among the countless sketches that premiered on 4,368 episodes, we highlight the 16 most iconic ones that marked the evolution of his late-night run:

1. In the Year 2000
Late Night With Conan O’Brien (1993)

It’s not easy to be right about the future. However, for Andy Ritcherman and Conan O’Brien predicting the future was a cakewalk. A 1993 bit featured Conan and Andy holding flashlights to their faces and predicting how the world would be like in the year 2000. La Bamba’s falsettos were the cherry on the icing.

2. Actual Items
Late Night With Conan O’Brien (1993)

“Actual Items” had Conan and Andy sharing some bizarre real-life newspaper clippings of either news or advertisements that made no sense to this world.

3. Staring Contest
Late Night With Conan O’Brien (1994)

Conan and Andy’s staring contest wasn’t your usual staring contest. Rules were simple, blinking was allowed but breaking concentration wasn’t. Conan would hence have a bunch of artists goofing around his back to distract Andy.

4. Desk Drive
Late Night With Conan O’Brien (1994)

It’s not safe to be on the road when O’Brien is driving. Desk drive was a sketch that featured Conan and Andy driving through the bustling streets of New York City. The duo would take the viewers on a trip that often took wrong turns.

5. Pimpbot 5000
Late Night With Conan O’Brien (1996)

Pimpbot was a hilarious flashy silver robot who had the sensibilities of a 1950s robot with the dynamic flair of a 1970s street pimp. We’ll never know if Conan paid back the loan he took from this silver menace

6. The Masturbating Bear
Late Night With Conan O’Brien (1997)

Listed as one of the most bizarre characters on his show, the masturbating bear surely did bring some discomfort with his arrival. The furry creature would start a task, only to soon drop everything and switch his focus to his crotch.

7. Triumph the Insult Comic Dog
Late Night With Conan O’Brien (1997)

One of the most popular on the show, Triumph the Insult Comic Dog was everyone’s favorite. With a signature cigar fit that would often fall from his mouth, the canine was programmed to roast anyone and everyone that he encountered.

8. Clive Clemmons’ Inappropriate Response Channel
Late Night With Conan O’Brien (1998)

The Inappropriate Response Channel on his show revolved around Conan checking out the many niche cable networks that were featured on his show’s satellite network.

9. Paul Rudd and his never-ending Mac and Me prank
Late Night With Conan O’Brien (2004)

On Paul RUdd’s every visit to Conan’s show for film promotion, he would bring along a clip that he claimed to be from his latest project. However, the clip would be interrupted with an excerpt from Mac and Me, in which a boy in a wheelchair rolls out of control down a hill, off a cliff, and plummets into the water before a silly-looking alien pops up on the screen with an astonished look.

10. The Walker, Texas Ranger lever
Late Night With Conan O’Brien (2004)

When NBC and Universal merged, Conan told the viewers that his low-budgeted show could now show clips of Chuck Norris’ CBS law-enforcement drama for free. The result? Conan pulling a lever to play context-free clips from the show that would leave us in splits.

11. Surviving Jordan Schlansky
Late Night (2001)/ Conan (2008)

Get yourself an enemy but not a friend like Conan. That is something the associate producer of Conan’s show, Jordan Schlansky could tell you. Conan would leave no stone unturned to express his disdain for Jordan.

12. The birth of “Team Coco”
The Tonight Show With Conan O’Brien

Not known to many, Conan O’Brien’s nickname ‘Coco’ was coined by none other than Tom Hanks. During his appearance on the second episode of The Tonight Show With Conan O’Brien, Hanks made the audience chant “Coco! Coco! Coco!” and the name soon took social media by storm.

13. Clueless Gamer
Conan (2012)

The Clueless Gamer segment of the show had Conan and a celebrity guest reviewing an about-to-release game with an actual gamer, producer Aaron Bleyaert. Popping random and irrelevant questions with their disastrous gameplay, Conan and his guest would take reviewing to another comical level.

14. Adventures with Ice Cube and Kevin Hart
Conan (2013)

Ice Cube and Kevin Hart’s appearance on Conan’s show was one of the most remarkable joyride episodes. On their hunt for the “good weed spot”, Hart and Ice Cube hopped onto Conan’s ride who brought along his staffer/student driver Diana Chang. While the trio might not be the best at giving driving instructions, they’re definitely the best at giving gags when together.

15. Sona with the assist
Conan (2013)

This excerpt talked about Conan’s contentious relationship with his trusty assistant Sona Movsesian. She and Conan met with the show’s HR to clear the air between them because of how troublesome things would get at times.

16. Conan Without Borders
Conan (2015)

A widely acclaimed segment of his show, Conan Without Borders was Conan’s journey to different parts of the globe where dove into their local culture and infused it with his trademark humor. Above is an excerpt from his time in Haiti where he delivered a warm speech to Haitians who were angered over Donald Trump’s remarks about their country.


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Written by Muneer

Muneer is an Indian writer at FandomWire who plans to visit all countries in this world to eat the food on their streets. Obsessed with joggers, he sings and plays the strings too.