One great thing about Conan O’Brien is that he has embraced absurdity his entire comedy career. Just think: “Mr. Short Term Memory,” a man who forgets everything every few seconds on SNL. Or Lyle Lanley, a sly con man who convinces Springfield to purchase an expensive monorail on The Simpsons. Or the Masturbating Bear, a well… yeah, masturbating bear on Late Night with Conan O’Brien. You see where I’m going with this?
So, it’s no wonder that Late Night with Conan O’Brien (which debuted 21 years ago on September 13) has accumulated an impressive catalog of weirdly brilliant recurring sketches that Late Night, Tonight Show, and TBS-era Conan fans will never forget. Here we take a look at some (I could list hundreds more) of the sketches that highlight just how brilliantly absurd the lanky redhead allows things to get.
12. Pierre Bernard’s Recliner of Rage
Conan struck comedy gold when he gave Late Night graphic designer Pierre Bernard Jr. a platform to express his rage with everything from Stargate to bottle caps, while maintaining a deadpan delivery.
11. If They Mated
Conan used photoshop to combine the most distinguishing features of celebrities faces into a mash up of hideousness. Who knew Conan was the offspring of Kelly Ripa and Clay Aiken?
10. Party Photos
Conan’s photos told the story of the debauchery that went on when him, Max Weinberg, and announcer Joel Godard got together on the weekends. Things typically got pretty weird.
9. Conan Hates My Homeland
This bit became a quick way for Conan and his writers to find out what countries the show aired in by insulting every country that exists. Take that, everyone ever!
8. Movie Casting
Conan has always had a team with a great eye, which is why this sketch works so well. His team would find celebrities, who looked like other celebrities and cast them in a made-for-tv movie. How does George W. Bush played by Ralph Wiggum sound?
7. Celebrity Survey
Using the rule of three, Conan asked three celebs the same question, two of which had normal answers and the third one having a ridiculous answer. Survey says: Nicolas Cage lets his dog pick the movies he stars in.
6. Actual Items
This bit, which appeared in the first episode of Late Night, parodied Leno’s ‘Headlines’, by taking everyday newspaper ads, and embellishing product details in the fine print. Now how is anyone supposed to buy a house without envisioning “The room you will die in.”
5. Via Satellite
A talking head bit featuring such recurring guests as George W. Bush, Geraldo Rivera, and Arnold Schwarzenegger spouting off absolute nonsense.
4. Celebrity Secrets
Celebrities from Gwenyth Paltrow to David Bowie took part in this bit, set in a police interrogation room, where a celebrity revealed ridiculous secrets about themselves. How else would any of us know that Alex Trebek had a “potent potables” problem?
3. Year 2000
This sketch, which continued post-2000, started out with Conan and Andy Richter looking into the future and making absurd predictions based on relevant pop culture, while LaBamba by sang “In the Year 2000” using falsetto between predictions. I don’t want to live in a world where these predictions aren’t true.
2. Triumph the Insult Comic Dog
Another one of Robert Smigel’s brilliant creations, Triumph the Insult Comic Dog tells it straight, whether people like it or not, and has roasted everything from Star Wars fans to Occupy Wall Street protesters.
1. Walker Texas Ranger Lever
Conan was hip to the absurdity of Walker Texas Ranger long before Chuck Norris jokes became a hacky internet fad. In this bit Conan pulled a lever that played a ridiculous clip of Norris typically roundhousing a bad guy into another dimension. The bit really hit its stride when it featured a clip of a young Haley Joel Osment stating that Walker told him he has AIDS.