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.