Note: Before you ask why Triumph isn’t on the list, NBC actually relented on that one.
If They Mated
It’s not a particularly complicated idea: Take two celebrities who are rumored to be dating, mash up their photos, and broadcast the hideous result. Usually, there would be a twist at the end where two celebrities would mashup into another one (in one segment, Barry Bonds and Martha Stewart were smushed together to create Omarosa from The Apprentice). This bit worked for years, and it was a flagship segment of Conan’s original Late Night show.
The Masturbating Bear
Proof that “Sabre Dance” can make anything funnier. As we see in the above clip, the bear did make one appearance on TBS (maybe they worked out a deal with NBC to let it slide one time), but we haven’t seen him since, and I, for one, miss him every day.
What In The World
It was a simple, yet brilliant premise. Start out with a heavily magnified image, and gradually reveal a bit more. The final image is something hilarious, disturbing, or both. But what really made this bit so great was the jingle, where a “boing”-type noise was followed by what in the world??!!. Conan would frequently play the jingle multiple times throughout the segment, and it would only get funnier each time.