There is a lot that is unique about Conan, but some notable aspects of his career are his longevity and global reach. I don’t think that’s a coincidence. He’s Harvard educated, knows his history, wrote on The Simpsons, stumbled into Late Night, and has been in the game for a long time and he keeps going, growing, and expanding. From Korea to podcasts, he’s a case study of someone who made a career of silliness.

Play and silliness is universal. You might call it corny, hacky, or lame. But he taps into the universal silliness that’s cross-cultural and perhaps cross-historical. His vaudeville-like physical humor is childlike and pure. However, he is witty and smart. He’s a professional who works hard and plays harder. He is sarcastic and he has a jaded, dark side to him. He knows all the tools of a good stand-up comedian in virtue of his vast experience. Yet what is remarkable about Conan is his willingness to be silly.

Silliness can be thought of as intentionally looking like a fool. We all do it from a young age and it can be seen among other higher-order primates. It’s playing a role, acting stupid, or being the outlandish clown. It displays an invitation to play and jest with others, and it’s the most basic form of interpersonal entertainment. Silliness can function as a signal to others that you aren’t looking to be combative, you want to neutralize the situation, and you want to engage in play. It’s a form of conflict resolution and social bonding, but it can also be inappropriate in certain social circumstances. For instance, it might be a faux pas to be overly silly at a funeral because the sacred and the solemn should not be undercut by the silly.

Some people might not find silliness funny per se. However, arguably all humor is an evolution of this primitive notion of silliness and play. We might look for more sophisticated forms of humor in the form of wit, wordplay, or deep observations; however, a carefully constructed joke is still a form of silliness. The silliness might deal with topics of the absurd and the ironic, but it still points out the silliness.

What is notable about Conan’s silliness is that it is mainly self-directed, thus, self-deprecating. Contrast this with the “cool” stand-up comedian that takes themselves too seriously to be self-deprecating: there’s a pretense and superiority that is at the opposite end of silliness — such people seem to be communicating socially exclusionary behavior and keeps others at arm’s length. Silliness brings people in. It brings everybody in to share in the joke of his foolish clown act.