In Honor Of His 20th Anniversary On TV, Here’s Conan O’Brien’s Very First ‘Late Night’ Monologue

Twenty years ago today, September 13, 1993, a tall, visibly nervous young comedy writer named Conan O’Brien made his debut on NBC’s Late Night, taking over for the recently departed David Letterman. Much has transpired since then. There have been legendary sketches and characters. There have been hilarious, inspired interview segments. There has been controversy (oh, there has been controversy), the end result of which was him leaving his new gig at The Tonight Show after less than a year, touring the country and performing in front of thousands of massively devoted fans, and starting a whole new show on a whole new network. You may have heard about that last part. It was on the news.

All of which makes the very first monologue from his 1993 debut even more fun to watch. For the generation of viewers who were too young to appreciate Letterman’s groundbreaking early work but still remember the pre-DVR, pre-YouTube days when you had to actually, like, stay up if you wanted to catch all the funny parts of your favorite late night show, Conan was our dude. At the risk of getting too sentimental about it, we kind of grew up with him. That’s probably why so many of us got so invested in the Great Late Night War of 2009. At the same time he was getting hosed by short-sighted, bean-counting decisions made by a huge, mostly faceless corporation, we were going through the same thing on a much larger level as the economy and housing market fell to pieces around us. We were him, he was us, Team Coco, etc.

So you look back now and watch this monologue and think, “Wow, Conan was so much younger and more awkward back then,” but then you look in the mirror and you realize those same twenty years hit you, too. Probably a lot harder, seeing as Conan still has most of his signature orange locks. It’s a lot to wrap your head around if you stop and mull it over for a few minutes. And it’s really a lot when you realize that, yes, you are getting a little sentimental, and the thing you’re getting a little sentimental about prominently featured a giant masturbating bear and a cigar-chomping canine insult comic. TV is weird.