Conan, Andy, and Me: Remembering Late Night with Conan O'Brien

Late Night with Conan O'Brien first aired on September 13, 1993. I'm not sure when I first tuned in, but it must have been shortly after that, and it hooked me immediately. It appealed to me in ways David Letterman and Jay Leno did not. The dynamic between Andy Richter, Max Weinberg, and Conan, along with the strange skits that felt more like the odd, hallucinatory sketches from The Kids in the Hall than those of his late-night rivals, sucked me in. I raved about it to my friends who were much more interested in David Letterman. Leno was not cool to many of us because his jokes never felt like they were for us. Letterman was hipper because of his biting satire and relatability, while the newcomer Conan was tentative and unsure of himself as a host. His self-deprecating jabs and vulnerability gave him a different type of comedic edge that appealed to the underdog and the also-ran. I started taping my favorite skits and showing them to friends. I have hours of VHS tape of Conan that I used to rewatch until the tracking failed and the audio went out of whack.

The show was ahead of its time for network television and, at first, seemed like it should have been on late-night cable due to the over-the-top skits and the bluntness of the characters. Not surprisingly, due to Conan's inexperience and the strangeness of the material, the show did not find an audience right away and was close to being canceled. In fact, the NBC affiliate near me took it off the air and replaced it with episodes of Star Trek: The Next Generation. I was pissed, but it started becoming popular, and I was soon able to watch it again. Part of the reason that Conan did not hit instantly was because of the show's emphasis on skits and not guest stars. The show also straddled the line between the sophomoric humor of Adam Sandler and Conan's more cerebral material. However, once Robert Smigel and the other writers hit their stride, the show started receiving Emmy nominations. 

Characters like Andy's Little Sister, expertly played by Amy Poehler, the Masturbating Bear, Carl "Oldy Olsen," and Triumph, the Insult Comic Dog were different, yet quite funny for a younger audience that found Letterman pompous and Leno staid. Although they were juvenile, these characters entranced me and started me on a path to learning about other comedic characters and personalities. I soon saw Oldy Olsen in The Wedding Singer and followed Triumph's trips to political conventions, and started paying more attention to the actors and writers involved in the skits. 

Sketches with Andy Richter and Max Weinberg as characters were some of my favorite moments on the show because they pushed boundaries. In one skit, Weinberg pretended to be Bruce Springsteen by putting a handkerchief in his pocket and walking into the room backward to impress groupies who wanted to meet the boss. Another favorite was when Andy Richter and Conan appeared on a daytime talk show in a segment titled "My Sidekick Dresses Too Sexy." Andy enters in a belly shirt and short shorts while Conan plays the straight man who always relies on self-deprecating humor. 

There were many interesting sketches that probably fell flat for many but hit the mark for me because I saw them at the right time in my life. These include a skit where the show's new director is a punk and discusses the changes he will make while Minor Threat plays. Conan's "Happy New Year to the Central Time Zone" was also a favorite because someone finally considered that many of us did not live in New York City. Another classic set of sketches included the super-imposition of lips onto images of choice celebrities, such as Bill Clinton and Keith Richards, who calls Conan "Conesy, Bonesy." 

I just listened to the audiobook version of Live From New York: The Complete, Uncensored History of  Saturday Night Live as Told by its Stars, Writers, and Guests, and it reminded me just how important Late Night with Conan O'Brien was in my formative years. I still follow Conan and his projects, but none resonates in the same way that those early 1990s episodes did. It seemed like the show was speaking to me directly as it appealed to my odd sense of humor and my underdog, teenage self. The way that many in Live From New York discuss how Saturday Night Live affected them makes me realize that Late Night similarly affected me. It helped me feel safer in my own skin while introducing me to a world of comedy I never knew existed.