NBC suggested that Letterman not be mentioned in the inaugural episode on September 13, but O’Brien knew that was absurd. He, his head writer Robert Smigel, and his team found the perfect way to address this head-on. The cold opening found O’Brien walking down the street cheerily, as everyone he encountered greeted him with a similar refrain: “You better be as good as Letterman.” Then O’Brien retreated to his dressing room and—while whistling—prepared a noose to hang himself before a crew member informed him that it was time to go on. That’s how Conan O’Brien introduced himself to the world.
The opening let audiences know what they were in for: silliness with splashes of intellectualism and edginess, plus a final coating of self-deprecation. It was a far cry from Letterman’s beautifully constructed sardonic style or Leno’s more traditional desk jockeying. It was a new show for a new generation.
To mark the show’s 30th anniversary, Vanity Fair spoke to O’Brien and many of those in his orbit about that wild first year.
I’ve long considered Conan a personal and professional inspiration. This fantastic oral history, as compiled by Andrew Buss, truly underlines the special chemistry of the shows first year which launched a 30 year legacy.