Andy Richter has been so closely associated with Conan O’Brien for so many years that sometimes we forget that he actually stepped away from his role as O’Brien’s sidekick for nearly a decade. Back in 2000, after serving as sidekick for seven years on Late Night with Conan O’Brien, Richter departed to purse roles in film and television. His time away was a mixed bag — he starred in three television series, two of which were beloved, but all three were cancelled fairly quickly. Richter returned to his job as sidekick in 2009 when Conan (briefly) took over The Tonight Show.
In either respect, ahead of Richter’s departure in 2000, Jack Black appeared on Late Night with Conan for the first time. When he was on, he auditioned to replace Richter in a bit that, nearly 20 years later, Black would describe on Conan’s podcast, Conan O’Brien Needs a Friend, as the “greatest thing I’ve ever done,” and, according to Conan, “one of the funniest things” he’s ever had on his show.
Black did note, however, that he “felt a little bit bad, because I was enjoying it so much and Andy felt a little bit embarrassed that I was pointing so much attention at his impending departure and relishing at how much better I would be at sidekicking.”
It really is a brilliant bit, so good in fact that Team Coco re-uploaded the bit onto YouTube after the podcast aired, in case you needed to get Jack Black’s sidekick song stuck in your head again.