8. Conan Gives Hilton’s Furniture an Advertising Makeover (2000)
This remote piece from 2000 makes the list for sentimental reasons just as much as his comedic content. Two major events of Conan’s professional and personal life are foreshadowed.
First we get a Jay Leno reference in the setup. In the process of explaining how Late Night with Conan O’Brien airs much later in Houston, O’Brien gives his trademark Leno impression. He also says that “whey Jay Leno tells you something, that’s supposed to be a pact.” Unfortunately, that proved to be anything but the truth years later during NBC’s Tonight Show disaster.
But it’s not all bad memories brought up by this piece. It’s also when Conan first met his future wife Liza Powell. At the time of this bit she was working as a copywriter for FCB and clearly caught Conan’s eye. They now have the wonderful story of how a chainsaw-wielding furniture salesman from Texas brought them together.
The clip can certainly stand on its own for comedic value. It is a great example of how O’Brien can play the dumbest man in the room but with a sense of self-confidence that is unshakable. And while Liza and the other FCB staff seem in on the joke, the same can’t be guaranteed for Hilton.
Late night ads for small, local businesses are something that everyone is familiar with and have no doubt laughed about. The genius of Conan is being aware of that and turning it into a ten minute remote that lands among his best.