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The sketch was invented prior to the actual year 2000, but the show's writers decided to keep the named year the same even after the passing of the titular year, in a sort of ironic twist.However, when the sketch was revived on The Tonight Show with Conan O'Brien, Richter heaped ridicule upon O'Brien for failing to update the name of the skit nine years after the year 2000 had passed.Conan reads a question and then recites the answer that each of three celebrities gave.The answers of the first two celebrities are ordinary "straight" answers. Simpson wrote: "Murder O'Clock." A reply where Paris Hilton is the final respondent to a question has been used in every segment for at least the last four years, usually about her promiscuous dating habits.
The sketch is typically performed with Richter participating, but after Richter left Late Night, the celebrity guest would participate (when Richter was scheduled as a guest, he would again take part).The humor is in how similar the two photos are despite how vastly different the two people/things pictured are or vice versa, with Conan often commenting on how great the casting is. Bush being played by Ralph Wiggum, Patrick Star, or a deer in the headlights, Joe Biden being played by Bob Barker, Hillary Clinton being played by Chucky, Condoleezza Rice being played by Snoop Dogg, Donald Rumsfeld being played by Skeletor, and Dick Cheney being played by The Penguin. As Conan speaks on a recent news story dealing with race, the camera cuts to bassist Mike Merritt, as the audience hears his inner thoughts regarding Conan's lack of knowledge on racial issues and his attempt at "trying to be black." He also makes note of the scant number of black people in the studio, which usually includes only him and an audience member, or crew member, who is either hired for the show or whose skin is heavily made up to look tan.