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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.
He would sign off by calling Conan a "pasty-faced pumpkin head", just before Conan finishes his speech by saying, "...because we're all part of this beautiful mosaic that is mankind", while believing that the audience is applauding for him.
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 renamed "In the Year 3000", with the black robe (referred to as a 'ratty smock' by Richter) being replaced with a more futuristic-looking outfit consisting of a large metallic collar with a series of blinking lights, which Conan said were very expensive to make and Andy said smelled bad.
Appearing on Tonight June 3, 2009, it was the first Late Night sketch to be carried over to The Tonight Show.
For example, the winner of "Best Foreign Language Audience Member" was shown with a large superimposed moustache and sombrero, and the "Audience Member Who Smells the Most Like Fresh Salmon" was attacked by a man in a bear costume.Awards show intermission segments (red carpet, how the award is built, etc.) are also parodied.Reintroduced on Tonight June 16, 2009, and later reintroduced again on Conan on June 21, 2011." During an "In the Year 2000" sketch, O'Brien, Andy/Guest, as well as band member Richie "La Bamba" Rosenberg, each wears a black robe, futuristic-looking collar and hold a lit flashlight to their face.Between La Bamba's high falsetto wails of "In the year 2000...", O'Brien and Andy/Guest alternate delivering jokes, often based on current events, in the form of humorous predictions of what will happen in the year 2000.
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The third is the gag answer and often relates to something unseemly about the celebrity. To the question: "My favorite time of day is..." Evangeline Lilly wrote: "Dawn." Matt Lauer wrote "Twilight". O'Brien and bandleader Max Weinberg have been used as well, with answers that perceive O'Brien as a loser and Max as a pervert.