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Kilimanjaro Expedition is a sketch from the episode of Monty Python's Flying Circus "The Ant, an Introduction", also appearing in the Monty Python film And Now For Something Completely Different. It has been compared to a comic episode in Franz Kafka's The Castle in which the protagonist, K., is confused by a pair of twins assigned to assist him.
Arthur Wilson (Eric Idle), a young mountaineer, visits the office of Sir George Head, OBE (John Cleese), who is leading an expedition to Mount Kilimanjaro. Head's problem, though, is that he has a bad case of diplopia, and indeed believes there are two Wilsons when he enters the office. He must cover his right eye to confirm Wilson's claim that there's only him. Head begins filling out Wilson's application, though he repeatedly asks both Wilson and the empty chair beside him the same question.
Head then fills him in on the expedition; him and his team plan to climb the two peaks of Kilimanjaro. Wilson claims there's only one, and Head consults a topographical map of Africa with one eye to confirm the claim. Head then explains the expedition is to find any remnants of the previous team, led by his brother. They were trying to build a bridge between the two peaks, which was naturally Head's idea. Wilson then gives his qualifications. When he describes himself as a mountaineer, Head must look the word up in a dictionary (due to his affliction, he reads the definition aloud as "two men skilled in climbing mountains").
Wilson then learns Head also thinks there are two of him as well. Head explains the team's route to Kilimanjaro, but his route mostly consists of a way from Surrey to Rottingdean, with a leap from Rottingdean to Nairobi — Head's map of Britain cuts off there, and is overlying his map of Africa — and then down to Tanzania (all the while Head describes everything in plural, i.e. "Rottingdeans", "main roads near Purbrights"). Wilson inquires about the rest of the team; there are five other members, Head of course thinking each are two brothers (or four brothers in one case, a 'pair of identical twins'). None are mountaineers and none but one speak Swahili. When Wilson asks Head if anyone else speaks Swahili, Head replies: 'I think most of them do down there.'
Their guide, Jimmy Blenkinsop (Graham Chapman) has however worked out a route. He comes to the office, reassures Wilson about Head's double vision, and then shows the route rather physically, acting it out in the office and knocking over numerous items and a bookshelf before wandering out the door still describing the plan. Wilson is now fed up, and leaves the expedition for his lack of confidence. The suddenly visible "other" Arthur Wilson tells "both" clearly visible George Heads that he's still on board for the trip. In the movie version only one George Head is ever seen.