Continuity mistake: When Buck is on the highway driving to the house and trying to remember the kids' names, we see a white 4x4 travelling the same speed as him but several lanes over. When it cuts to a shot of the rear of Buck's car, there is a small sedan now in the left lane beside him that wasn't there before.
Uncle Buck (1989)
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Directed by: John Hughes
Starring: John Candy, Macaulay Culkin, Gaby Hoffmann, Jean Louisa Kelly
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Trivia: The scene where Macaulay Culkin was waiting at the door for the babysitter and imagined the three burglars was the scene that inspired the box-office hit, Home Alone. (01:16:10)
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Answer: It's never explained, but the best guess is the hat was an Ushanka hat which is often associated with Russia. At the time, there was a lot of Soviet Union controversy so being associated with supporting the Soviet Union could have angered many people.