Factual error: In the shot where Uncle Buck is in the living room dancing with that woman, the song "Laugh Laugh" by the Beau Brummels is playing. However, the 45 we see spinning on the turntable is not "Laugh Laugh". It is a 45 on the Uni label, and the Beau Brummels' 45s were on the Autumn label.
Uncle Buck (1989)
1 factual error
Directed by: John Hughes
Starring: John Candy, Macaulay Culkin, Gaby Hoffmann, Jean Louisa Kelly
Continuity mistake: The scene where the elementary school teacher asks his kid what they did that week. After he asks that question and Maizy raises her hand, look at the desk belonging to the girl in the row next to Maizy. It has crayons and other supplies on it. After the teacher calls Maizy's name, the shot goes back to her, showing the girl in the next row's desk completely empty. (00:58:00)
More quotes from Uncle Buck
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.