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 - chronological order
Directed by: John Hughes
Starring: John Candy, Macaulay Culkin, Gaby Hoffmann, Jean Louisa Kelly
Continuity mistake: In the bowling alley, 'Pal' comes over to speak to Tia. During their conversation, the camera pans to Maisie throwing a bowling ball; however Tia is now sitting alone. Pal has disappeared. (00:40:10)
More quotes from Uncle Buck
Trivia: In the scene in Maizy's class near the beginning of the film, the little girl with long blonde hair sitting at the desk next to Maizy is a young Anna Chlumsky, who went on to be the star of 'My Girl' and 'My Girl 2'.
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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.