1)Watch the part of the movie where Christian(Jack Kelly) is riding the horse. Notice how is hat flys off, and look a second later when he slows down and the quickly cut, you'll notice how the hat magically appeared back on his head.
Actually, according to the production notes for newsies, the sudden appearance of the hat symbolizes the transition from the city to Santa Fe...not bad editing, just plain directing for sake of symbolism.
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That was put in there on purpose to symbolize Jack mentally changing New York into Santa Fe. It was supposed to be a dreamlike scene but it didn't work very well
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