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Sergio Leone directed two similarly titled films:

What is the connection between the films? Is there a reason the film titles are so similar? Is there an in-universe connection? Did Sergio Leone ever mention a reason for the similar titles? Are they meant to be part of an anthology? (I realize that's a lot of questions so I've emboldened the root question I'm asking.)

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    What I do think to have heard is that he actually wanted to do America first and has always wanted to do that project. But before going about this he was convinced that he "owed" Hollywood a proper Western or something like that. For whatever that's worth for answering the actual question. – Napoleon Wilson Oct 29 '18 at 19:17
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    Not by Leone but there's whole lot of movies named 'Once upon a time...' , see here in imdb – Vishwa Oct 30 '18 at 3:48
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    Leone read Goldberg's book while filming 'Once Upon a Time in the West'. When the two finally got together he asked Goldberg to help him better understand America. This became Leone's 'Once Upon A Time in America'. So the connection, at least in this regard, is through the discussions and collaboration between the two over several decades beginning with one film (about the American West) and ending with the other (American gangsters). This is the connection I see from having read Frayling's book. There maybe others. – wcullen Oct 31 '18 at 5:48
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    @wcullen seems like you could probably flesh that out into a decent answer. – sanpaco Oct 31 '18 at 6:00
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    I'd definitely be interested to hear more about what the book says about this. – sanpaco Oct 31 '18 at 6:08
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After the Dollars trilogy Leone wanted to do what eventually became known as the "America Trilogy" Once Upon A Time in the West, Once Upon a Time in the Revolution (also known as Die You Sucker), and Once Upon a Time in America are all part of that trilogy.

https://www.imdb.com/title/tt0064116/trivia?ref_=tt_trv_trv

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Your core question was already answered by @Rosie. But i will take a few lines to reply to

Is there a reason the film titles are so similar?

The phrase Once upon a time ... is a very common pattern when starting a fairy tale. So by naming his movie with this prefix, Sergio Leone emphasizes that he is telling a story in the sense of a fairy tale that you might have been read to as a kid. Just in a different format and with horses and guns instead of kings and dwarves.

It might also be worth noting that the English title might not have been the original name, but the Italian one.

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