From a marketing point-of-view, it's not hard to see why Superman met Annie Oakley. America loves its frontier legends, and the trick shooter, best known for her work with Buffalo Bill's Wild West Show, remained part of popular culture long after her death. The musical Annie Get Your Gun had just started its broadway run when Superman #70 hit the stands, and highly-fictionalized versions of Ms. Oakley would soon appear in a tv series and a comic book.
What reason the story gave for Supes meeting some version of Oakley (who died in 1926), I cannot discover. Comics of the era frequently featured covers that were unconnected to the stories within; the Oakley piece, however, clearly runs in this issue, which is courtesy of Mike's Amazing World of DC Comics.
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