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No- he was an entirely fictional character played by Clint Eastwood in the famous 1976 Western, he never existed in real life.

In any case, the character of Josey Wales was more of a 'lone gun hero'- he was essentially a good guy, whereas Jesse James and his like were villianous criminal thugs.

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Q: Was Josey Wales a real outlaw like Jesse James?
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Was the movie outlaw Josey Wales based on a real person?

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How many times does josey wales say 'reckon so'?

In the movie "The Outlaw Josey Wales," the character Josey Wales says "reckon so" a total of 8 times. This catchphrase is often used by Wales to express agreement or acknowledgment in a casual manner. The repetition of this phrase throughout the film has become a memorable aspect of Josey Wales' character.