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Not counting John Bernard Books, did Wayne ever play an outlaw again after this movie?

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He played a gunfighter a couple times like in The Sons Of Katie Elder. But he's such a nice guy that you don't really think about what hired guns did for a living. I think there was a couple other movies where he was a hired gun too. He always played the good guy even if he was bad. Like in this one....Do you but for one second that any of those three were desperadoes? They were the nicest, most thoughtful, and polite robbers ever.

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