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He did a couple of times. But his character when playing a criminal was always good at heart. I think he made a point to make the outlaw have a code of ethics so the audience could relate to them on some level. For example, in his last movie The Shootist his character was a gunfighter. But Wayne portrayed him not as a mean man but as a flawed and all too human man.

Other films John Wayne in which played disreputable characters include:

Trouble Along the Way -- corrupt College Football coach

Reap the Wild Wind -- makes money by causing sea wrecks and then "salvaging" the wrecks, little better than a pirate

Pittsburgh -- self-centered industrialist

In all of these films, and in the others that I can recall, Wayne's character has the integrity to recognize that was he is doing is wrong, and to willingly accept the consequences of this wrong. I've seen over 120 films with The Duke, and in none did he play an out and out bad guy.

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14y ago

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