'The Duke' made so many flicks. Most don't hold up very well, but many are indisputable classics (The Searchers, True Grit - Being remade right now by the Coen brothers). However, he had some hilariously politically incorrect opinions on race.
“I believe in white supremacy until the blacks are educated to a point of responsibility.” - John Wayne in a 1971 Playboy interview
The guy pretended to shoot thousands of 'dirty injuns' in the name of white manifest destiny, so I'm sure it skewed his views on things just a bit.
I would say Steve McQueen would be the hands down coolest, but he just didn't make enough flicks (however awesome he was in each and every one of them).
All-time coolest comes down to Paul Newman, Nicholson, and Squintin' Clint.
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