Back in 1959, critics were already asking if John Wayne was too old to be playing gunslinger leads.

Rio Bravo was released that year and the romantic age gap between the 51-year-old and his 27-year-old co-star Angie Dickinson had received negative reactions in reviews.

Nevertheless, the Hollywood star found ways to play older cowboys over the next couple of decades, even as his health began to decline dramatically.

Wayne was 65-years-old when he shot one of his last Westerns, 1973’s Cahill US…