John Wayne
Early in his career, 27-year-old John Wayne appeared as "Singin' Sandy Saunders" in Riders of Destiny (1933) and seven more films for Monogram Pictures. Wayne's version of the singing cowboy was much darker than the later ones; his ten-gallon hat was black instead of white and he'd chant about "streets running with blood" and "you'll be drinking your drinks with the dead" as he strode purposefully down the street toward a showdown.
The films were successful and made Wayne a star after several failures, but he refused to renew his contract in 1935, although he did continue making nonsinging Westerns for Monogram's successor, Republic Pictures. Because Wayne could not sing, his filmed songs were dubbed by the son of director Robert N. Bradbury, making the obligatory personal appearances a continuous embarrassment for the young actor. Wayne also emphasized authenticity in his westerns and knew that real cowboys did not sing or wear Singin' Sandy's elaborate costumes.
Read more about this topic: Singing Cowboy
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