Release Year: 1943
Costume Designer: Walter Plunkett
Who vs. Who: Daniel F. Somers (John Wayne) vs. Jim 'Hunk' Gardner (Albert Dekker)
Flavor Flav once famously said "Fuck John Wayne," but back in the day the movie star would've snapped Flav in half like a twig. He was the Western genre's posterboy, meaning he showed city folk how to look like a cowboy without forcing it. As he tangles with an evil buckeroo during In Old Oklahoma, Wayne's button-down actually gets cleaner as it catches more and more dirt. That's true grit exemplified, partners.