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20. 1961: Shirley Jones
In 1961, Shirley Jones won the Best Supporting Actress award for her portrayal of a fallen woman in Elmer Gantry and came to the red carpet decked out in a glittering gold dress. The champagne tulle gown was topped off with a cropped bolero jacket, adding more shimmer to the look. 

"I guess it pays to be bad on the screen," she cheekily told reporters that night. Jones was known as a musical comedy heroine, and her switch to a fallen woman was a shocking one to viewers. It was also hard to convince the producers of the film to give her the role. 

Before then, Jones had a sagging career and had a tendency to appear in musical flops. Her role in Elmer Gantry helped put her back on the map and distance herself from her pigeonholed ingénue character. While she might have had to dress scandalous during her audition, Jones cleaned up for the red carpet.