Editor’s Note: Delving into the archives of pop culture history, “Remember When?” is a CNN Style series offering a nostalgic look at the celebrity outfits that defined their eras.
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Every now and then, a piece of pop culture will capture the perfect storm of talent, story and style to withstand the test of time. One such example is the 1985 comedy-drama “Desperately Seeking Susan,” starring Rosanna Arquette as bored housewife Roberta and Madonna as the titular Susan, an enigmatic downtown punk who captures Roberta’s attention through personal advertisements in a newspaper.
When Madonna was cast, ahead of filming in the summer and early fall of 1984, she was a…