5. MARY STUART MASTERSON AS DANNI IN HEAVEN HELP US AND WATTS IN SOME KIND OF WONDERFUL
Danni in the 1960s-era Catholic school comedy Heaven Help Us would surely have been too cool for me in the real world, but the tomboy drummer Watts was a perfect fantasy: the groovy gal pal who’s been secretly pining for you all along -- then, when you finally catch wise, she’s dressed in a sleek, Goth-y chauffeur’s uniform. Tellingly, in John Hughes’ gender-flipped version of the same story (Pretty In Pink), Jon Cryer’s groovy guy pal, Duckie secretly pines for Molly Ringwald’s Andie, but then has to just suck it while she runs off with...yes, another popular hunk.
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