Gentlemen Prefer Blondes (1953)
Whether or not it is true as a generality that gentlemen prefer blondes, I'd be hard pressed to believe that many men come out of watching this film preferring Lorelei (Marilyn Monroe). That isn't to speak ill of Monroe, but going up against Jane Russell here as Dorothy, especially given how the characters are constructed, is a pretty tall task. I don't know that this film is particularly memorable as a musical (though Diamonds Are A Girl's Best Friend has obviously achieved classic status), but as a screw-ball comedy it is a resounding success. Given how much plotting occurs on this boat trip to France, one expects the traveled around the globe en route by accident.
One of the most enjoyable aspects of cinema of the era was the creativity that screenwriters had to employ to make dirty jokes without using the dirty words. It is all tackled at the level of innuendo and subtext. While Lorelei plays the prim and proper gal to woo classy gentlemen, Dorothy has a more hedonistic approach to pursuing pleasure. Even as they play different types, they are both entering the realm of taboo. It feels very progressive for its time in its gender commentary on the gold digger type, which certainly has a much more negative connotation than the shallow rich man seeking a trophy wife. This commentary that hides silently beneath the surface for much of the film breaks through with a boom at the end in pretty satisfying fashion. This is definitely an early candidate for my 2017 Discoveries list.