For me, a simple deciding factor is "If you didn't know this was from a contest, would it still make you think about the theme?" I give Hal credit for the nice chestnut-colored photography, and I'm always pro-Milena, but it was really R&H Bob who got this rolling. As ever when a contest gets good, the voting can be agonizing. For a while there I saw this contest as Leon's -- sure, he sort of cheated, but he fulfilled the idea. My main quibble is the Taft reference -- after all, you also seem to have TR in the background, and I like to think that TR would have looked at Heather and exclaimed "BULLY!"
A bit sad, but understandable, that 3der didn't make it -- yes, technically prehistoric, but it WAS really a Sixties movie. (In just a couple more decades the original "One Million BC" could fit this.) For d-jay's pic I offer the caption "Model Boo-T."
Beyond all that, the next consideration was "Does it make you pop?" I do consider it a damn shame that WebMuse didn't wise up last year, because I still vividly recall his Bazoom County Bathing Beauty Contest which would have been right up this alley, and without abusing anyone under 18 either. More fool him. At any rate -- this was another intriguing contest.