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If Harold and Maude qualifies as obscure then
Blue Velvet deserves a mention as well. I realize it was relatively big in its day and made a lot of critics top movies of the 1980's list, but I occasionally throw some pop culture trivia in on rounds with my medical students/residents and am constantly surprised at how many of them have never heard of it.
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If there was ever a movie that everyone seemed to talk about back then and now nobody seems to mention it then Blue Velvet hits it. Dennis Hopper is the scary creep in this one so he really didn't have to act much.
~ Rick