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I'm a child of the 80's, so my wheel house is like Caveman, Strange Brew, Weird Science, Police Academy, Red Dawn, Pretty in Pink, Fast Times at ridgemont High, Goonies, etc...so I'm with ya.
Of those choices I would say Caveman and Pretty in Pink would be the only two that fit for me. The other ones I have no embarrassment at all saying I like those movies.
Pretty in Pink is one of the very few movies mentioned in this thread that absolutely qualifies. First, it's a terrible movie, so it qualifies on the "bad movie" dimension. But films like Roadhouse and Bloodsport are also bad but will never, ever get you made fun of among your guy friends at a bar, whereas Pretty in Pink will result in you being mocked for the remainder of your days. Good call.
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