Reference humor is very much like the weather in Milwaukee, Wisconsin. It waltzes capriciously from one extreme to another, it knows no historical precedent. There's no formula to predict it.
I see movies constantly, watch my share of television. I keep abreast of things on the internet, which itself is a more insular place than it seems like from the inside. But there's no way of knowing, even given a crowd's median age, wardrobe, or the venue they inhabit, what avenues of mass media they'll follow you down on any given night.
Case in point- I have a joke, really the only survivor from my early days, which prominently involves Wham! that never seems to be too old for anyone- 80's references in general seem an easier bet than nearly any other decade, seemingly an entire ten years laced with a perfect mix of irony and nostalgia. I was born in 1984 myself, I remember absolutely none of it, pop-culture-wise.
I've worked in libraries and stayed tuned into to bestselling fiction for most of my adult life, thus I have a Nicholas Sparks joke that can be very hit or miss. Sometimes, in the right crowd, I replace it with a Twilight joke which is more universal (but the punchline itself is less biting. It needs work.).
Movies I reference constantly, but even there, even the hugest movies aren't always familiar ground. I had an Avatar joke that never really caught on for me- I think it might be because, despite the big numbers, the majority of people saw it once and moved on with our lives. I do a somewhat involved bit about The Matrix (it's about the déjà vu cat) that does pretty well- because even though it was an R-rated release over a decade ago, everyone's seen it more than twice by now.
It's a challenge that I relish- it makes consuming new art and media exciting. Even if I see a film and find it terrible, it still means I've punched a lottery ticket for my favorite drawing anywhere.
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