When I was young, my family really enjoyed Pirates of Penzance. We'd watch this movie over and over, and often we'd refer back to it. One day, I realized I find a re-interpretation of it very funny. Have Pantera do the Pirate King song. Get a rapper to do the Major General's song. Maybe do a techno-remix with that "Hail Poetry" song.
I'm pretty sure this would set me, and perhaps a handful of others laughing on the floor. I say a handful because there ain't too many people who would get all the cultural references. I could maximize my chances by getting an Elvis impersonator to sing the Pirate King song, but the target audience would still be small because you'd have to enjoy both Elvis and Gilbert&Sullivan. Tiny audience indeed.
And if you weren't part of that tiny group?
Well, watch Choosing with Friends. I just know this is really funny, but I don't know the references. So, unless you have the backstory, you'll feel just like you would if you saw my remake of Pirates of Penzance. There are even parts that are funny despite the lack of reference.