Hahah. My best friend and I found "The Next Degeneration" (these spliced audio clips of Star Trek Next Generation Picard putting the moves on Riker) to be hilarious. My friend showed it to some typical friend of his (likes sports and video games. manager of a Staples.) and he was so pissed off. He said, "why would someone expose a friend to this??". HAHAHAHAHA!!! I still find that story hilarious.
A couple of years ago I heard a bit that consisted of soundbites from the first Star Trek series that were spliced together to make it sound like Kirk and Spock were actually having gay sex ("I think you found the wrong entrance point!").
A friend of mine had recorded it on a mixtape that consisted of other novelty bits, and it was one of several items we had playing during an extended multi-city road trip.*
I can't remember what everyone else in the car thought of it, though. And since this was back in 2001 I'm not sure if anyone still has a copy of it, either.
Yeah, we had that one too. It's still around the internet. Almost nothing gets lost on the internet. I think the one I had also had guys laughing in the background, which was kind of annoying.