I'm kind of in love, at the moment, with the idea of USB dead drops. This is something that's apparently been going on for quite some time, and there's even a few here in my own city.
Some elements of my fascination with Dead Drops come from the idea of 'you don't know what's in here'. There's sort of a lucky dip aspect to it. The reason behind this fascination is pretty simple - prior to the strong emergence of google, the internet felt uncharted and there was a sense of it being territory to explore. When I entered the internet in 1997 (around the release of Diablo I, as this was the game I played the first night we got online), there weren't very useful search engines (erk, Yahoo), and a lot of navigation around the net was based on the concept of directories. In short - you started at point X (the directory), picked a topic and explored down the links thereof. You wandered.
It was obviously significantly less efficient - finding something you needed could take hours (whereas in the era of mega-sites and infodumps like Wikipedia, IMDB, etc it takes mere seconds) - but there was an enjoyment to that. It's hard to tell whether I genuinely enjoyed those times more, or whether it's simply my nostalgia nerve being gently stroked, but the period of time remains a point of interest for myself.
This period of exploration and random content finds was also shown during the eras of various filesharing systems. SLSK allowed you to actually explore the files a user had on offer - and you could get a sense for that person from what they chose to share. It also had an interesting mentality behind it - in that if they had a few files you wanted, then the rest seemed like a recommendation.
In its earlier days, wikipedia had this sense as well - the phrase 'wiki walk' meant to start at a particular point and then slowly read any linked articles as well. There was a common joke about how every page would eventually take you to the one for Art. TV Tropes also seems to have this particular sense, though I find myself shying away from this approach as it becomes far too immersive as well.
I'm not entirely sure what I really want out of this line of thought - obviously, the internet has grown far beyond the 'exploration' phase and we've had to move onto the time of sharp info requests and info-snacking (or we'd just go insane trying to consume it all). When the cycle of Hunt/Acquire/Sort/Consume becomes shortened drastically into just Sort-Consume (due to Hunt being easier via search engines and Acquire becoming automated via download systems & faster speeds), it's an odd place to be.
You'll notice I didn't link you to tv tropes there. You're welcome