A large chunk of the internet exists for the lulz. Imagine having to postpone your phone calls for an entire weekend in order to download a 1GB copy of Final Fantasy 7 on a crappy 32 kbps dial-up connection, only to open up the game and realize you got Leisure Suit Larry 6.
I'm pretty sure there were servers out there taking incoming search strings and slapping them on the end of file names. You could search for RANDOM_STRING and find a "britney spears matrix hot babes unsavory search (2)(1)RANDOM_STRING.mov.wmv.exe"
One thing I liked about Napster and the like is that bootlegs and B-sides circulated along with the official releases. I miss not having these on Spotify. Yes, there are official live albums on there. And yes, you can still find these bootlegs elsewhere. But there's enough friction that I rarely do this.
Yeah, Napster's value still hasn't been replaced in full. I remember pulling some obscure song from another endpoint halfway around the planet and then being able to browse their music collection, which turned me on to other cool music. You can kind of do the same thing on spotify by following people and playlists, but it's not the same discovery magic that Napster had, especially for obscure or hyper-local stuff. I'm not enough of a music nerd anymore to care as much these days, but Napster really was the cat's venerable pj's back then.
Like...imagine downloading "The Matrix.avi", and you start playing it, and it turns out it was actually a copy of Fight Club.
WHY!?