Inspired by a discussion on the Something Awful Forums, I remembered the time I spent using AOL in middle school. There were these programs ("proggies") that would hook into the AOL software and allow you to do special things, like easily type using color-faded text or extended ASCII characters. I had one of these called FateX Ultra.
My favorite function was that you could host these little chat room games, like the "FateX Ultra Scrambler Bot". You'd give the program a word and it would automatically "chat" for you and set up this game where it displays the word scrambled, and whoever typed in the unscrambled version first would get a point, and every so often it would print out a scoreboard of how everyone was doing. And there were chat rooms devoted entirely to these games. It was a pretty big deal at the time for a 7th grader.
Then there were the warez bots. These things were really fantastic, and getting warez through them was surprisingly easy for the time. You'd go into a private chat room (the AOL police wouldn't actively monitor them) named whatever was cool at the time, with some digit after it, usually 1 through 10, since there was a maximum capacity. For example, you'd hear from some of your l33t friends that the new rooms were called "zeraw" (warez backwards, since "warez" names were banned), so you'd try like "zeraw4" or "zeraw6" until you found one that wasn't full.
Then you'd find out who was hosting by looking to see who people were directing requests towards. Let's call them "server". So you'd type something like this:
/server SEND LIST
Then magically, within minutes, you'd have an email containing a numbered list with everything that the server person had. Let's say you wanted "#129: [MP3] Counting Crows - Mr. Jones.mp3":
/server SEND 129
And once you reached the front of the line (anywhere from minutes to hours), you'd have that message in your mailbox. And you'd spend some absurd amount of time downloading it over your 28.8 modem (I was cool, I had a 33.6).
You could even search the list:
/server FIND Counting Crows
That's some incredible functionality for 1995. Add a global search and you have Napster.