NOT TYPED BY ME, SOURCE BELOW!!Source
The origin of LOLLOL was first coined on a BBS called Viewline in Calgary, Alberta, Canada, in the early-to-mid-80s. A friend of mine who went by Sprout (and I believe he still does) had said something so funny in the teleconference room that I found myself truly laughing out loud, echoing off the walls of my kitchen. That's when "LOL" was first used.
We of course had ways of portraying amusement in chat rooms before that (>grin< >laugh< *smile*) and the gamut of smiley faces, but I felt that none of them really got across the fact that the other person just made you feel foolish by laughing out loud in a room all by yourself (or worse, with other family members in another room, thinking you quite odd!)
The use of the phrase LOL spread quickly around Viewline, but it wasn't until a bunch of us got free GEnie accounts that it really became popular.
GEnie, back then, was one of the big online services (with Compuserve and Prodigy), and the hundreds of chatrooms included trivia rooms (run by script bots -- quite fancy at the time!) A bunch of us Viewliners found these rooms and, of course, our jargon mixed with the regulars of GEnie. (One thing that I took from there, and still use today, is "my" smiley -- *:^) )
Of course, LOL was introduce to this new group, who took to it quickly; I always emphasized (and still do) that it was meant to be used *only* if you truly Laughed Out Loud... a smirk, smile or giggle just didn't cut it. These GEnie users soon started mutating it: Rolling On Floor Laughing was borne by the GEnie people.
Today, of course, we see many variations, and I'm amazed daily whenever I see "LOL" appear in obscure places. The "true" use of LOL has been tainted; people use it in the same way that *grin* or "hahahaha" might, but I guess this is the evolution of words and language. I admit that every so often I try to explain to people that LOL has a specific meaning or usage, but most scoff when I explain the origin.
If I had any idea that such a thing would spread, I would have saved the original conversation that led to the acronym's inception. Alas, I don't even recall what was so funny! While I can picture in my mind where I was when it happened, I can't narrow the time down any further.
I don't expect you to believe this, really, as so many others don't. Still, it ought to be written out so there's at least a record of it somewhere on the Internet.
-- Wayne Pearson
Got bored and decided to look up the origins of LOL... was surprised by how old it actually is...