The reaction to something that at first appears funny, then reveals itself to also be very sad, or vise versa (e.g. The Darwin Awards)
Can also refer to a reaction to something that is innately funny AND sad (e.g. Forever Alone guy)
Hey did you see those midget clowns punching each other before?
yeah that was hilarious, until one of them died. that made me lolcry
Hey Bill, your life is pretty pathetic! I bet you'll lolcry at this new Forever Alone meme I found!
Basically when you do not know whether you should laugh or cry, so you LOLCRY.
Colin Farrell is staring in the remake of Total Recall?