Well, first is 'Slenderman'. It has been so popular that it has even spawned movies. The idea of a tall, thin figure lurking in the woods is terrifying. 'Jeff the Killer' is really scary with his grotesque appearance. 'Ben Drowned' makes video games seem like a gateway to the supernatural. 'Eyeless Jack' gives a sense of dread as he hunts for organs. And 'The Rake' is known for its sudden and violent attacks. These top 5 creepypasta stories have contributed a great deal to the horror genre in their own unique ways.
There's no precise count. Creepypasta is a genre that's very popular and evolving, so the number of stories is ever-growing and can't be accurately quantified.
I'm not entirely sure of the specific '1999 creepypasta' story in full detail. But generally, creepypastas often involve elements of horror, mystery and the uncanny. It might be about some strange events that occurred in 1999, perhaps involving supernatural entities or disturbing situations.