Smiley

Then the city was broken up, and all the men of war fled, and went forth out of the city by night by the way of the gate between the two walls, which was by the king’s garden; (now the Chaldeans were by the city round about:) and they went by the way of the plain.

^smiley after "about"^

King James Version of The Bible, Jeremiah 52:7


I guess typed smilies have been around longer than I thought.