Way back in the late 1990s, Dave Barry posted a highly inventive list of emoticons. Some of my favorites include
- :-0WW (person vomiting a series of Slim Jims)
- :V:-| (person who cannot figure out why nobody wants to talk to him or her, little suspecting that there is an alligator on his or her head)
You should go visit this page; it is delightfully Web 0.5.
Even older than things from 1997 (I know!) are these images from 1881:
And finally, Nabokov pondered the use of punctuation as image as well:
In a New York Times interview in April 1969, Alden Whitman asked writer Vladimir Nabokov: “How do you rank yourself among writers (living) and of the immediate past?” Nabokov answered: “I often think there should exist a special typographical sign for a smile – some sort of concave mark, a supine round bracket, which I would now like to trace in reply to your question.”