Following up on the announcement of the smiley emoticon's 25th birthday is an exploration of its prehistory. LanguageLog delves into earlier typographical shapes for emotions, touching on PLATO-era emoticons, a 1967 Reader's Digest letter, and even Ambrose Bierce. Not to mention Vladimir Nabokov:
Nabokov: 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.
(via Cranky Professor)