Typographic faces in The Strand magazine, England, March 1909. from yesterdaysprint
Scott E Fahlman suggests a use of :) and :( in September, 1982. This happened on a bulletin board at Carnegie Mellon University in Pittsburgh, USA. It caught on pretty fast, and in November there were already several variations.
What seems to be a smiley from 1648 (top), written by the poet Robert Herrick, is most likely not. The same book contained more smilies (bottom) that indicate that it’s not supposed to be read as an emoticon. See Slate’s article for more examples and information.
Members of the <3 (-: O religion has created the largest ASCII mandala.
the cryptically cute and stoic emoticon religion, <3 (-: O , use emoticons as a surrogate for physically expressing all emotions. they also combine emoticons and ascii art into powerful sigils used in meditation. recently several large international conferences have been convened to stoically share new developments within the emoticonic community. at one of these conferences, members constructed the largest ascii mandala currently in existence.