



IBM building, Honolulu. By Vladimir Ossipoff, 1962





9/11-themed art works by Douglas Coupland, on display at the Daniel Faria Gallery.
h/t: the Guardian


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.
There are many older examples of emoticons, but this is likely what popularized emoticons as we know them today.

PETSCII by Max Capacity, 2014.
ASCII Space by reaktorplayer, 2012. Abstract and eerie.