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Various American Commodore 64/128 BBS-software from the 80s and 90s. via
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.
ASCII video conversion by Andy Wallace, 2011, with an interesting choice of font.
Knitoscope Testimonies by Cat Mazza, 2006. An animation in cross stitch of interviews with various individuals working within the labor movement. via.