Unfortunately deviant art does not give us the exact date that an image was posted:
http://whynne.deviantart.com/art/Comic-Trolls-98357844?offse...
Cool face seemed to be posted first in 2008-12-01 and trollface somewhere in 2008.
http://whynne.deviantart.com/art/Comic-Trolls-98357844?offse...
Cool face seemed to be posted first in 2008-12-01 and trollface somewhere in 2008.
But that doesn't matter that much since it was originally posted on 4chan and not DA.