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Trollface is a black and white drawing of a face with a large mischievous grin that is meant to portray the expression someone makes while trolling. Posting a Trollface image into a forum thread is often used to claim that someone was being fooled or intentionally angered. The face commonly appears in rage comics indicating that the character is being mischievous in some way.
A MSPaint comic made by deviantArt user Whynne about the pointless nature of trolling on 4Chan’s /v/, was uploaded on September 19th, 2008.
In his deviantART post, Whynne claims he was attempting to draw a comic character known as “Rape Rodent”:
Trollface has also been called “coolface”, which came from a comic posted to 4chan after the original trollface:
Search queries did not pick up until January of 2009, several months after the original deviantArt posting.
Whynne Claims Copyright Infringement
On July 16th, 2011, a screenshot of an email from a man named Carlos Ramirez claiming to be Whynne was posted to Reddit. The email stated that the use of Trollface on Reddit violated his copyright on the image, and that he would like to have the subreddit removed.
You know what also makes me happy? Trolling reddit and seeing a shitstorm like this develop.
The background image for the f7u12 pages was changed to a picture of trollface with the text “HEY WHYNNE… U MAD BRO?”: