Trollface was drawn in Microsoft Paint on September 19, 2008, by Carlos Ramirez, an 18-year-old Oakland college student. [ 3][ 4] The image was published on Ramirez's DeviantArt page, "Whynne", [ 4] as part of a rage comic titled Trolls, about the pointless nature of trolling. [ 5][ 6] Ramirez posted the image to the imageboard website 4chan, where other users began to share it. [ 3][ 7] In the following months, Ramirez's drawing quickly gained traction on 4chan as the universal emoticon of an internet troll and a versatile rage comic character.

The Trollface was originally drawn by Carlos Ramirez, an Oakland-based artist known by his DeviantART handle Whynne, as part of a MS Paint webcomic about the pointless nature of trolling on 4chan 's /v/ (video games) board.

Kotaku reports that the black-and-white cartoon face was originally drawn by 24-year-old Carlos Ramirez, and since 2008, he’s made more than $100,000 off of his creation. Ramirez drew the cartoon 7 years ago and posted it to anonymous imageboard 4chan, and it immediately exploded in popularity.