Trollface was drawn in Microsoft Paint on September 19, 2008, by Carlos Ramirez, an 18-year-old Oakland college student. The image was published on Ramirez's DeviantArt page, "Whynne", as part of a rage comic titled Trolls, about the pointless nature of trolling. Ramirez posted the image to the imageboard website 4chan, where other users began to share it. 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.

Carlos Ramirez is the original created of The Trollface. He is an artist that is known by his deviantART. He revealed that The Trollface was based off a drawing of a comic character he drew, “Rape Rodent” (seen below).