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.

Trollface is a rage comic character wearing a mischievous smile that is meant to represent the facial expression of an Internet troller. Commonly used to portray a character as a troll in rage comics, or alternatively, to identify oneself or another participant as such in online discussions.