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

While the comic was first uploaded in 2008, it has made a huge resurgence in popularity starting in 2020 with memes such as "Cover Yourself in Oil."