Trollface

A leering, wide-mouthed face drawn in Microsoft Paint, used to mark the moment a joke was at somebody else's expense. It was one panel of a rage comic called Trolls, drawn on 19 September 2008 by Carlos Ramirez, an eighteen-year-old college student in Oakland, and published to his deviantART page under the name Whynne.

It first appeared in 2008, during early YouTube.

Trollface is the oldest and most widely recognised of the rage faces, and the one that escaped the format. Ramirez's comic was mocking trolls; the face was immediately adopted by them, and became the universal shorthand for deliberate provocation online. Ars Technica's 2012 field guide to rage faces treats it as the anchor of the whole vocabulary, and it has since appeared on Turkish football terraces, in a Black Mirror episode, and on hijacked Russian military radio frequencies.

Ramirez registered Trolls with the US Copyright Office in 2010 and told Kotaku in 2015 that licensing it had earned him over $100,000, with peak months around $15,000 — an early demonstration that a meme could have an owner, and that the owner could enforce it. A Wii U game was pulled for using the face without permission.