Trollface

Trollface stands as one of the most iconic and influential memes in internet history, evolving from a simple MS Paint comic about trolling culture into a universal symbol of mischievous online behavior that generated significant commercial success and legal controversies while shaping the entire rage comic phenomenon.

The meme originated on September 19, 2008, when Carlos Ramirez, an 18-year-old Oakland college student known by his DeviantArt handle "Whynne," uploaded a MS Paint webcomic titled "Trolls" to his DeviantArt page. The comic was created to illustrate "the pointless nature of trolling on 4chan's /v/ (video games) board" (Know Your Meme, 2009). In the DeviantArt post, Ramirez revealed that he was attempting to draw a comic character known as the "Rape Rodent," but the final result became something entirely different and far more significant.

The distinctive face featured in the comic—characterized by a mischievous grin and raised eyebrows—was designed to represent "the facial expression of an Internet troll." Ramirez's creation was intended to highlight how some individuals use the pretense of trolling to excuse themselves from poor reasoning in online debates, essentially making trolling "the ultimate cop-out and the new Godwin's law for Internet debate" (DeviantArt, 2011).

Initially, the face became known as "Coolface" after a rage comic-style webcomic featuring the image took off on 4chan and eBaum's World, though this alternate name was short-lived (Know Your Meme, 2009). The image gained significant traction throughout the first half of 2009, particularly among Redditors and rage comic artists, coinciding with the rapid growth of the /r/f7u12 subreddit dedicated to rage comics.

Search queries for Trollface began appearing in January 2009, several months after the original DeviantArt posting, indicating the meme's gradual but steady rise to prominence. On August 1, 2009, the first Urban Dictionary definition for "Trollface" was submitted, marking its entry into mainstream internet vocabulary.

The meme's versatility and recognizability led to thousands of webcomic and photoshopped instances appearing across platforms including Tumblr, Cheezburger, Reddit, Facebook, Quickmeme, and Memegenerator. The image became the universal emoticon for internet trolling and served as a versatile rage comic character, often accompanied by the catchphrase "Problem?" in various contexts.

Ramirez's business acumen proved as significant as his artistic creation. He registered the copyright for Trollface with the United States Copyright Office on July 27, 2010, and subsequently earned substantial income from licensing fees and legal settlements. In a 2015 Kotaku interview, Ramirez estimated that he had earned more than $100,000 from the image, with monthly revenues reaching as high as $15,000 at peak popularity (Wikipedia, 2025). His licensing deals included partnerships with retail chain Hot Topic for t-shirts featuring the face.

The commercial success led to several legal disputes. On July 16, 2011, Ramirez sent emails to Reddit claiming that the use of Trollface violated his copyright and requesting removal of related content (Know Your Meme, 2009). The Reddit community responded by changing the background image for f7u12 pages to feature Trollface with the text "HEY WHYNNE… U MAD BRO?" demonstrating the complex relationship between meme creators and the communities that popularize their work.

A notable copyright enforcement case occurred in March 2015 when Ramirez issued a DMCA takedown notice to Nintendo, resulting in the removal of "Meme Run," a Wii U video game that featured Trollface as the main character. Ramirez explained that his licensing agreements with other parties compelled him to address copyright infringement, stating that resolution typically involved proper attribution, monetary compensation, or removal (Rage Comics Wiki, 2025).

In 2020, Trollface experienced a significant resurgence through ironic memes, particularly the "Cover Yourself in Oil" format, which originated from a Troll Science comic and became popular for its absurdist logic. This revival led to new variations like "Trollge," a more sinister version of the character that became associated with creepypasta-style content.

The meme's cultural significance extends beyond internet humor. La Tercera described Trollface as "the father of memes," and it was featured in a bust exhibition at Mexico City's Museo del Meme, demonstrating its recognition as a significant cultural artifact (Wikipedia, 2025).