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On 19 September 2008, an 18-year-old student in Oakland uploaded a deliberately crude drawing that became one of the internet’s most recognisable images. Trollface, created by Carlos Ramírez in Microsoft Paint, evolved from a joke comic about online provocation into a copyrighted icon that earned its creator hundreds of thousands of dollars. But the 19th of September holds darker stories too. In 1991, hikers in the Ötztal Alps discovered a 5,300-year-old murder victim, the oldest known homicide case in history. The body, now known as Ötzi the Iceman, revealed extraordinary details about Copper Age life and a violent death from an arrow wound. Mexico’s relationship with this date is particularly haunting. After the devastating 1985 earthquake, the country instituted annual drills on 19 September. In 2017 and again in 2022, real earthquakes struck during those commemorative drills, an eerie statistical coincidence that reshaped how Mexicans understand disaster preparedness. Finally, in 1980, a dropped socket wrench at a Titan missile silo in Arkansas led to a fuel leak, an explosion, and a nuclear warhead thrown into a ditch, a near-catastrophe triggered by an eight-pound tool. Four very different stories, one date, and proof that history keeps excellent notes on human overconfidence.