On 22 October, across four millennia, humanity has watched the sky with varying degrees of success and consequence. In 2137 BC, two Chinese court astronomers reportedly paid with their lives for failing to predict a solar eclipse under Emperor Zhong Kang, an event that may represent one of the earliest dated astronomical records in history. In 1739, British forces attacked the Venezuelan port of La Guaira in the opening salvo of the improbably named War of Jenkins’ Ear, a conflict sparked by colonial trade tensions and a preserved body part presented to Parliament. In 1797, André-Jacques Garnerin became the first person to make a recorded parachute jump, descending violently but successfully from 1,000 metres above Paris in a frameless silk canopy. And in 2024, asteroid 2024 UQ became only the tenth space rock detected before atmospheric entry, burning up harmlessly over the Pacific. From ancient celestial divination to modern near-Earth object tracking, 22 October offers a peculiar thread through human attempts to understand, survive, and occasionally fall through the sky above us.