Year: 2010

On October 2, 2008, after that year's infamous stock market crash, Apple's market cap dropped precipitously to $88.68 billion, while its archrival, Microsoft, was chilling at a comfy $228.35 billion. To the outside world, it wasn't too surprising: Microsoft was the world's largest computer company, and Apple was still the scrappy upstart gunning for the throne. Two years later that all changed. Amid reports that "the Windows era was over," and Apple's consumer gadget dominance, Steve Jobs's company crept past Bill Gates's behemoth. Market value is a tricky figure, but for all intents and purposes, David had finally taken down Goliath.