A company that's been around as long as Microsoft will inevitably have a history of presentations that have gone so far off the rails they've ended up somewhere in the next county. You've got Steve Ballmer shouting "DEVELOPERS!!!" while sweating through his shirt, Don Mattrick sinking the Xbox One before it had even set sail, and on and on. But I hold a special place in my heart for the time Bill Gates went on stage at the height of his power to show off Windows 98, fresh from the world-changing but notoriously buggy Windows 95—and watched it crash mid-demo.
The moment, captured above, was from Gates' keynote at the then-major COMDEX trade show a few months before Windows 98's launch. Microsoft's Chris Capossela was in the middle of demonstrating a novel feature—plug-and-play USB support—by hooking up a scanner, prompting Windows 98 to download its drivers. Then, wham: Blue Screen of Death.