Windows 8: Still Crazy After All These Years (Premium)

Some seem surprised that it took so long for Windows 10 usage to surpass that of Windows 7. But this belated milestone doesn’t say that much about Windows 10, or about Windows 7. Instead, it says a lot about Windows 8.

Which was, of course, terrible.

The ways in which Windows has evolved over the years are many, but it’s rarely happened on a steady schedule. The one exception is the trio of releases that included Windows 7, Windows 8, and Windows 10, each of which shipped three years after its predecessor. That release cadence was so regular that many probably forget that Microsoft had never previously used such a schedule. Or kept to any schedule at all, really.

Instead, that steady three-year release cycle was a reaction to the Longhorn delays and the subsequent poor reception to Windows Vista. Longhorn was supposed to be a major release, the biggest ever, and it was envisioned as a complete rethinking of the platform. But it was also too much to take on at once, and the project collapsed under its own weight, taking Jim Allchin and his career with it. Windows Vista, which was hastily cobbled together in the wake of Longhorn’s demise, provided only shallow hints at the Longhorn promise, with features like virtual folders, hardware-accelerated graphics, and a widget-filled Sidebar.

Windows Vista shipped in just a year and it did so with major compatibility and performance problems, forever ensuring that it would be remembered as one of the most disappointing Windows versions of all time. But fixing Vista was simple, and I’ve often described Windows 7 as being nothing more than another Vista service pack. But despite its easily-attained goals, Windows 7 has gone on to be, perhaps, the most well-respected version of Windows, ever.

And the reason for that, of course, is Windows 8. Which, again, was terrible.

Actually, “terrible” isn’t the right word because it doesn’t do anything to explain how thoroughly and perhaps permanently that release undermined Windows as a platform and set up a coming decade of client defeats for Microsoft. Compared to Windows 8, Vista was just a minor setback, one that was easily and quickly fixed. But Windows 8? We’ll never stop dealing with the blowback from this perfect combination of terrible feature set and bad timing.

Windows 8 only happened because of Windows 7’s perceived successes. Microsoft’s leadership team gave an insane madman, Steven Sinofsky, free reign to make any changes he wanted to drag Windows quickly into the then-nascent era of mobile, touch-based computing. Sinofsky was no visionary, but he was dictatorial. So he was basically everything that was wrong about Steve Jobs, but lacking in what made Steve Jobs special.

The result was a disaster, a product that borrowed heavily from Microsoft’s Windows Phone platform without ever stopping to wonder whether being able to do so made any sense at all for the PC market. Worse, after stealing ideas from Wi...