Crazy Eddie is Coming for Windows 11 (Premium)

In 1986, Steve Ballmer starred in a widely misunderstood internal video parody advertisement for Windows 1.0. But today, it seems prescient. What would it take to get you to upgrade to Windows 11? Or from Windows 11 Home to Windows 11 Pro?

How does $10 sound?

Let me quickly address the Steve Ballmer video first. If you Google this, you'll find references to this video being a "1986 Windows Ad," "Steve Ballmer promoting Windows 1.0 in 1986," and so on. These are all incorrect. We forget this, but Microsoft used to record funny and corny videos internally to share with the company, and they were so popular that they would show them during Bill Gates keynotes at events. (One famous and memorable example: Bill Gates and Steve Ballmer spoofing the then-current VW "Da-da-da" ads.)

The Steve Ballmer video for Windows 1.0 is just a parody, an internal production that accomplishes exactly what it and so many future videos set out to do: Educate while being funny by spoofing something that was then well-known. In this case, it was spoofing the "Crazy Eddie" TV ads of that era. For example, this one. As for educational, once you're done laughing at Ballmer's over the top presentation, you'll discover that Windows 1.0, a little-understood, poorly selling product, arrived with significant advantages over plain MS-DOS. And you got all that ... wait for it ... for the low, low price of $99.

Windows has changed a lot over the years, and anyone who's been there for the duration will remember the highs and lows. The sudden surge in popularity with Windows 3.0 and 3.1. The explosive excitement of Windows 95. The partial switch to the NT codebase--and the loss of the NT brand--with Windows 2000. The blue and green experiences of Windows XP ... and the resulting security nightmare that spawned Trustworthy Computing. The year's long wait for Longhorn ... and the resulting disappointment in Windows Vista. You know the drill.

Today, Microsoft is careening toward the end of support for Windows 10, the most popular version of the product Microsoft has ever made by usage. But as Laurent pointed out yesterday, Windows 10 still commands about 63 percent usage share just months ahead of that support expiration. This is unprecedented. Windows 7, the second-most popular Windows version by usage, had about 25 percent usage share by this point in the life cycle, and its replacement, Windows 10, already dominated, with 68 percent usage share.

There is so much to unpack here. And it is far too easy to look at this situation and invent a single cause. But I think the truth is far more nuanced, that there are many things that contributed to the situation in which Microsoft now finds itself. What I can say is that this isn't because Windows 11 is somehow lacking in some way. Yes, that was true when the system first appeared in 2021. Indeed, its functional regressions are the stuff of legend. But not today.

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