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The Worst Version of Windows Is…

Rob Pegoraro
Contributing Editor
Yahoo Tech

Microsoft has something new for us today: Windows 10, the next major release of its desktop operating system. It gets a public unveiling in Seattle this morning.

Watch: We live-blog the Windows 10 announcement.

Window 10 should be a welcome development to those of you who regard Windows 8 it as the worst version of Windows ever made. There are certainly a lot of you. But what if Windows 8 does not actually represent the worst of Microsoft’s desktop operating systems?

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If you’re sufficiently cranky, you can make a case for any consumer version of Windows over the last 20 years being the worst ever. And we are. So we did. Here’s the logic:

Windows 3.1: Crashed if you looked at it sideways. Remained incapable throughout its long life of getting on the Internet without third-party software (anybody remember the joys of configuring Trumpet Winsock?). So inept at gaming that most action titles required booting to DOS. Often demanded editing of config.sys and autoexec.bat files; wouldn’t let you give files names longer than eight characters. 

Windows 95: Graced us with install and uninstall “wizards” that were more diabolical than wizardly. Got the term “DLL hell” into even wider circulation. Some of its icons and dialogs still surface in Windows 8 (take the clumsy network-adapter-properties window… please). Launched amid a torrent of hype that should shame all involved, not least those of us in the media. 

Windows 98: Its long list of bug fixes and performance tweaks served as a reminder of how much was left unpolished or outright unfinished in Win 95 and could only be fixed by shelling out $109 for this update. “Active Desktop” and “Channels” features brought Web content out of the browser but also set Microsoft down the path that left Internet Explorer 6 catastrophically insecure. As our friend Larry Magid told CNN at the time: “It should have been Windows 97 or Windows 95.5.”

Windows Millennium Edition: “Windows Me” ranks second only to “Microsoft Bob” in many people’s lists of worst operating-system titles ever. Removed support for some DOS tools without making the system as a whole that much more stable. Came with a version of Windows Media Player that copied your CDs as Windows Media Audio files instead of MP3s andthen treated you like a thief by tying down those WMAs with “digital rights management” restrictions. 

Windows XP: Shipped in a horribly insecure configuration—yet the same developers who left numerous ports and services open to exploitation somehow thought it necessary to make you type every WiFi password twice. No decent backup or anti-virus tools built-in. Abused as a bloatware carrier by PC manufacturers. Depressingly successful: Zombie-like persistence (abetted by developers who can’t be bothered to update their software to run on any newer versions) apparently means we will never, ever be free of it.

Windows Vista: Windows desperately needed a security update at this point. But Vista’s incessant “User Account Control” dialogs—which could surface when you least expected it—were not the way to go about it. Sleek “Aero Glass” shown in Microsoft’s ads wouldn’t run on PCs that had been sold as “Vista Capable.” If Vista’s ongoing “validation” checks determined you weren’t running a licensed copy, the system treated you like a thief and could even lock you out of Windows. Ravenous appetite for memory and processor cycles.

Windows 7: Punished users who sat out Vista by requiring a destructive upgrade from XP—you had to back up and reinstall files and settings, then reload every single app. Outdid Vista’s ridiculous five-edition product matrix by shipping in six different flavors: Starter, Home Basic, Home Premium, Professional, Enterprise and Ultimate. (Rumors of an additional “Mauve” edition that tested poorly in focus groups are untrue.) Replaced the core set of folders for documents, pictures, music, movies, etc. with “libraries,” a move so popular that Windows 8.1 hides libraries by default.

Windows 8: The Metro Modern TileWorld half of this two-faced release, with its absence of menus and even windows, was optimized for touchscreens when the vast majority of Windows PCs still relied on mice and touchpads. Meanwhile, Win 8’s desktop half was a challenge to operate by touch unless you had fingertips the diameter of chopsticks. Should have rewritten the overgrown mess that the Start menu had become, but instead ripped it out completely.

(We’re leaving out Windows NT and 2000 because so few home users had to deal with those office-focused releases. But we could complain about them too. Don’t get us started.)

Windows 10: We’re sure it’s going to be perfect.

Read more: See all Yahoo Tech’s Windows coverage

Email Rob at rob@robpegoraro.com; follow him on Twitter at @robpegoraro.