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EVERY MICROSOFT WINDOWS OPERATING SYSTEM, RANKED

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May 2025

HONORABLE MENTION GOES TO WINDOWS NT, WHICH FORMS THE STABLE FOUNDATION OF MANY OF WINDOWS' BEST OFFERINGS.

- BY MARK HACHMAN

EVERY MICROSOFT WINDOWS OPERATING SYSTEM, RANKED

What was Microsoft's best Windows operating system of all time? If you're like us, you have...opinions. Even if you're not the type to parse through all of the little details that separated Windows 98 from Windows 95, say, you certainly had a favorite Windows OS that you grew up with and cherished-and then you fumed when Microsoft replaced it with something different.

Likewise, you had versions of Windows you probably detested. Maybe you even (gulp) tried Linux? (Nah.)

But ranking each version of Windows? As in picking a winner? That's where the fun lies. I've ranked every major consumer version of Windows, from worst to best. As Microsoft celebrates its 50th anniversary, see if you agree with what I've picked.

imageWINDOWS 2.0 (1987)

Although I grew up with Windows, I have no memory of Windows 2.0, and I'm not sure you do, either. (A YouTube video provides a tour of Windows 2.0 [fave.co/4jnmRSR], if you're interested.)

History tells us that Windows 2.0 subsumed Windows 1.0's tiled applications and allowed them to overlap one another, which would be a relatively big deal for the tiny, low-resolution monitors of the 1980s. Add to that early versions of Word and Excel, and Windows PCs were in their infancy as productivity PCs. Another key upgrade was the Control Panel, which provided Windows settings before Windows Settings was Settings, if you know what I mean.

Windows 2.0 set up Windows 3.0 by allowing a protected mode kernel that allowed multitasking of MS-DOS applications, but Windows applications all shared a virtual MS-DOS machine. Microsoft engineers were also ensnared in the OS/2 project with IBM, which may have also lessened Windows 2.0's impact.

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This story is from the May 2025 edition of PCWorld.

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