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, cherished, and then fumed when Microsoft replaced it with something different.
Likewise, you had versions of Windows that 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.
Windows 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, if you’re interested.)
History tells us that Windows 2.0 took Windows 1.0’s tiled applications and allows 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: the Control Panel, which provided Windows settings before Windows Settings was Settings, if you know what I mean.
Windows 2.0 and some applications.
Microsoft
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.
Windows ME (2000)
Windows Millenium Edition (Windows ME) paralleled Windows 2000 as a consumer-first operating system still tied to the legacy of MS-DOS, but didn’t exactly overwhelm users with its new consumer features like Windows Movie Maker and updated versions of Windows Media Player and the Windows DVD Player. Windows ME wasn’t really stable and didn’t perform especially well, either, which made the included System Restore a more necessary feature than you might otherwise think. (ME also automatically downloaded and installed updates.)
Windows ME left support in June 2002, a quick exit after launching in Sept. 2000. Windows XP launched on Oct. 25, 2001 on the stable Windows NT kernel, which meant that ME’s lifespan was about one year. in 2006, PCWorld characterized Windows ME as “Windows Mistake Edition” and included it in the 25 worst tech products of all time.
Windows 1.0 (1985)
Iconic! Windows 1.0 marked the transition from the text-based world of MS-DOS into the visual world of the GUI, which had taken off with 1983’s release of the Apple Lisa. Naturally, Windows 1.0 necessitated a mouse, bringing that pointing device even more into the mainstream. While MS-DOS was just a single-tasked OS, Windows also used preemptive or cooperative multitasking for programs to release their resources so that other programs to use them.
Windows 1.0 featured tiled windows.
Microsoft
Windows 1.0 was the necessary first step, the one which launched generations of iteratively improving visual computing and identified Microsoft-centric PCs as “Windows” PCs. But it was still rudimentary — the “windows” were just tiled, for example. Overlapping windows debuted in Windows 2.0.
Windows 8 (2012-2013)
We could have separated Windows 8 and Windows 8.1 into separate items, too, but that would have forced me to write about Windows 8, twice. That’s intolerable, so I’m jamming all my distaste for Windows 8/8.1 into a single entry.
What we all hated about Windows 8/8.1 was the godawful “Modern” tablet interface that Microsoft forced upon us, and the awkward tablet-esque app experience that accompanied it. Windows 8 also included Charms, the quasi-taskbar that appeared when moving to the right-hand side of the interface. (Live Tiles worked wonderfully, eventually, on Windows Phones, and I loved the implementation into Windows 10’s Start menu, too.)
manaemedia/Shutterstock.com
Windows 8.1 allowed you to boot directly to the desktop, though it wasn’t really the true desktop that we’re all used to — even though the Start button was there, it still brought you back to the Modern tiles unless you configured it to show you a list of apps. Start did allow you to shut down your PC directly from the Start button, however.
All I recall about Windows 8 and Windows 8.1 was trying to keep it together until the first previews of Windows 10 debuted in 2015. Thank goodness Windows 8.1 finally ended support in 2023 and was banished forever. But why didn’t Windows 8 give way to Windows 9?
Windows 2000 (2000)
Windows 2000 was essentially an experiment: give business or power users their own operating system, and let consumers (with Windows ME) have their own, as well. It ran on the Windows NT kernel — which, if it wasn’t originally designed for workstations and servers, we’d probably call out as an honorary mention.
As Wikipedia notes, Windows 2000 was designed to be stable and secure. On that last point, however, it wasn’t; portions of the source code leaked to the Internet, and Windows 2000 was attacked via Code Red and Nimda.
Windows 2000 basically took Windows 98 features such as Internet Explorer and brought them on to the Windows NT kernel, along with FAT32 support, Windows Media Player, Internet Connection Sharing, and more. Windows File Protection was a new feature, along with USB 2.0 device support and the ability to drop into hibernation.
Windows 3.0 (1990)
Windows 3.0 began life as a skunkworks project to run Windows applications in separate protected memory segments while maintaining backwards compatibility with MS-DOS, using what former Windows president Steven Sinofsky called “hacks” to Intel’s hardware like the “PrestoChangeoSelector.” It was so impressive that Microsoft backed it with a $3 million launch.
Windows 3.0’s desktop.
Microsoft
Windows 3.0 looked significantly cooler, adding to its appeal, with support up to 256 colors. Under-the-hood improvements such as the ability to share data between applications complemented the introduction of the File Manager and Program Manager, as well as the ability to run in different “modes” to support older Intel 286 processors as well as the more modern 386 via an “enhanced” mode.
As you may recall, Windows 3.0 didn’t attract games, as the vast majority of games at the time ran under DOS. That’s a bit ironic, given that Windows 3.0 with Multimedia Extensions (1991) added a Media Control Interface for sound and graphics cards, as well as the Media Player program. But the real irony is that Windows 3.0 launched Windows Solitaire, which is still the grand daddy of all time-wasters.
Windows 3.1 (1992)
The question that we asked while putting together this list: should Windows 3.1 be considered separate and distinct from Windows 3.0? For the purposes of this list, yes — there’s enough to draw distinctions between the two. (We’ll disagree about Windows 8 and Windows 8.1, though.)
Much of our list focuses on standalone iterations of the Windows operating system. A key exception is Windows 3.1, which really transformed Windows and Windows PCs into multimedia machines. As a enthusiast, Windows 3.1 is the version of Windows 3.0/3.1 that I consider to be the more important. It’s still a Microsoft milestone.
Windows 3.1 allowed for windows to be superimposed over one anothe.
IDG
Windows 3.1 introduced the era of screensavers, MIDI files (played back via Media Player), SVGA graphics, Sound Recorder, and a distribution method on CD-ROM. This release even saw Microsoft ship Video for Windows. Underneath the hood, Windows 3.1 also introduced the Windows registry, with drag-and-drop file management and even quick formatting. TrueType scalable fonts were included, as well.
It’s easy to focus on Windows 3.0 and Windows 3.1 as two versions of the same OS, but they weren’t; Microsoft even charged more. Microsoft sold Windows 3.0 for $149, but offered Windows 3.0 for $50 for those who owned a previous license, Wikipedia noted. Microsoft charged the same $149 for a retail copy of Windows 3.1.
Windows 98 (1998)
It’s not fair to call Windows 98 a service pack for Windows 95, but this 1998 consumer operating system was very influenced by Windows 95. Its chief features were support for the emerging standard of DVD-ROMs, as well as its support for early USB hardware. But Windows 98 essentially served as a gateway to the Internet for Windows, with the Active Desktop allowing active Web content to be added to the desktop and Internet Explorer 4.0 debuting.
Wikipedia
Windows 98 was also the first time we saw Windows Update be added to Windows, allowing patches to be pushed to client PCs, and Windows Cleanup, which set the stage for Storage Sense to de-clutter the user’s hard drive and enable more usable space.
Windows 98 was a minor release of Windows. But as a follow-on to Windows 95, it ranks decently as a result.
Windows Vista (2007)
Windows Vista wasn’t the worst of Microsoft’s operating systems, aesthetically. Vista (the first Windows OS to ship on a DVD-ROM) featured the glassy look of Windows Aero, and shipped with a perfectly serviceable Start menu, taskbar, and the new Windows Sidebar that basically served as a repository for Windows widgets.
Microsoft was determined to make Vista secure, however, and the infamous User Access Controls (UAC) proved to be its undoing. UACs annoyingly popped up frequently, asking users whether they in fact wanted to take an action that Windows might deem unsafe. (Users, just wanting to get on with it, would just keep approving them.) BitLocker drive encryption also debuted on the premium editions, while Backup and Restore helped protect user data. Microsoft debuted ReadyBoost to basically turn flash drives and available system RAM into cache, but users complained that Vista ran slow anyway.
Microsoft
Vista demanded good hardware, was a pain to use, and required several service packs, one of which allowed users to change the desktop search program because of antitrust concerns raised by Google. Microsoft has a reputation for shipping alternating bad than good operating systems, and Vista’s position between Windows XP and Windows 7 just perpetuated that.
Windows 7 (2009)
Like Windows 10, Windows 7 was primarily an apology of sorts for its predecessor, Windows Vista. Based upon Windows NT, the Windows 7 operating system significantly boosted performance in terms of boot and shutdown times, while minimizing the constant interruptions that Vista’s UACs introduced.
Foundry
Windows 7 maintained and expanded upon the visual themes that Windows Vista introduced. Right-clicking launched “jump lists,” which remain today. The Taskbar (with the ability to pin apps) was a significant upgrade, and File Explorer added “libraries” which stored the user’s documents, videos, music and more. BitLocker, Windows Defender, and Security Essentials added additional security. The OS also was the first to recognize the power of SSDs, with a specific TRIM command to optimize them, as well as virtual hard disks.
Windows 7 was where Microsoft started to get a little crazy in terms of various editions of the operating system, including Starter, Home Basic, Home Premium, Professional, Ultimate, and Enterprise, all differentiated by different feature sets. You also got to choose: did you want a 32-bit copy or a version for the latest IA-64 processors? (Read our Windows 7 review.)
Windows XP (2001)
Microsoft’s best versions of Windows don’t try to do too much, serving as a unified foundation for business productivity users and consumers alike. Windows XP did just that — basically taking Windows 2000’s reliance on the stable Windows NT kernel and adding consumer features, or, alternatively, taking Windows Me and applying a bit of sanity to it.
IDG
To some, Windows XP’s Start menu — a straightforward list of apps and functions — still remains the best ever. Ditto for the background wallpaper, Bliss. XP didn’t add that much: ClearType rendered fonts better on LCD displays, prefetching sped up boot times and helped enable fast user switching. Remote Assistance and Remote Desktop began making life easier for relatives asked to do tech support.
For the time, there was a big black mark: Windows Product Activation, which meant that Windows would essentially not function without the proper code. That led to a new generation of headaches for people buying or building or upgrading PCs. But XP still remained immensely popular even years later, because it just worked.
And it was! The Start menu and Taskbar still aren’t great, while the Widget menu is basically a collection of the digital crap you find at the bottom of tech media web pages. And who can forget the fiasco of Windows 11’s hardware requirements? But four years on, I love what Microsoft Snap and the Settings menus are evolving into. Microsoft dumped Teams Chat, and the hardware issues have gone away.
Windows 11’s Start menu was a step back.
Foundry
Today, Windows 11 is almost a separate OS, predicated (somewhat, but not entirely) on AI. But there’s still a lack of cohesion. Copilot was an integral part of the operating system, with the ability to actually change Settings; now it’s not, and Copilot is an app that can be ignored or reviewed (or in the case of the Copilot keyboard key) repurposed. AI features within Paint and Photos range from the weird Cocreator to the underappreciated, practical AI tools in Photos. Recall was an enormous scandal and now is largely forgotten.
I hate to say it, but Windows 11’s AI focus basically is asking for Windows 12: an operating system designed for AI from the ground up. (Put down your pitchforks, please!) Sure, Windows is always evolving, but Windows 11 still feels like Microsoft is making it up on the fly.
Windows 95 (1995)
With Windows 95, Windows went mainstream. Suddenly, Windows was crossing the threshold from an OS that people had to use — or that nerds enjoyed tinkering with — into something that mainstream America almost thought was cool. Of course, some of that was due to the marketing; the Rolling Stones’ “Start Me Up” proved to be a perfect fit, though the “You make a grown man cry” lyric never made it in. Even the startup sound came from the keyboard of Brian Eno.
Foundry
Though you could access MS-DOS, Windows 95 marked a clean break from the MS-DOS era, running in 32-bit mode. (Today, you can run Windows 95 in your browser.)
Of course, Windows 95’s iconic feature was the Start menu, followed by the introduction of the Taskbar and what was then known as the Notification area. While it didn’t include Microsoft’s Internet Explorer, later versions did. Windows 95 also introduced the concept of “plug and play.” Just install the new hardware, and it works!
Windows 10 (2015)
For all of you who think that Windows 95 should sit atop our list for its profound cultural impact — absolutely not. Windows 10 still commands over 58 percent of the worldwide market, even though it’s staring down the end of support in October 2025. Consumers still love it, and Windows 10 still offers the most modern, attractive, and cohesive interface in existence.
Windows 10: it just makes you want to sit down and Start.
Mark Hachman / Foundry
Yes, Windows 10 introduced the redesigned Start menu, with the bright, bold, adjustable Live Tiles that could be pushed around like a magic square puzzle to create the arrangement you wanted.
But for me, it’s the little things you’ve forgotten about. Sure, Windows 10 requires a license, but it was a free upgrade, and yours for life. In 2019, the free Windows Security/Windows Defender became so good that you could stop paying for antivirus software. And hello, Windows Hello? Biometric identification basically spelled the end of the password, and who doesn’t want that? Even Microsoft Edge became good enough that you didn’t need to rush out and replace it with Google Chrome.
Windows 10 became the foundation of an ecosystem of Windows devices that all ran on a common platform. Sure, Windows Phones — a cult classic to this day — died due to lack of apps. Windows Mixed Reality never even started taking off.
On the PC, though, Windows 10 was welcoming, personable, and very much yours. Windows was Cortana’s Jen Taylor, cheerily offering to help. Windows Spotlight, the Xbox app, the Start menu: the world was bright, the world was hopeful, and your modern PC wanted you to use it. Windows was never better than this.
by #AI [2.0] April 4, 2025 · Automatic / Editor's Picks [News]
