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The 10 Best Versions of Windows, Ranked



The classic Microsoft Windows logo on a blurred white background

Over the past 35 years, Microsoft has released at least 30 major versions of the Windows operating system. But they weren’t all created equal, so we thought it would be fun to rank the 10 best desktop versions of this essential operating system.

The ranking criteria

When someone says that something was the ̵

6;greatest’, that suggests it had a combination of legacy, impact, innovation and capability for its time. That’s the recipe at play here in this ranking, which is not (and never could be) a definitive list for objectively proving which version of Windows is “the best”.

If you want a list of the ‘best’ versions of Windows, you might get a list of Windows versions with the most features, the fewest bugs, and the most up-to-date security – in other words, a list of Windows versions in chronological order (with a few hiccups). No, this list gets a lot more fun than that.

To keep it simple, we only looked at desktop versions of Windows. Mobile operating systems such as Windows CE, Windows Phone, Windows Mobile 10 and Windows RT are another beast, as are server versions of Windows such as Windows Server 2003.

With that out of the way, let’s rank!

# 10: Windows 3.0 (1990)

Windows 3.0 united the confusingly named Windows 2.x product family (Windows 2.03, Windows / 286, Windows / 386, etc.) into a single environment that ran on machines ranging from low-speed 8088’s to those with 386 CPUs. It also featured a stunning new graphical interface with a 3D shaded look and a series of beautiful icons designed by graphic design legend Susan Kare.

It also introduced Solitaire, which doesn’t hurt.

RELATED: Windows 3.0 is 30 years old: this is what made it special

# 9: Windows 8 (2012)

Change is difficult, and Windows 8 has radically departed from the tradition that has upset many people. Despite poor critical reviews, Windows 8 was the most innovative version of Windows since Windows 95, daring to face the advancing world of touch-based mobile devices such as the iPad head-on. The result was a hybrid operating system that could work on both tablets and desktops.

The result wasn’t the best for desktop users – leaving the Start menu was a mistake – but Microsoft fixed some glaring issues in Windows 8.1. And under the hood, Windows 8 was Windows 7 with many overlooked security enhancements.

# 8: Windows NT 4.0 (1996)

If you take the stability of the 32-bit Windows NT kernel and add the very user-friendly interface of Windows 95, you have Windows NT 4.0. Its rock-solid stability (after a few patches) made it Microsoft’s most popular business and academic operating system for many years, and dedicated NT4 users were reluctant to upgrade until 2003. If it ain’t broke, don’t fix it, right?

In fact, if you were willing to forgo modern interface conveniences and security updates, you could still use Windows NT 4 for some tasks today – if you dared enough.

# 7: Windows 98 SE (1999)

Windows 98 took the innovations introduced in Windows 95 and added an improved interface with more flexibility, while still straddling the 16-bit legacy MS-DOS world. For a time, there was no better operating system for PC games than Windows 98, as it also supported DOS games and DirectX-based titles.

The 1999 “Second Edition” release added a number of improvements (including better USB support) that kept many using 98 until Windows XP was released in 200, skipping Windows Me. Unfortunately, Windows 98 turned out to be hugely unstable, but that didn’t stop it from being a popular upgrade for consumers.

# 6: Windows for Workgroups 3.11 (1993)

Windows for Workgroups did everything right on the popular Windows 3.11 from 1992: support for TrueType fonts, multimedia support, embedding documents with OLE and Minesweeper among them – and added native network support, making it the most powerful consumer and small business version of Windows up to Windows 95.

RELATED: 30 years of ‘Minesweeper’ (Sudoku with explosions)

# 5: Windows 10 (2015)

Windows 10 got off to a shaky start with press criticism of suspicious telemetry calling home to Microsoft, built-in ads, and forced updates interrupting people’s work. But it is to Microsoft’s credit that the company has addressed these concerns over time and has continued to update Windows 10 at a steady pace for the past five years.

Today, Windows 10 is a mature, stable, capable and very popular operating system with more than a billion users. As the “latest version of Windows”, we can expect 10 to continue to grow and change over time as the world changes with it.

RELATED: Windows 10 is great, except for the parts that are awful

# 4: Windows XP (2001)

Even if you didn’t like the green-and-blue motif of XP’s default interface, for many consumers there was something really magical about Windows XP: stability. With XP, many PC users were for the first time upgrading from the unstable MS-DOS roots of Windows 98 and Me.

Along the way, they got a taste of rock-hard Windows NT technology, as the average PC had recently become powerful enough to run it properly. And they did, with many XP fans not wanting to upgrade from XP for a long time.

# 3: Windows 95 (1995)

For many PC users, when “Windows became the Microsoft software product”, Windows 95 was “Windows the indispensable desktop operating system”. It was beautiful and easy to use, and featured the innovative Start menu and taskbar, which surpassed the Macintosh OS in usability for the first time.

Windows 95 introduced many Windows standards that we take for granted today, including File Explorer, Windows keyboard shortcuts, the Recycle Bin, file shortcuts, the modern desktop, and more. It’s the archetype of Windows, distilled: anyone familiar with Windows these days could easily go back and run Windows 95 without a hitch. Few software products were ever so essential in their day.

RELATED: Windows 95 turns 25: when Windows went mainstream

# 2: Windows 2000 (2000)

Windows 2000 is an underrated masterpiece – a taste of a stable and more mature Windows that seemed way ahead of its time to early adopters. As a “professional” version of Windows, it didn’t get the smashing coverage of its consumer counterpart Windows Me. But unlike previous versions of Windows NT, 2000 was a perfectly usable home version of Windows NT for the first time.

It did everything you needed without too much flash, and delivered rock-solid stability that sparked fierce loyalty among users, some of whom didn’t upgrade again until Windows 7 came out in 2009.

RELATED: Reminiscent of Windows 2000, Microsoft’s forgotten masterpiece

# 1: Windows 7 (2009)

At the time of its release, Windows 7 marked Microsoft’s big comeback from the disaster that was Windows Vista, which was pilloried for its new approach to security (UAC), its bugs, its resource-intensive nature, and its flashy. I want to be more like OS X ”Aero interface that didn’t feel like it added much to the OS.

Windows 7, on the other hand, was more stable than Vista, ran faster on the same hardware, reduced UAC issues, and refined the Aero interface to make it less flashy and stylish (and you could turn it off if necessary). At the same time, Windows 7 kept some of Vista’s improvements (such as search in the Start menu) while adding others (such as pinning an icon to the taskbar).

Ironically, much of what still makes Windows 7 great is how it’s not like Windows 10. Windows 7 has no freemium pack-in games, no ads in the Start menu, and no push to cloud your account to link. You update when you think the time is right. It feels like your computer is under your control, not Microsoft’s. In some ways, it’s the last gasp of a non-software-as-a-service era (or as a vehicle for some in-app purchase) that many still desperately cling to, despite the changing technical landscape to us.

With support for Windows 7 finally over from January 2020, you should upgrade to Windows 10 if you can, but it remains to be seen if Microsoft will ever rival the lean, utilitarian nature of Windows 7 again. For now, it is still the best desktop version of Windows ever made.

RELATED: Windows 7 Dies Today: Here’s What You Need to Know




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