Ranking all 12 versions of Windows, from worst to best
I have fond memories of XP and Windows 98 SE, so you can take a guess at mine, but I have colleagues who are much more enamored with Windows 7, or Windows 95. We all have something disparaging to say about Windows 8 though, and the less said about Windows Vista the better.
Ranking the different versions of Windows is about more than what era of computing you grew up in, though. There are some very serious duds in Microsoft’s back catalog, just as there are a few wins too. But whether you can look back on some of Microsoft’s disastrous releases with rose-tinted glasses, or have some genuine love for Microsoft’s missteps, here’s every version of Windows ranked from best to worst.
12. Windows ME
It’s a toss-up as to which is the actual worst Windows operating system, but for us, Windows ME just about takes it, because despite its lofty goals, it failed at almost all of them. It ultimately only lasted a year before it was replaced by the beloved, and infinitely improved, Windows XP.Windows Millennium Edition was the last Windows OS based on MS-DOS, but it restricted access to DOS to improve boot times. This made it the worst of both worlds, as it couldn’t benefit from the improvements found in the Windows NT kernel, which formed the base of Windows XP, but also didn’t provide proper DOS functionality either.
Windows ME was plagued by poor driver support and incredibly bad stability issues. It is known for how frequent it would crash, and not just once you had it up and running. There are myriad reports of its crashing during installation and setup, and much-touted features like System Restore often didn’t work properly in protecting affected systems.
It tried to do a few innovative things, like introducing automatic security updates, folder compression with native ZIP support, and a new Help and Support system to make it easier to fix things. But none of that makes much of a difference if the core OS is barely functional.
Windows ME was a mess, and from our perspective, is the worst version of Windows ever released.
11. Windows 8
Windows 8 feels like Microsoft hit the panic button in its developer offices. Tablets and smartphones were taking over the world and the PC was dying, so Windows needed to be more compatible with tablets. It tried to make the Windows desktop a better fit for the emerging tablet scene, and it succeeded to some extent, with its tile design and gesture controls making it enjoyable to use on a tablet. Unfortunately, it was completely unintuitive for experienced and novice desktop PC users, turning off longtime Windows fans immediately.