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Windows Me

Windows Me
Windows Me Screenshot: LGR/YouTube (Other)

Not even a cute name could save Windows Me from being dubbed the worst Windows ever. Released in 2000 as the third update to Windows 98, Windows Millennium Edition (or Windows Me), was meant as a stopgap between Windows 98 and XP, which was in development at the time Me arrived and would be released to the public a year later.

Initially, reviews for Windows Me were mixed, with several sites praising the OS for its improved hardware and software compatibility over even Windows 2000 (which had also been released as a business-oriented OS seven months earlier). Others, like PCWorld’s Dan Tynan (who dubbed it the “Mistake Edition”) criticized its poor reliability. After all, Windows Me was clinging on to an aging 9x platform and Windows 2000 wasn’t ready for consumers.

In the end, Windows Me was only ever a bridge between the old and the new Windows, and not enough people felt compelled to spend money on an OS that would only stick around for a year. Although it was a failure, Windows Me improved boot speeds and introduced several innovative features still used today, including system file protection, auto-update, hibernate, Movie Maker, photo sharing, system restore, and more.