No. I don’t like XP.

For me it would be Windows 2000.

When it was released its competition was

- Mac OS 9 (which was about as reliable as Windows 98)

- OSX wasn’t yet released. But when it did, it wasn’t particularly great for existing Mac users. It took a few years for OSX to really gain momentum.

- Linux (who’s desktop support was still immature)

- BeOS 5 (which was bloody awesome, but also very niche)

- Windows Me (easily the worst desktop OS Microsoft have ever produced. Say what you will about Vista, but its flaws were a combination of its ambition and Microsoft “certifying” it for hardware that wasn’t powerful enough. Whereas Me just sucked in every conceivable and irredeemable way).

Windows 2000 was the first time Microsoft but focus on the little details. For example Notepad was finally given hot keys like ctrl+s to save. In fact I’d argue it was the last time Microsoft put refinement above new features too.

It was the first time we saw a workstation OS suitable for home use (aside perhaps BeOS but much as I love BeOS, NT was a more sophisticated engineering feat).

Windows 2000 was the first time a windows release didn’t double the system requirements. A trend that then continued again right up until around 7/8.

Windows 2000 was rock solid. I only managed to crash it twice and one of those times was because I was playing around with an undocumented Windows API — so that really was my own fault.

Windows 2000 was the last time was unified UI across all of the OS management tools. Except for the font management which was still a 16-bit app. Microsoft have only gotten worse at this since too. It was also the prettiest too (but that’s entirely subjective).

Windows 2000 was the OS that shipped the most sane defaults. Though there was still some WTF moments like the terminal port being open. Since then though, I’m constantly fighting with Windows trying to dumb everything down.

Windows 2000 is what proved to the world that Microsoft could release a half decent OS that supports SMP and doesn’t require a DOS bootloader. It was a real game changer of an OS and released at the time when everything else on the market was garage too. Which just goes to demonstrate just how much of a game changer it was.

It was, in my opinion, not only the first Microsoft OS that didn’t completely suck in every conceivable way. But arguably the only good OS they’ve ever released because everything since has been fraught with compromises. Including 7.

XP pre-SP2 was basically an uglier 2000 with twice the CPU and memory footprint. After SP2 XP grew into its own entirely. But by that point desktop Linux was good enough to run as my primary OS.

Edit: the opinions here are both my own, and my professional experience managing desktop and server IT infrastructures for small businesses at that time. And at that time, Windows 2000 changed everything. If 7 hadn’t been released then Microsoft could have kept supporting XP and most people would have been perfectly happy. But if 2000 wasn’t released then Microsoft would have been in the same deep shit that Apple were with their repeated failed attempts at creating a successor to Mac OS prior to re-hiring Steve Jobs.