XP was fine. 2000 was good. Nobody pines for Windows ME. People said those things and they meant it. Windows 8-11 feel pretty bad, overall. 7 was okay.

The Windows 2000 UI was not "good," at least compared to what they have today.

Personally, I consider 2000 the version where windows peaked. They did add some good things since then, but did more damage than good in total.

So as we differ this clearly in opinion: What makes you appreciate the windows UI more today?

Adding a search to the start menu is huge and completely changed how I use it -- I almost never do anything besides hit the Windows key and start typing a search query. Besides that, the way nested menus worked was frustrating and I'd frequently waste time doing things I didn't intend trying to navigate them.

That explains it. I use win+R (the hotkey for run) the same way since I think win95.

When I search the start menu, it does the weirdest things, e.g searching notepad via bing instead of starting it, or preferring the uninstaller above the real program. So I learned that the start menu is basically broken for search, and became harder to use as a menu. I mostly abandoned it.

Meanwhile, the gui widgets, built in windows and control panels became much worse and dumbed down. It pretends to be a helpfull assistant, but behaves more like an arrogant drunk. I want to do some work on the machine, not be told about some experience it really wants to shove in my face.

Well, the difference is Windows + R I would need an exact command and the search bar I don't. I share some of your frustrations about the relevance of the top result but still, partial matches are important to me.

What they have today is an UI disaster: cannot tell which window is active, scrollbars are so 90s - nobody cares about them, settings would make Google proud - one cannot know if the text is only a description or it starts a config dialog, 1 px window border - good luck resizing on a 4k monitor, gray on gray, titlebar highjacking, hard drive hidden in explorer beside virtual folders etc.

XP was fine because you could throw it into 2000 mode, though looking back the fisher-price UI was just the UI.

Windows Vista wasn't terrible if you had a beefy machine and well-supported hardware. 7 was basically Vista but with newer machines and better hardware support. 8+ has been meh.

IMO, Vista was actually the best-looking Windows of all time.

Heck I still say that about Windows 2000. Clean, minimal interface, with all the power options easily available.