According to South Park the movie, Windows 98
After 95.
Vista I think
I agree on the ads and bundled services, but the "windows is slow" stuff is horseshit. A tight build of Linux boots more quickly no doubt, but a fresh Win10 or 11 install, even with bloat, is up in under 30 seconds, and runs swiftly out of the box. This isn't "slow" by any definition.
Again, let's hate the other shit, let's hate on that together.
Windows Vista was the start in my eyes. XP (pro) was amazing. And then Vista came out and it broke a lot of things. Security was garbage, applications would constantly lose root files
Vista only lasted 2 years before they went back and turned it into Windows 7 with a few small tweaks, but more or less the exact same thing
98, XP, 7, 10: Good.
ME, Vista, 8, 11: Bad.
It's Star Trek Movies all over again. We just need to hang on for Windows 12.
98 still had plenty of jank, but it was worlds better than 95. I would add 3/3.11 to the "good" list if only because that was basically the only other option for a lot of people and it did what it needed to. I don't recall personally seeing windows 1 or 2.
edit: I guess I could throw NT mostly into the good section, but I mostly just did tech support for it rather than using it.
probably 8 or 10
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