I think Windows 9x was peak Windows.
Everything is clear, you know what's a button and what's not. Information density is also high, which is a good thing on a computer screen.
But the main thing is that Windows 9x felt responsive. The Windows widgets felt solid and performant, while "modern" UWP apps feel clunky and prone to breakage. And don't even get me started on Electron.
Edit. See OP's previous article here, he managed to capture what I was trying to say in more details, with nice screenshots: https://movq.de/blog/postings/2026-06-16/0/POSTING-en.html
I find this take (from the guy who wrote the Windows task manager while at Microsoft) to be evenhanded.
> Windows "SUCKS": How I'd Fix it by a retired Microsoft Windows engineer.
Products have to change in a visible way so people know they're new.
I'd replace 9x by windows 2000. It was the only decent windows. 9x were BSOD crashfest, 2000 was stable as NT but without the enshittification of XP (ugly default themes, stuff above calling internet services with zero value).
I think what you describe as responsive are 2 things:
1. absence of animations. I don't know about windows but on linux DE you can disable them, it feels snappier but more raw and I think most people still prefer the animations.
2. Visual and audio clues. Back in the days we were on spinning disks so anytime you'd click on somethimg you would hear the disk moaning in pain and see that disk led blinking. You knew that something was happening, even if it took a long time. When SSD were introduced, everything became instant and silent for a few years, it was pure bliss. Then over the last decade apps continued growing and growing in size and as fast as they were SSDs and NVME started not feeling that fast because so much stuff had to be loaded into memory. Nowadays many apps are still starting much faster than before but the biggest one still take a substantial time. Worse, we have lost all visual and audio clues that something is happening.
I think Windows 9x was peak Windows.
I'd choose XP instead. People disputing the performance maybe should consider the hardware at that time. Real problem with 9x was low-level stability. Juggling with compatibility was difficult, file access comes to mind, it was a kludge. It was possible but hard to maintain the system in a sensible state.
XP was the first to bring NT architecture to desktop. It was a huge success. Many despised the colorful UI, I actually like it. They started moving things around, but annoyances were fixable. Microsoft has adopted more of a "my way or the highway" attitude since.
This is because back in the 90s GUI development was still driven by hard research, not by "emotions" (e.g. actually sitting very diverse groups of people in front of computers, asking them to perform specific tasks and then analysing where exactly they got stuck or became confused).
IIRC this golden era of GUI research fell apart once people started to call themselves "UX designers".
> Everything is clear, you know what's a button and what's not. Information density is also high, which is a good thing on a computer screen.
I would say information density was too high. All those always-on indicators: 3D scrollbars, buttons, etc. create a very busy picture. Today's interfaces are much cleaner which comes at a price of less information and hence, more ambiguity, but I for would rather pay that price than go back.
One problem I see is that while the UI itself has been simplified, incidental complexity has crept in other ways. Most importantly, the OSes themselves as software systems have clearly grown ponderous and unwieldy so that today they are more bugs and more of those bugs can be subtle and surprising. Also, there is less uniformity in UX across apps (and UI frameworks).
Windows 9x did not feel ‘performant’. This is a false memory people seem to have.
Spinning rust hard drives were slow. It took ages to launch a program - loading screens typically had time to display a progress bar and a series of notes about what they were up to - ‘loading extensions’, ‘reticulating splines’, etc. Word would stall whenever it was autosaving. Carrying out an operation like spell checking or doing a find across a whole document or getting a word count took time.
Remember windows used to have an hourglass cursor? You used to have to watch that thing flip and empty multiple times when doing things like emptying the recycle bin.
Windows 9x was typically not running on a permanently networked computer. The computer wasn’t running a bunch of background network tasks like checking for updates or polling your email - generally it was just being slow because it could barely cope with running more than one program at once.