Recently, our sister website, PCMag, celebrated Microsoft’s 50th anniversary by sharing a visual history of Windows client OSes over the decades, starting with Windows 1.0 and going up to Windows 11.
Image source: PCMag
What are your best (or worst) memories of Windows?
Do you have any fond or not-so-fond memories of Windows from its 35+ years of existence?
Off the top of my head, here are a few notable personal Windows moments:
-
Windows 3.1 - I still remember when my dad’s friend taught me how to play Minesweeper on our 386 Compaq with a VGA monitor.
-
Windows 98 - When I hooked up my brand-new Quantex computer at college (with a GIANT and HEAVY 19" CRT monitor), I quickly discovered that you could download MP3s in 3 seconds over the school network vs. 30 minutes over dial-up. We were all in awe.
-
Windows XP Media Center - Before the streaming revolution, I set up a low-profile computer (that fit in our TV cabinet) to record Live TV and play shows on demand at any time. I felt like I was living in the future!
Share your Windows memories in the comments!
33 Spice ups
bcrooms
(bcrooms)
2
Windows ME. No further explanation needed… 
23 Spice ups
I remember going from 3.1 to 3.11. That was all the rave back then.
Worst memories were those pesky BSOD and then trying to determine what driver was causing them. They seem to be a thing of the past.
12 Spice ups
Hmm… Jezz Ball, if I am remembering right. It came with some Windows version for some brand of computers, and I had a lot of fun trying to catch the ball in increasingly small boxes.
10 Spice ups
cag16
(CAG16)
5
The excitement around Windows 95 is something I will never forget. The growing interest at the time in computers and the dawn of the Internet created this atmosphere of endless possibilities. Then Win98 came out and I remember liking the updated UI better, but not the instability of the first release . Win98SE fixed some of that, iirc. As already stated, we won’t talk about ME. Then XP came out, and that was my favorite for a long time, until Win7 was released. That is still my most favorite version of Windows to date. Every other release of Windows since then has been nothing but disappointments. Win11 has really pushed me over to Mac and Linux going forward.
17 Spice ups
ajason
(aJason)
6
Oddly, I had Win 3.1 (or 3.11, I don’t really remember,) and never used it. It came with my PC and also had a Win95 upgrade, so I immediately upgraded to Win95. From there, I upgraded to Win98.
I had a 486 DX2 PC. I don’t remember how much RAM, but I had around a 500 MB drive. To gain space, I compressed the drive. Back then I tended to reinstall Windows about once a year or so since the HDD would get full. If I recall, to format the drive, I had to uncompress the drive first. I think that install took me between 8 to 10 hours.
6 Spice ups
The first edition I recall using on a computer of my own was v3.1 on a handed down Tandy 2100. We had its sibling v3.11 for Workgroups at school. Before that it was DOS.
My uncle bought a complete NEC system sometime in the late 1990s. It was no doubt pretty expensive at the time but he was notoriously (over)protective of the whole thing, even going so far as to keep it covered with a sheet when not in use. It came loaded with Win95 and a game called “Hover!” that we were allowed to play occasionally. Funny to think that it’s no doubt been recycled or sitting in a landfill for close to 30 years now.
6 Spice ups
tb33t
(TB33T)
8
I loved Win XP, since that’s when I started getting into building my own PCs. I can still remember attaching the molex connectors and finally getting that XP boot up screen. A few years later I decided to buy a Gateway that came with Vista. It looked cool but chewed up what little memory my computer had. It was tough. Lesson learned to do some research before just leaning into an OS I had no knowledge of.
7 Spice ups
ajason
(aJason)
9
I have forgotten about Hover! I probably haven’t thought about it for thirty years.
I do have Space Cadet pinball on my phone though…
7 Spice ups
All the hype with Windows 95 was something else. It was an exciting time to be a geek lol
I remember being in school and working in Windows NT, then the teacher showing us a demo version of Windows 2000 Server. One of the things that blew many a mind was the whole PDC and BDC going bye bye and just being a DC.
Really funny that 25 years later, I still have to correct individuals that still refer them as PDCs. Literally did this a few weeks ago.
8 Spice ups
I worked at a university when XP came out (not officially in IT, but the guy who people came to with computer issues). The first computer with it installed was automatically determined to be hazardous by Network Operations and shut down the internet on the floor for 2 days. I didn’t like or trust XP for a LONG time!
5 Spice ups
Best & Worst Windows Memory? …
Out Of Bounds Port Punting 
5 Spice ups
Slava
(Slava)
16
After using MS DOS 5.0 getting my hands on a Windows 3.1 was something out of this world.
12 Spice ups
I’ve been using computers ever since the early 80’s and started with DOS V2.11. I loved it when a new version of DOS was released and it allowed extra functionality. As windows came mainstream I’ve been through them all. The worst version which I used for a day and then removed it from my system was Windows 8. Whoever thought that was a good idea must have had a screw loose. Even Windows ME was better than that!
11 Spice ups
mfaflik
(MichalBorg)
18
You must have not seen ME
4 Spice ups
ME wasn’t ALL bad. I remember copying defrag.exe from it on to Windows 98 machines, because it was faster than the version they had 
6 Spice ups
I remember building my own computer and we had a full version of Windows 95. I installed that and we had upgrades for 98 and ME. I upgraded to 98 and ME. ME sucked as many will recall and I went back to 98 until a buddy gave me a copy of Windows NT. I remember overclocking an AMD processor with the utility that came with it. I think I was on 98 at the time.
9 Spice ups
