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Chain of Fools : Upgrading through every version of windows (HQ)

TheRasteri
Demos
YouTube
2 HN users recommended this demo2 months2011–2021 score 2
Years with an HN recommendation, 2007–2026

HN cites it as evidence of Microsoft's backward compatibility and of upgrade engineering done well.

TheRasteri installs MS-DOS and Windows 1.0, then upgrades in place through nearly every Windows version up to Windows 7, checking which programs survive. Even Doom from 1993 still runs at the end.

“It's a sight to behold.” (HN, 2011)

2 recommendations · 10 citations · Demos

12 Hacker News comments

From the HN archive; up to 20 kept per video, favoring different commenters. Recommendations first.

@alexsb92 Mar 2013 Recommends
on HN thread Building Photoshop 1.0
Read more
> I often think about how incredibly inefficient modern software is given that we've had roughly the same level of productivity software ability (with varying levels of usability) for a few decades now. I distinctly remember my NT4 system of the late 90's, and how it was roughly as productive as my current machine, and I wonder just how much cruft is inside modern operating systems and applications. As a fellow young person (probably even younger than you), I remember watching this video [this video] two years ago when it came out and I remember gaining quite an appreciation for all the work put in over time in Windows and the complexity that it probably brings.
Gave appreciation for the work and complexity in Windows

Citations, criticism and jokes

@trafficlight Nov 2011 Cites it
on HN thread How Can Anyone Still Hate Bill Gates?
Reminded me of the video where a guy did a fresh install of Windows 1.0 and upgraded all the way to Windows 7. An amazing amount of programs still ran by the time he got to 7. [this video]
Windows 1.0 upgraded to 7 with programs still running
@ayi Jun 2012 Cites it
on HN thread PHP: the quiet powerhouse
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PHP's problem is it's soul. I will make an analogy about this. My analogy will be local, but i will explain it so you can understand. PHP is my university, Gazi University. It first established in 1926 as a Teacher Training Institute. Nobody knew that there will be a medical school or faculty of fine arts or even a faculty of dentistry. 1926 was the third of our newly established Republic and we needed teachers. So, Teacher Training Institute was born. Our main campus is very small. Law School or dentistry school is not in the campus. Because, as i said, nobody knew we need them in 1926. Ruby, C# and many other languages are METU: Middle East Technical University. METU was designed as a university. So, they got a gigantic land in Ankara (capital city of Turkey). They build all their building in there. Back to the PHP: PHP was born to solve one problem. Just one problem. When they got another problem, they solved it and added the function or implementation in the language. PHP is not designed at desk, it was not "feature-complete" at version 1.0. It's still getting more mature as version numbers increase. For example we get "traits" in 5.4. PHP is also Windows too (both Microsoft and PHP in a HN comment :) The most un-loved things in this community). Remember the video which a guy installs Windows 1.0 and successfully upgrade it to every version of windows with all his data and programs up to Windows 7? even doom from 1993 works! ( [this video] ) PHP is like Windows. I know the "pa
Windows 1.0 upgrade to 7 used as analogy for PHP
@cooldeal Sep 2012 Cites it
on HN thread Developer interest in Windows 8 is stagnant, new line of worry for Microsoft
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Funny you say that, because Microsoft's software problems are often attributed to bending over backwards to be backward compatible while other vendors like Apple quickly kills compatibility with almost ever release, with even point releases. Take this game bundled with Windows 95. ftp://ftp.microsoft.com/deskapps/games/public/AAS/Hover.exe It runs even on Windows 8. Upgrading from Windows 1.0 to Windows 7. [this video] As I said in another comment, I still see some ASP and Visual Basic usage even after all these years, those applications are still supported in Windows 8 and Windows Server 2012. Microsoft stopped making new versions because it wanted to move on to better technology. Want to take a poll on HN about what developers think of Visual Basic and Classic ASP? A case of damned if they do, damned if they don't.
Evidence of Microsoft's backward compatibility
@RKearney Sep 2013 Cites it
on HN thread ReactOS: Rebuilding Microsoft Windows from the ground up, fully open-source
I don't know about you, but I have much, much better luck running executables under Windows than say Linux or OS X. Microsoft puts a ton of work into keeping backwards compatibility. You can watch the YouTube Video[0] of someone upgrading through every Windows version (well, most?). OS X users have to figure out if they need that Intel or PPC binary, or maybe just the larger universal one and call it a day. Then there's not being able to run any of their older PPC-only apps once Apple removed Rosetta from OS X. [0] [this video]
Someone upgrading through nearly every Windows version
@candl Oct 2013 Cites it
on HN thread Ubuntu 13.10 (Saucy Salamander)
Here's a video of a continuous upgrade from ms-dos through every windows version all up to windows 7 (a timespan of ~20 years) that proves it's possible. [this video]
Continuous upgrade from MS-DOS to Windows 7 proves it's possible
@rogerbinns Mar 2015 Cites it
on HN thread Intel blames $1B revenue hit on Windows XP's stubborn grip
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They neglected to mention just how hard it is to "upgrade" from XP. If you want to install Windows 7 or 8 then it will only do a clean install. You have to figure out all the apps you have installed, install media, receipts/keys/vendor site logins, do the "upgrade", and then play system administrator for a long time. Approximately no one has backups, so all that needs to be sorted out too, as well as doing a restoration. Then new UI has to be learned. Nothing is where it was. Various apps probably had to be upgraded too, and they'll have new UI to learn too. Then they have to figure out system administration - how do you do updates, make the funky printer work, deal with anti-virus. I didn't even mention figuring out that whole 32 versus 64 bits thing either. The time, effort and money involved, especially for small businesses/organisations and individuals is daunting, not to mention a distraction from what their actual business is. By far the easiest thing for them is to do nothing. Microsoft really screwed up by not making a good upgrade process. They know how to do it, and did it in the past. [this video]
Shows Microsoft knew how to do upgrades in the past
@b4ux1t3 Aug 2017 Cites it
on HN thread An Argument for Why Windows Will Go Open Source
No, it really doesn't. Windows has had backwards compatibility as a huge priority for a long time, often to their detriment. You can literally update a machine from Windows 3.1 to windows 10, and programs written for Windows 3.1 will still work.[1] [1]: [this video] EDIT: TO be clear, this is a video of upgrading to Windows 7, and there is a direct upgrade path to 10 from 7. Also, as per another user's reply, this doesn't hold true for 64-bit. However, that doesn't change the fact that Wine doesn't and really can't run win32 better than win32 does.
Shows Windows 3.1 programs surviving upgrades to Windows 7
@kirb Sep 2021 Cites it
on HN thread Please don’t theme our apps
Read more
Adding onto your point, I’m reminded of the video “Chain of Fools”, where a machine is upgraded from Windows 1.0 all the way through to Windows 8. Once he reaches XP, the theme he configured back in one of the first Windows versions just disappears and gets overridden with XP’s defaults. Then it happens again and again for every version since then, despite the guy changing the theme back to his custom one before each upgrade. [this video] So the phenomenon really started with Microsoft themselves. Sure, the more muted dialog backgrounds and vibrant foreground elements introduced since XP look far better than the Win95-esque greys, but I’m sure people who created their own themes (probably due to disability like color blindness) like their colors better than Microsoft’s.
Custom theme gets overridden at each Windows upgrade

Video list and Hacker News comment labels from HackerTube (prompted by @karpathy), released under ODC-By 1.0, built on the open-index/hacker-news archive. Hacker News data is provided by Y Combinator; comments remain the work of their authors. Video titles, channel names and thumbnails belong to their creators and are shown via YouTube. HackerTube Watch is an unofficial edition. Data export of 2026-10-31.

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