Oldest GUI application that still runs on Windows 11

(blog.enlyth.com)

195 points | by enlyth 4 hours ago

21 comments

  • sedatk 1 minute ago
    I remember having installed Win32s package to our Windows for Workgroups 3.11 machines at Osmangazi University in 1995. The idea was that Windows, as a 16-bit operating system, could run a subset of Win32 apps that were compatible with the Win32s API surface. However, the release of Windows 95 had almost immediately made it obsolete. I'm sure it was useful in certain scenarios, but our only win was Freecell. :)
  • drnick1 2 hours ago
    I deplore the day we lost the menu bar and replaced it with "mobile first" designs. The desktop UI was perfected around the time of Windows 95 and has gotten worse with every iteration since then. That, and the increased reliance on non-native frameworks and libraries instead of working with directly with the Windows API in C.
    • cowlevel 1 hour ago
      Android used to have a dedicated menu key that would always bring up a menu. It was removed to chase Apple's 100% screen design.
      • andechs 26 minutes ago
        Long-press and the ••• menu in the overflow is a far superior UI paradigm than having a purpose built menu button.

        90% of the time, even in Android that was pre-Honeycomb, the menu ended up just showing what would have been in the overflow anyways.

        Android really did end up doing a lot better on the UX side that iOS with the contextual action bar and long-press to select. The idea of selection mode on iOS is still a weird process, and it's been mostly worked around since with higher PPI screens and touch sensors, instead doing a small area to "select" items on iOS

      • frantathefranta 1 hour ago
        Just got nostalgic about the 4 hardware buttons on my Sony Xperia Play: back-home-context(option)-search.

        Still the best navigable phone I had when coupled with the Nova Launcher gestures.

    • bcvvvy 2 hours ago
      I am fairly bothered about that but the one that really gets to me is the inconsistency of user interfaces across applications.

      This precisely coincides with the web developers being allowed to wrap stuff into "apps" in Electron and the like.

      • ChrisClark 1 hour ago
        It's been that way forever, did you forget about the Borland buttons? Colorful icons on them, much bigger, different shading.
        • layer8 22 minutes ago
          They had a different look, but usage and UI conventions including keyboard navigation worked basically the same. Since the mixing of mobile and desktop with web technology, it’s the Wild West.
        • gmueckl 57 minutes ago
          But they were not too far removed from how the standard Windows buttons looked. Office had its own look in a lot of ways back then, e.g. with the extra handles on the toolbars.

          Now, if I take a couple of current applications, the differences are much bigger: from the top of my head, Explorer, Settings, Edge, Office, Steam, Spotify all have much more unique UIs.

    • anjel 28 minutes ago
      The war on scroll bars has gotten pretty senseless.
    • pjmlp 21 minutes ago
      Working directly with C API in Windows has not been a thing since Vista, as COM took the main role for API delivery.

      The Windows SDK samples like Hilo make use of C++ with COM.

    • okanat 1 hour ago
      Although I started with 98, I think Vista / 7 was the peak. It was user friendly enough for newbies but didn't sacrifice advanced controls. Just organized them better to bring focus to the more used parts.
      • larusso 0 minutes ago
        I used the Zune theme for windows XP which I really liked. I dreaded Vista because it was just a resource eater with all the effects turned on.

        https://www.softpedia.com/get/Desktop-Enhancements/Themes/Mi...

      • theandrewbailey 1 hour ago
        In terms of aesthetic, I love Windows 7-era Aero glass design (and to a lesser extent, Vista), but I also love the classic Windows 9x/2000 look. If I had to choose between the two, I'd go with Aero simply because of the start menu search bar.
      • Zarathustra30 36 minutes ago
        Maybe on the OS side. However, Vista coincided with the release of Office 2007. That release of Office introduced the dreaded Ribbon, which made functions much harder to find.
      • abhgh 1 hour ago
        I loved Windows Aero and the flip 3D view - the latter mostly because it looked so cool for that time!
        • LtWorf 56 minutes ago
          Oh you mean "ripping off compiz"?
          • someguyiguess 27 minutes ago
            I just learned that X Window System came out a year before the first Windows release. Interesting. Thanks for pointing out the compiz ripoff. It spurred me to look up the original release dates.
    • pavlov 1 hour ago
      Windows 95 was the last release that had serious user testing in controlled environments. (They were also cribbing lots of notes from NeXT, which helped.)

      Something fundamentally switched around 1998-2002 in how interface design was viewed and approached. I started my career in software as a design summer intern at a company that made a Windows “groupware” application in 1997. They took pride in following the platform’s guidelines and actually testing their designs with real users being videotaped trying to use it. The company’s UI design department was tiny, but employed both an industrial designer and a cognitive scientist.

      Five years later, everybody I met in UI design was a graphic designer who was drawing glossy website mockups in Photoshop. The elder lore of science-based UI design was completely lost when Web 2.0 happened and app designs became vibes-based. Even Apple couldn’t resist the tide. (Indeed Steve Jobs’s return to Apple in 1997 was a major contributor because he had developed a taste for user-hostile skeuomorphism like the brushed metal QuickTime Player.)

      • someguyiguess 25 minutes ago
        Skeumorphism is the opposite of user hostile. Flat design. Now THAT is user hostile.
    • dpark 2 hours ago
      > we lost the menu bar and replaced it with "mobile first" designs

      What does this mean? I use lots of apps that still have a menu bar.

      Some apps eschew it, like browsers, but not because they are “mobile first”, but because they are trying to maximize screen space.

      • Narishma 1 hour ago
        > but because they are trying to maximize screen space

        If that was the case they wouldn't put giant margins around every UI element and dead space everywhere.

      • drnick1 1 hour ago
        > Some apps eschew it, like browsers, but not because they are “mobile first”, but because they are trying to maximize screen space.

        I don't think this is true. If anything, we see more oversized buttons and empty space nowadays. It's as if developers forgot that PC users have keyboards and mice. Remember, display resolutions and monitors were a lot smaller back then, and making space count was arguably more important 20 years ago than it is today.

        • dpark 10 minutes ago
          Two things can both be true. An app can create more space around controls and get rid of the menu bar to save space.

          The space also really has nothing to do with “mobile first”. It’s for touch screens (and also modern aesthetic that avoids crowded controls).

          To be clear, I am not saying that all apps are optimizing for saving screen space. I was specifically talking about browsers, which are broadly optimized to give as much area as possible to the content.

      • breakwaterlabs 1 hour ago
        > they are trying to maximize screen space.

        Ironic to say on hackernews which shows massive whitespace in the margins-- and if I try to widen my tab sidebar it actually indents the margin rather than eating into it.

        One can look across the computing space as a whole and see that, it is surely not the case that we're "maximizing screen space".

        • LeFantome 52 minutes ago
          Totally agree. But this does not take away from his point that maximizing screen space is the motivation in Firefox. In fact, all you have done is demonstrate why they are driven to do so.
          • jrumbut 23 minutes ago
            Maximized screen space doesn't really benefit this site.

            The key element missing from this thread is that the Internet going from a text based to a multi-media (and increasingly video-centric) experience.

            A lot of Internet users, at this point, do as much reading on their phone or laptop as I do reading on my TV (almost none).

        • someguyiguess 24 minutes ago
          You think Hacker News’ design is new? It’s looked exactly the same since I started using it over a decade ago.
    • Grosvenor 1 hour ago
      The Desktop GUI was perfected with NeXTStep in 1990. Though some might say Smalltalk in 1984 (modulo some nice artwork and colours).

      We could even have unified desktop.mobile codebases, with different GUI layouts. 280 North's objective-J/Cappuccino proved this.

      IDK what we're even doing anymore.

      • NetMageSCW 1 hour ago
        The early Mac made huge functional improvements over the Smalltalk GUI, improvements still used today.
    • dragontamer 1 hour ago
      The Menu + quick access bar was good for developers but terrible for users, at least compared to the ribbon.

      Ribbon is absolutely an improvement for users but is more work for the XML layout and learning how to organize it.

      I'm rather convinced that Ribbon is still the best way to organize quick actions, show their shortcuts (Alt to see keyboard shortcuts), and also have enough text to describe all the buttons. But it'd be nice if it were easier to make good Ribbons.

      Menu was braindead easy, albeit through ancient process of .rc files and whatnot

      • thesuitonym 1 hour ago
        I'm just not sure why it has to be one or the other. Look at NeXTStep. They had a menu bar (or I guess a menu panel) and a ribbon, although that term didn't exist yet, and it was definitely not 100% there yet.
    • latexr 1 hour ago
      > The desktop UI was perfected around the time of Windows 95

      There’s no need to be hyperbolic or blinded by nostalgia. Yes, user interfaces have suffered several setbacks in the years since, but even if we concede every change was for the worse (they weren’t) it was by no means “perfected” and there was still plenty of area for improvement.

    • fellowniusmonk 1 hour ago
      I agree with you generally but I don't think desktop UI is remotely close to perfected. Unless you mean the desktop as a skeumorphic concept than maybe.

      I think we've actually completely stagnate on the human interaction side of OSes and only emacs has made any progress and then only for those willing to put the work in, not as a vanilla user ui.

    • excalibur 2 hours ago
      > The desktop UI was perfected around the time of Windows 95 and has gotten worse with every iteration since then.

      Well that can't be entirely true, the desktop experience on Windows 10 improved on Windows 8 by leaps and bounds.

      • john01dav 2 hours ago
        > Well that can't be entirely true, the desktop experience on Windows 10 improved on Windows 8 by leaps and bounds.

        In large part, windows 10's ui is more like that of windows 95 because it undid the changes away from the windows 95 paradigm that windows 8 did. Furthermore, those changes away from windows 95 in windows 8 were the exact kind of thing that might be called "mobile first".

      • MattPalmer1086 2 hours ago
        Haha, yes. It does not account for releases which made UX dramatically worse (win 8) which were then reverted to some extent.
      • layer8 18 minutes ago
        Only because Windows 8 was such a dramatic step back. Windows 7 is still better than Windows 10 in terms of UI.
      • nubinetwork 1 hour ago
        Not until they settle on one control panel.
      • Borg3 2 hours ago
        Are you nuts? Or wait.. you must be Gen Z then, never really used Win95.. If so, you cant make any statements in the subject.

        I still run Windows Classic GUI here, because its fast and confortable to use. Can you do better? Hmm, maybe. But im not conviced :)

        • PorciiVorbesc 2 hours ago
          >Are you nuts? Or wait.. you must be Gen Z then, never really used Win95.. If so, you cant make any statements in the subject.

          What a terrible attitude to have as a comment reply. I've been using Windows since Windows 95, meaning I have plenty of experience and some emotional attachment to it and I'm as millenial with knee pain as they get, so not Gen-Z, and I can't imagine going back to using W95 today productively in a non-ironic way.

          Windows 95 was perfect ... for what people did on computers back in 1995, not for what I do now in 2026 on the HW of today. May W95 rest in peace, but I'll take my modern OS for my moderns entertainment and productivity tasks on modern HW. There's no way in hell I'd want to go back to W95 even if that's what popped my cherry. People calming otherwise have rose tinted glasses and only remember the good parts of that era without the downsides.

          • Borg3 1 hour ago
            Can you tell me more? What are you doing that good old classic windows would be barely usable? Im really curious, because I was using corporate Win10 and hell, it was really driving me crazy. Good that there is Cygwin, so I could move most stuff there. Classic Windows just works, and if you care, you can even customize it.
            • PorciiVorbesc 1 hour ago
              >Can you tell me more? What are you doing that good old classic windows would be barely usable?

              In modern WIndows, from 7 onward, I can hit the meta key and type the first letters of the app I want to open, hit enter and boom, it's opened. I can mouse snap the two app windows side by side on my large monitor. I have 125% scaling so things don't look tiny on my 4k monitor.

              Win 95 had none of that, the only way to launch an app was via shortcuts on the desktop or navigating a long and tedious star menu tree, which was perfectly fine for 1995 since you had ~10 app on your PC and you used it sparingly, but is really shit UX if your PC has 50+ apps like in 2026 and you use it for half a day. "Classic windows" only makes sense if you also use your PC in a classic way like it's the 90's, with like 1-2 concurrent apps opened at once, instead of 10+ leaving them on for days/weeks.

              >Good that there is Cygwin, so I could move most stuff there.

              Cygwin is CLI, not UI, which is what we were talking about. Are your complaints about the Windows CLI or about UI, because those are different topics you seem to mix up?

              >Classic Windows just works, and if you care, you can even customize it.

              I can also customize modern Windows, at least in the ways I need it to be productive. Sure, you can't customize it anymore in the W95 way, such as having a Matrix screensaver or Rollercoaster Tycoon theme on it, but I don't need that anymore since I'm old now and don't have time for that anymore. If I want a short hit of nostalgia I boot up my vintage Windows XP machine, but that's not my daily driver.

              >Im really curious, because I was using corporate Win10 and hell, it was really driving me crazy.

              If Win10 was driving you crazy, then "classic windows" would also drive you crazy even harder because it doesn't have any QoL over Win10. Please explain yourself here what you mean since you seem to be contradicting yourself. Or are you only talking about your limited corporate windows experience and and not what you can do as an admin on "home" windows?

              • jpc0 1 hour ago
                > In modern WIndows, from 7 onward, I can hit the meta key and type the first letters of the app I want to open, hit enter and boom, it's opened.

                I mean in theory I can also do that on my Win 11 machine... In practice if I actually performed those exact steps I will probably have edge open up with a web search of the letters I typed.

                The amount of times I actually have to use the now even less user friendly way of finding an app in the start menu regardless is infuriating, give me both, a star menu that is deterministic and a search that works...

                Just because I want the older stuff does not mean I have to give up some of the newer stuff.

                • PorciiVorbesc 1 hour ago
                  > In practice if I actually performed those exact steps I will probably have edge open up with a web search of the letters I typed.

                  Not for me since I disabled web search feature of the start menu, but I get what you mean. I still prefer this option than being limited by the Win95 way. I always have 10+ apps opened at once. Having to manually launch them via the menu tree every time I boot up my OS would be a nightmare. This wasn't an issue in Win95 because I only had 16mb of RAM so I only launched one or two apps simultaneously, like for example MS Word for a school project and Winamp for listening to music while working and that's it. The kind of multitasking people do today without even thinking (50+ Chrome tabs, IDEs, Discord, Signal, Spotify, Steam, WSL, Plex, etc) was unheard of in Win95.

                  >Just because I want the older stuff

                  Yes, but you failed to explain exactly what "old stuff" UI did Win95 had that you don't have today and really need? You can still launch apps via the desktop shortcuts or the tedious start-menu tree view in Modern Windows as well like it's 1995, if that's what you miss from Win95, nobody forces you to use the broken search feature you dislike of modern windows.

        • thesdev 2 hours ago
          I think they were referring to the latter part (downhill ever since) and not the former (win 95 is the best).

          How are you running the classic GUI?

          • Borg3 1 hour ago
            Im still running Win2003 here, hence classic GUI (Win2000 like). Works like a charm :) I do some hacking (programing, reverse engineering) and playing games (old of course) on it.
        • ChrisClark 1 hour ago
          Typical insulting boomer reply. Personal attacks, against the rules, and nothing useful added to the discussion. And the guy you insulted isn't even Gen Z...
      • theandrewbailey 1 hour ago
        I can't tell if this is sarcasm. Windows 8 is a very low bar in terms of desktop UI. It was universally panned as a regression.
  • mattbee 1 hour ago
    I just resurrected a 90s kids CD-ROM game that shipped for Windows 3.1 - https://github.com/matthewbloch/orlys-draw-a-story-fixes

    The finished patch DLL ended up being a tour of the stuff that broke.

    The game did launch on Windows 11 but the main issue was that the 8-bit pre-DirectDraw behaviour was broken - for 256 colour screens, Windows 11 resolvesld palette indices only once, but the game relies on being able to change the palette for fades etc. Most of the screeen ended up black, but you could see the animated parts just fine.

    So most of fix ended up being to hook every draw call and implement a virtual GDI that acted like a graphics card of the day.

    There was a 32-bit disc space check that overflowed, a couple of use-after-free crashes and some racey threading calls that can't have been tested on a machine with 2 CPUs.

    Backwards compatibility from Microsoft was almost all there, and probably would have kept Orly running for a couple of subsequent Windows releases. But it relies on a developer meeting them half-way, it's not an emulation layer.

  • dofm 3 hours ago
    > At the time of this post, that’s a 33 years and 8 months old application,

    Pointing this out without a trigger warning is just rude ;-)

    Some of us are older than we think, yo.

    • suzzer99 1 hour ago
      I helped develop a web app used by major drug companies in 2001 that's still in use as far as I can tell. Marvel at the Dreamweaver-enabled design: https://resultview.q2labsolutions.com/resultview/logon/logon...
      • dofm 1 hour ago
        :-) Nice.

        The oldest web app code of my own that I still maintain/evolve turned 20 this year, so yours is older than mine. I think it's largely a Ship of Theseus at this point, though I did just remove some code the other day that was absolutely untouched since 2008.

  • tgtweak 1 hour ago
    I'm reminded of this amusing and brilliant post: https://blog.hiler.eu/win32-the-only-stable-abi/
  • capnjngl 2 hours ago
    Speaking of FreeCell, a couple weeks ago I was visiting my 95yr-old grandmother and noticed she still plays oldschool FreeCell, specifically a variant that's really hard to track down now called FreeCell Pro [https://cards.fandom.com/wiki/FreeCell_Pro]

    It inspired a weekend project. I always liked that you could swap the card backs in OG FreeCell and play with different "themed" decks, so I vibecoded something a little more modern. I got carried away and added a roguelite mode too (yeah I know how "Roguelite FreeCell" sounds). Anyway, it's free to play on the web, no ads: [https://freecellworlds.com/]

    • ramses0 2 hours ago
      Solitaire's Journey: https://en.wikipedia.org/wiki/Solitaire%27s_Journey

      Basically a 1992 rogue-lite where each room is a different solitaire game. eg: front parlor == clock solitaire, first bedroom == regular solitaire, upstairs is blocked by freecell, etc...

      Screenshots: https://www.mobygames.com/game/1986/solitaires-journey/scree...

      It's a fairly rich concept, you have a ton of different gameplay bound together by a very loose plot/quest mechanisms (eg: blue key == blue door ; boss == win 2 games of solitaire).

      Definitely worth sharing if you've got some solitaire fans in your life!

      • capnjngl 25 minutes ago
        Wow this is amazing! I love this bit from the Wikipedia article:

        "In 1996, Computer Gaming World declared Solitaire's Journey the 72nd-best computer game ever released."

        The bar has moved up a tad I think :D

    • bibstha 59 minutes ago
      Is there a but or maybe I don't know the rules. Sometimes I can't put a long sequence J 10 9 8 7 ... on a Q
      • capnjngl 28 minutes ago
        Yeah classic FreeCell only lets you move one card at a time. No stacks. A lot of FreeCell implementations have a QoL feature that let you move stacks if there's enough free cells or empty columns to allow the move.
  • xnx 1 hour ago
    Along these lines, I'm always amused with the videos (e.g. https://www.youtube.com/watch?v=C8CIhCTVyqQ) showing you can update a [virtual] device from Windows 3.1 to Windows 11.
  • andai 1 hour ago
    EasyToon (from 1998, I believe, built for Windows 95) runs on Windows 11. One of my favorite pieces of software.

    It's a thing for making little black and white animations. (With GIF export.)

    It was popular in the early 2000s and there was a subculture around it on animation forums.

    English version (hey, still online!):

    https://www.superfundungeonrun.com/easytoon/

    Original version (Japanese, w/ screenshots):

    https://web.archive.org/web/20020111185602/http://www.radium...

    There's also a forked version on a French website (also available in English) with some extra features. But I like to keep it simple :)

    https://www.flat2d.com/easytoon.html

  • lolpanda 2 hours ago
    In 2026 does it still make sense to build new Windows app using Win32 API? I was building a simple image viewer similar to QuickLook on Mac using Win32. I found it's very responsive. The code is less readable compared to React. For me Win32 is a good option if the UI state machine is simple enough.
    • Scharkenberg 12 minutes ago
      While Win32 tends to deliver the most resource-efficient and responsive apps if the complexity is not high, I have settled on the latest .NET + C# + Windows App SDK / WinUI 3. Making an app look good and fit into the modern Windows look is extremely hard with Win32 C/C++ and writing and maintaining it requires energy that I'd rather spend elsewhere. Besides, modern frameworks are making great strides in speed, efficiency and QoL features. .NET 11 is full of optimizations, for example.
    • okanat 1 hour ago
      I think the sweet spot is WPF or actaully its FOSS version: AvaloniaUI. It is high level enough to be cross-platform and not stupidly verbose, however it is rather light pn resources. However, Win32 still wins in absolute minimalism.
    • keithnz 1 hour ago
      yeah, it's still pretty good for a lot of things. I've found with AI it's now super easy to do native win32 apps really easily. It used to be doing all the plumbing was a PITA. There were wrappers to make it easier, but now you can do it directly. It means you get super performant, tiny binaries, that start instantly. Like windows should be. However, at home I've moved to linux a while back so way less useful to me now, though works fine with WINE. I still use it to make little utilities for work though.
    • adzm 1 hour ago
      Win32 API is great and responsive; ATL/WTL (and MFC) are still very useful abstractions with little cost. The biggest pain point is having to handle a lot of things manually, like DPI awareness (and themed controls). Even things like Emoji and other modern text features are not available through GDI and require DirectWrite iirc. Still, I'm surprised how useful it manages to be regardless how old it is.
    • chuckadams 2 hours ago
      Unless your name is Raymond Chen, you probably want to at least use ATL/MFC, which are frozen but still supported. Me, I'd take Qt any day, or wxWidgets if I wanted to go minimal.
    • NetMageSCW 51 minutes ago
      I would say WinForms in C# is still the best today.
    • the__alchemist 2 hours ago
      I wouldn't, because I do not think we should put up barriers in our application between OSs (Nor have to maintain separate UI code bases for each OS you think might use it). So I use cross-platform kits. There are compromises, but I don't care about the looks native qualification compared to works anywhere. Yes, the software looks like an EGUI app (etc. Substitute Qt), instead of Looks native, but I appreciate how I'm not setting up barriers between OSs or making extra work.
      • NetMageSCW 53 minutes ago
        So instead you are creating a bad UI for all of your users. That’s very Java application (or perhaps Electron these days) of you, but seems like a poor trade-off to me.
      • Doohickey-d 1 hour ago
        These days, with LLM assisted development, with relatively simple GUIs, I would go towards platform native GUIs per platform. And then all the shared business logic goes in a shared "core", with the GUIs only serving as "dumb" inputs and outputs, with all business logic shared between them.

        LLMs are quite good at tedious tasks such as keeping multiple GUIs in different languages in sync with each other.

        • Rohansi 6 minutes ago
          You still need to test all of those separate GUIs though so it's still costing more.

          You also generally don't want them to actually be in sync because there are actual UX differences between platforms that you need to align with to really be native. If you don't follow that then what's the point?

      • floydnoel 1 hour ago
        I couldn’t disagree more, when it comes to UIs. They should match the platform they are being used on. Cross-platform always produces a very sub-par experience. But us developers tend to care primarily about what makes development easiest for us.
        • Rohansi 37 minutes ago
          Not everyone has the resources to build five or six different UIs.
        • the__alchemist 1 hour ago
          What does this mean in practice for software you write? What OSes to you build it for, and what OS or GUI-specific conventions to you follow which don't apply to others?
      • jen20 2 hours ago
        I also don't care how if things _look_ native, I care if the work like a native app. For example, on the rare occasions I touch Windows, I expect standard keyboard shortcuts to work. On macOS, I expect full integration with the accessibility frameworks and OS affordances like services.

        A lowest common denominator idea of "everywhere" is just not that useful.

    • jim180 2 hours ago
      I am having a blast with AI + C + WinAPI. The responsiveness of WinAPI is awesome
    • toast0 2 hours ago
      I mean, if I was building a windows app, I would. Microsoft always tries to convince people to stop using it, but Win32 keeps working.

      If Microsoft ever makes something that actually meets all the needs that Win32 addresses, they'll probably build a compat layer and a) your win32 code will still work in compat mode, b) that new thing may be worth targeting.

  • mijowi 3 hours ago
    I often think old GUIs have a nice, functional look to them. This one is no exception. I notice (what I assume is) the shuffle toggle looks unfamiliar. This is from way back before that UI became a convention! I see the repeat icon has stuck around. So interesting!
    • weinzierl 3 hours ago
      Microsoft (and Apple) poured a ton of money into usability research in the early 90s and it showed. I vaguely remember the story through how many versions of the trash icon Microsoft went for Windows 95 to get it right.

      For me it was a bit sad to see the mad and creative UX world of the homecomputer era being bulldozed over with the minimalist uniform results of the scientific usability research.

      Little did I know that a mere quarter century later we are back were we once started and everyone as clueless as we were in the 90s goes overboard everywhere as if there was no tomorrow.

      Yeah, and it sadly makes me miss the nicely ordered and easily usable world - I'm gettin' old I guess.

    • elxr 3 hours ago
      Functionality isn't hidden and buttons looked like buttons (instead of the modern trend of having unstyled text or tiny icons having a 50-50 chance of being a button).
      • dawnerd 2 hours ago
        The flat design trend really confused me. It really took off when high resolution screens started getting popular too, really made no sense. Wish we'd bring back Skeuomorphic design. Bring back that wood grain and metal textures. Bring back the fun UI's and app themes. Bring back real buttons!
    • bluedino 2 hours ago
      There are a couple versions of the Windows CD player here (along with other operating systems)

      https://guidebookgallery.org/screenshots/cdplayer/

      I always liked the look of the more complicated ones like this:

      https://ctrl-alt-rees.com/2021-09-29-media-rack-download-win...

  • kidel001 1 hour ago
    I like that we are amazed by this. And yet all of my books from 34 years ago open up just fine (without cheating, no book opening emulator required!). I can even open a book on my shelf from 1896 without emulation. Not trying to troll too hard but I do think it is shocking how accustomed we've gotten to zero backwards compatibility in the world of software.
    • anthonypasq 52 minutes ago
      a better example would be whether you could put a train from 1845 on a modern track, or fire a musketball from an M16
      • wildzzz 7 minutes ago
        Many militaries are still buying rifles that chamber a cartridge introduced in 1891 (7.62x54mmR). I'd argue a cartridge initially developed for a long bolt action rifle (Mosin-Nagant) that can now be fired out of a variant of a AK-patten select-fire bull-pup (Vepr) fits the analogy.
      • jeroenhd 36 minutes ago
        If you live in a country or region where the gauge didn't change, you can put a 1845 train on a modern track just fine. If the gauge did change, you'll need a train from another country. Standard Gauge was first applied in 1825 after all.
      • Barrin92 40 minutes ago
        >whether you could put a train from 1845 on a modern track

        you can do that, in fact I know that Austria still has a mid 19th century train in regular operation (https://de.wikipedia.org/wiki/SB_alt_23)

        if you're looking for commuter trains a lot of early 20th century ones still operate around the world.

    • eahhn 33 minutes ago
      I guess this is one of those proverbial “I had to create an account to comment” messages:

      https://m.youtube.com/watch?v=pQHX-SjgQvQ

    • andai 1 hour ago
      https://xkcd.com/1909/

      It is amazing, though. Wintel is basically a Matryoshka doll (Russian nesting dolls), where each version contains all the previous versions. (Just look at how a PC boots up!)

      The dedication to compatibility is commendable, and you don't really see it on the other OS's. On that note, this is one of my favorite articles:

      Win32 is the only stable ABI on Linux

      https://blog.hiler.eu/win32-the-only-stable-abi/

      I think that's very funny. Speaking of which, EasyToon also runs in WINE, of course :)

      https://news.ycombinator.com/item?id=50250809

  • MisterTea 1 hour ago
    > And although using otvdm does feel like cheating, I thought it was cool enough to include in this post.

    Honestly, if NTVDM was part of Windows then it seems fair to use it, even 3rd party clones.

    • enlyth 1 hour ago
      Yeah I was kind of on the fence with this, but since the last version of Windows that shipped with NTVDM was Windows 10 32bit, and Windows 11 doesn't have a 32bit edition, I decided that using 3rd party tools would be cheating

      I was aiming for something you could double click on vanilla Windows and would just work out of the box

  • Aldipower 3 hours ago
  • t1234s 50 minutes ago
    Does visual studio still package the Spy++ exe that looks like its from the early 90's
  • userbinator 2 hours ago
    Wrote a few small utilities in Win32 in the early 90s; still use them today unmodified, but most recently in WINE. I have some slightly older DOS utilities that are also quite usable.
  • xacky 3 hours ago
    There's probably an old X11 app from the 1980s that could be executed through xwayland somewhere.
    • jpablo 2 hours ago
      I can't even run a binary from one Linux distro to the other, let alone one from a random Unix from the 80s. If a rebuild from source is allowed (which would need to allow modifications to the build system) that's a completely different game.
      • xattt 2 hours ago

            > I can't even run a binary from one Linux distro to the other
        
        Is this actually a thing?
        • jeroenhd 31 minutes ago
          I had to run a Linux binary compiled for Ubuntu 10.something a few years ago. I couldn't get the drivers to work properly in libvirt and getting the binary to run on modern Linux was practically impossible, even with 32 bit support installed.

          The downside of dynamically linked binaries: every tool of medium complexity needs a close-enough version of a common library, and once those get upgraded, the tool dies.

          Most statically compiled version should work with a compatible enough libc, but I haven't seen many old programs like that.

          Wine, on the other hand, runs tools from the 90s just fine, as long as they're 32 bit.

        • 0x0203 2 hours ago
          Many programs are dynamically linked to at the very least, libc. If the system libc is older than what the binary was developed for, it will often fail. Failures going the other direction are less common, but can and do still happen. If the binary was statically linked with everything it needs, you've got a pretty good chance it'll work, but that's a bit harder to do with GUI programs that need to interact with X or Wayland.
        • the__alchemist 2 hours ago
          It depends. I've found for example, if i compile on Ubuntu or Debian, it will probably work on any Ubuntu, Debian, or Debian-based distro released at or newer than the one I compiled it on. There are other cross-compatible examples.

          More broadly, there are things like manylinux and MUSL which allow cross-distro applications.

          • martijnvds 2 hours ago
            Containers fix this.

            As long as the container bundles the right libc, the program should work.

            • the__alchemist 1 hour ago
              I agree - the model I use for why containers (Docker etc) exist is to abstract over Linux ABI incompatibility. I don't think they're a great solution, as it complicates software distribution. I should be able to distribute an executable and have it just work.
      • dekhn 1 hour ago
        I've had static binaries on linux machines that worked across distributions for decades.
    • layer8 2 hours ago
      As an unmodified binary from the 1980s on current Linux/Unix? Highly unlikely.
      • ndiddy 2 hours ago
        From the article, the time to beat is November 16, 1992. This might be possible on one of the BSDs, as FreeBSD and NetBSD both document support for running a.out executables with the 4.3BSD ABI. I guess it would depend on whether anyone had ported X11 to run on a BSD on i386 before then. Alternatively, maybe you'd be able to get something running on SCO OpenServer (if you count that as a current OS, it IS still getting security patches). It documents support for XENIX x.out binaries ( https://www.scosales.com/ta/kb/126704.html ) so you might be able to run software compiled in the late 1980s for XENIX/386.
        • spijdar 1 hour ago
          NetBSD has excellent binary compatible with 80s "unix", the problem is most (all?) of the 80s unix platforms it supports aren't x86.

          Current NetBSD still has good support for running SunOS binaries, though, including graphical ones. I'm certain you could get a SunOS 4.x binary from pre-1992 to run on NetBSD/SPARC. I've no idea how far back you could potentially go on NetBSD/m68k -- probably quite a ways, especially if the binaries are statically linked. SunOS pre-1988 was all static linking!

          (Running "real" 4.3BSD binaries might be hard -- I think NetBSD/VAX defaults to ULTRIX compat, which is an either/or thing versus strict Berkeley Unix compatibility. Same binary format, similar but incompatible syscalls/data structures.)

    • dvh 2 hours ago
      Just used xev today (bought new mouse few days ago and it wasn't responding in chrome so I wanted to be sure).
  • sammy2255 1 hour ago
    If you tried this on Linux desktops you wouldn't get far
  • russellbeattie 24 minutes ago
    I'm imagining a future where Microsoft's Copilot pops up in the corner, Clippy style, and gives you a message like, "Hey, I noticed you're running an app that looks like it was developed when Windows Vista was new. Want me to freshen that up for you?" Then it runs a decomp/recomp process that updates the app at the binary machine code level so that it looks and feels like a modern app without any translation layers or weird bugs. No more user complaints about Windows having an inconsistent GUI.
  • quink 1 hour ago
    That's a year before the first PowerPC Mac even shipped.
  • ModernMech 2 hours ago
    Related: "Chain of Fools : Upgrading through every version of windows (HQ)" (2011), they upgrade Windows 1 through to Windows 7, and demonstrate Doom II and Monkey Island working still at the end. Would be interesting to extend it to Windows 11.

    https://www.youtube.com/watch?v=vPnehDhGa14

    • Dwedit 56 minutes ago
      I can tell that the person making the video never actually tried to run Doom on a real Windows 2000 or XP machine, otherwise they would have noticed that the game has absolutely no sound. Sound support for DOS games in Windows 2000+ was not built into the operating system. You needed to install a third party tool called "VDMSound" if you wanted sound blaster emulation for DOS games.
  • jmclnx 3 hours ago
    Interesting.

    At one tine, Slackware Linux would not recompile binaries unless the program was patched. So there was a time you could find rather old binaries on Slackware, and maybe still on other distros.

    I wonder what the oldest unchanged source/program running on Linux or BSD ? My vote goes to cat(1) :)