Oldest GUI application that still runs on Windows 11

(blog.enlyth.com)

137 points | by enlyth 2 hours ago

13 comments

  • drnick1 1 hour 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.
    • dragontamer 0 minutes ago
      [delayed]
    • cowlevel 28 minutes 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.
      • frantathefranta 15 minutes 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 59 minutes 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 11 minutes ago
        It's been that way forever, did you forget about the Borland buttons? Colorful icons on them, much bigger, different shading.
    • okanat 28 minutes 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.
      • theandrewbailey 16 minutes 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.
      • abhgh 17 minutes ago
        I loved Windows Aero and the flip 3D view - the latter mostly because it looked so cool for that time!
    • Grosvenor 11 minutes 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.

    • fellowniusmonk 25 minutes 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.

    • dpark 57 minutes 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 29 minutes 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.

    • excalibur 1 hour 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 42 minutes 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 50 minutes ago
        Haha, yes. It does not account for releases which made UX dramatically worse (win 8) which were then reverted to some extent.
      • nubinetwork 13 minutes ago
        Not until they settle on one control panel.
      • Borg3 46 minutes 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 39 minutes 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.

          Super daft and somewhat insulting take. 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 not Gen-Z, and 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 21 minutes 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 12 minutes 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. "Classic windows" makes sense if you also use it in a classic way, meaning launching and using one full screen app opened at a time, maybe two and that's it, with the desktop being the center piece from which you launch apps, instead of the browser, like it is today.

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

              Cygwin is CLI, not UI, which is what I was 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. You can't customize it anymore in the W95 way, such as having a Matrix or Rollercoaster Tycoon theme on it, but I don't need that anymore since I'm old and don't have time for that anymore.

              >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. Please explain yourself here what you mean since you seem to be contradicting yourself. Or do you just mean corporate windows and not home windows?

        • thesdev 39 minutes 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 23 minutes 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 12 minutes 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 23 minutes 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.
  • tgtweak 9 minutes ago
    I'm reminded of this amusing and brilliant post: https://blog.hiler.eu/win32-the-only-stable-abi/
  • dofm 1 hour 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.

  • capnjngl 1 hour 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 46 minutes 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!

  • mijowi 1 hour 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 1 hour 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 1 hour 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 1 hour 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 1 hour 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...

  • lolpanda 1 hour 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.
    • adzm 8 minutes 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.
    • okanat 23 minutes 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.
    • the__alchemist 1 hour 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.
      • Doohickey-d 9 minutes 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.

      • floydnoel 31 minutes 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.
      • jen20 59 minutes 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.

    • chuckadams 41 minutes 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.
    • jim180 1 hour ago
      I am having a blast with AI + C + WinAPI. The responsiveness of WinAPI is awesome
    • toast0 45 minutes 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.

  • MisterTea 35 minutes 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 10 minutes 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 1 hour ago
  • userbinator 1 hour 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.
  • quink 21 minutes ago
    That's a year before the first PowerPC Mac even shipped.
  • xacky 1 hour ago
    There's probably an old X11 app from the 1980s that could be executed through xwayland somewhere.
    • jpablo 1 hour 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.
      • dekhn 14 minutes ago
        I've had static binaries on linux machines that worked across distributions for decades.
      • xattt 1 hour ago

            > I can't even run a binary from one Linux distro to the other
        
        Is this actually a thing?
        • 0x0203 58 minutes 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 1 hour 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 47 minutes ago
            Containers fix this.

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

    • layer8 1 hour ago
      As an unmodified binary from the 1980s on current Linux/Unix? Highly unlikely.
      • ndiddy 1 hour 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 22 minutes 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 1 hour ago
      Just used xev today (bought new mouse few days ago and it wasn't responding in chrome so I wanted to be sure).
  • ModernMech 50 minutes 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

  • jmclnx 1 hour 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) :)