Oldest GUI application that still runs on Windows 11

(blog.enlyth.com)

89 points | by enlyth 2 hours ago

10 comments

  • drnick1 54 minutes 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.
    • dpark 15 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.

    • bcvvvy 16 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.

    • excalibur 32 minutes 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.

      • Borg3 4 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 :)

      • MattPalmer1086 8 minutes ago
        Haha, yes. It does not account for releases which made UX dramatically worse (win 8) which were then reverted to some extent.
  • capnjngl 45 minutes 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 4 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!

  • dofm 58 minutes 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.

  • 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 55 minutes 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 31 minutes 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 45 minutes 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...

  • userbinator 42 minutes 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.
  • Aldipower 1 hour ago
  • lolpanda 42 minutes 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.
    • the__alchemist 27 minutes 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.
      • jen20 16 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.

    • toast0 2 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.

    • jim180 31 minutes ago
      I am having a blast with AI + C + WinAPI. The responsiveness of WinAPI is awesome
  • xacky 1 hour ago
    There's probably an old X11 app from the 1980s that could be executed through xwayland somewhere.
    • layer8 50 minutes ago
      As an unmodified binary from the 1980s on current Linux/Unix? Highly unlikely.
      • ndiddy 18 minutes 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).
    • jpablo 50 minutes 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 42 minutes ago

            > I can't even run a binary from one Linux distro to the other
        
        Is this actually a thing?
        • 0x0203 15 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 24 minutes 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 4 minutes ago
            Containers fix this.

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

    • dvh 44 minutes 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 7 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 57 minutes 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) :)