Oldest GUI application that still runs on Windows 11

(blog.enlyth.com)

47 points | by enlyth 1 hour ago

9 comments

  • drnick1 16 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.
  • capnjngl 7 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/]

  • lolpanda 4 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.
  • userbinator 5 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.
  • dofm 21 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.

  • xacky 25 minutes ago
    There's probably an old X11 app from the 1980s that could be executed through xwayland somewhere.
    • layer8 13 minutes ago
      As an unmodified binary from the 1980s on current Linux/Unix? Highly unlikely.
    • jpablo 12 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 5 minutes ago
        [delayed]
    • dvh 7 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).
  • mijowi 39 minutes 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!
    • bluedino 7 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...

    • elxr 31 minutes 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).
    • weinzierl 18 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.

  • Aldipower 36 minutes ago
  • jmclnx 19 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) :)