Oldest GUI application that still runs on Windows 11

mijowi

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!

Aldipower

https://solitairealonetogether.com/

xacky

There's probably an old X11 app from the 1980s that could be executed through xwayland somewhere.

dofm

> 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.

jmclnx

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) :)

drnick1

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

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/ ]

userbinator

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.

lolpanda

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.

ModernMech

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

MisterTea

> 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.

quink

That's a year before the first PowerPC Mac even shipped.

tgtweak

I'm reminded of this amusing and brilliant post: https://blog.hiler.eu/win32-the-only-stable-abi/

sammy2255

If you tried this on Linux desktops you wouldn't get far

kidel001

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.

mattbee

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.

andai

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

xnx

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.

t1234s

Does visual studio still package the Spy++ exe that looks like its from the early 90's

russellbeattie

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.