YHK - yet another hacker news clone

Oldest GUI application that still runs on Windows 11

109 points enlyth 2 hours ago 40 comments

mijowi 1 hour ago | parent

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!

elxr 1 hour ago | parent

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 45 minutes ago | parent

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!

weinzierl 1 hour ago | parent

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.

bluedino 59 minutes ago | parent

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...

xacky 1 hour ago | parent

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

layer8 1 hour ago | parent

As an unmodified binary from the 1980s on current Linux/Unix? Highly unlikely.

ndiddy 32 minutes ago | parent

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.

jpablo 1 hour ago | parent

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 56 minutes ago | parent

    > I can't even run a binary from one Linux distro to the other
Is this actually a thing?

the__alchemist 38 minutes ago | parent

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 18 minutes ago | parent

Containers fix this.

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

0x0203 29 minutes ago | parent

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.

dvh 58 minutes ago | parent

Just used xev today (bought new mouse few days ago and it wasn't responding in chrome so I wanted to be sure).

dofm 1 hour ago | parent

> 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 1 hour ago | parent

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) :)

toast0 10 minutes ago | parent

FreeBSD /bin/cat has lots of recent changes of substance: https://github.com/freebsd/freebsd-src/commits/main/bin/cat/...

Otoh, /usr/bin/true has only minor changes since initial import (1994) https://github.com/freebsd/freebsd-src/commits/main/usr.bin/...

/usr/bin/false is similar

drnick1 1 hour ago | parent

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.

excalibur 46 minutes ago | parent

> 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.

MattPalmer1086 22 minutes ago | parent

Haha, yes. It does not account for releases which made UX dramatically worse (win 8) which were then reverted to some extent.

Borg3 18 minutes ago | parent

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 :)

thesdev 11 minutes ago | parent

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?

PorciiVorbesc 10 minutes ago | parent

>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 take. I started my computing journey with Windows 95, meaning I have some emotional attachment to it and I'm as millenial with knee pain as they get not Gen-Z, and can't imagine using W95 today productively in a non-ironic way. Windows 95 was perfect ... for what people did on computers in 1995, not for what I do now in 2026 on the HW of today. May it rest in peace, but I'll take my modern OS.

john01dav 13 minutes ago | parent

> 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".

bcvvvy 30 minutes ago | parent

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.

dpark 29 minutes ago | parent

> 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.

capnjngl 59 minutes ago | parent

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 18 minutes ago | parent

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!

userbinator 56 minutes ago | parent

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 56 minutes ago | parent

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.

jim180 45 minutes ago | parent

I am having a blast with AI + C + WinAPI. The responsiveness of WinAPI is awesome

the__alchemist 41 minutes ago | parent

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 30 minutes ago | parent

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.

floydnoel 3 minutes ago | parent

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.

toast0 16 minutes ago | parent

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.

chuckadams 13 minutes ago | parent

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.

ModernMech 21 minutes ago | parent

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 7 minutes ago | parent

> 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.