For a while I’ve been wondering about a silly question, which is, what’s the oldest application with a GUI that will still run on Windows 11 without modifications or emulation.

Given Windows’ excellent backwards compatibility, I expected the answer to be something impressively old.

Sadly, Windows 11 can’t run 16-bit Windows programs by itself, because 64-bit Windows has no NTVDM, so we’re going to have to find something from the early NT era.

I remember asking this question a while ago on an anonymous forum, where someone pointed me to Win32s, and suggested to find an early release version of it with FREECELL.exe.