25 years ago is 1995, and around the release of Windows 95, the first 32-bit version of Windows.

A .exe compiled 25 years ago would probably be a 16-bit executable, and Windows stopped supporting Win16 code in Windows 7. WINE theoretically supports it, but 16-bit userspace code and a 64-bit kernel do not mix well.

> the first 32-bit version of Windows.

Windows NT was released in July, 1993. Almost exactly two years before Windows 95.

In 1997 I joined a company where I was doing Win32 coding, on a Windows NT code base that dated back to 1995. The code base also had parts targeting Windows CE client devices. (The company was an extremely early adopter of that platform; they might have done some of the development before CE was officially released in 1996. Anyway, that's another 32 bit Windows from almost 25 years ago, and less of a hack than 95.)

I don't think that's true. The 32-bit versions of Windows still run 16-bit binaries.

Just run a 20 year old binary and worked fine; I'ld lie if I said it didn't impressed me