HackerTube / Video
Chain of Fools : Upgrading through every version of windows (HQ)
TheRasteri

TheRasteri installs MS-DOS and Windows 1.0, then upgrades in place through nearly every Windows version up to Windows 7, checking which programs survive. Even Doom from 1993 still runs at the end.
HN cites it as evidence of Microsoft's backward compatibility and of upgrade engineering done well.
12 Hacker News mentions · 2011–2021