As for Macs.... It wouldn't work because of the two major changes in architecture. The original Macs were Motorola 68000 based, then 020, 030, 040. Then they moved to PowerPC 601, 603, 620, G3, G4, G5. Then they transitioned again to x86 Pentium D, Core Solo/Duo's, Core 2 Duo, Xeon's and now Core i3, i5 & i7.
I think you can run from System 1 to 8.6 (or similar) on 680x0. OS 8 was both PPC & 680x0 compatible I think. OS 9 was PPC only if I remember correctly.
You could go from OS X 10.0 to 10.5 on a G3 PPC machine like an iBook or Powerbook. I've personally upgraded an old Powerbook G3 from OS 10.2 to 10.5. Snow Leopard (10.6) is Intel only. Tiger (10.4) was available for both PPC and Intel, as was Leopard (10.5). Lion (10.7) will be 64 bit Intel only, so won't work on pre Core 2 Duo CPUs.
You can still run PPC software using Sheepshaver (or similar, sometimes known as Classic on Intel). Apple included 680x0 emulation in the OS for old apps when they moved over to PPC. Apple also included 'Classic' OS support for OS 9 apps in OS X until the Intel transition.
Personally, on balance I'm quite happy using modern software designed to work on the latest versions that take advantage of new system APIs and features. Software has evolved a lot since MacPaint, etc. and I'm happy to use Photoshop CS5 instead. Would you prefer to use Mosaic or Netscape Navigator than Safari/Firefox/Opera/IE9, etc.?
Still got to say that the video is excellent and informative. My hat is off to the guy who made it.