Upgrading from System 4.1 to macOS 10.14 Mojave, by upgrading through every version. A long chain, sped up.

Software used:
Mini vMac: System 4 - 7.5.5
Basilisk II: Mac OS 8 - 8.1
SheepShaver: Mac OS 8.5 - 9.0.4
Qemu: Mac OS 9.1 - X 10.4
Parallels Desktop 13: Mac OS X 10.5 - 10.14 (EFI Patch to run non-server 10.5 and 10.6)

ScreenFlow 7 - Recording
All versions of Mac OS from 4.1 to 10.14 (Floppy Disk/CD/DVD Images / Mac App Store)
macOS 10.13.6 High Sierra as the Host OS

I started at System 4.1 because the machine I was emulating in Mini vMac would only run that low at the time of recording. The file system used before System 4 is different (MFS as opposed to HFS), but this shouldn't be a problem.

The intro videos for the versions of Mac OS X that have them are also shown.

Timestamps:

00:00 - System 4 & 5
01:00 - System 6
01:52 - System 7
04:23 - Mac OS 8
06:45 - Mac OS 9
11:09 - Mac OS X v10.0 (Cheetah)
15:10 - Mac OS X v10.1 (Puma)
18:22 - Mac OS X Jaguar (v10.2)
21:12 - Mac OS X Panther (v10.3)
23:32 - Mac OS X Tiger (v10.4)
26:32 - Mac OS X Leopard (v10.5)
28:02 - Mac OS X Snow Leopard (v10.6)
30:17 - OS X Lion (v10.7)
31:50 - OS X Mountain Lion (v10.8)
33:43 - OS X Mavericks (v10.9)
35:29 - OS X Yosemite (v10.10)
36:53 - OS X El Capitan (v10.11)
38:14 - macOS Sierra (v10.12)
39:38 - macOS High Sierra (v10.13)
41:20 - macOS Mojave (v10.14 Beta)

5 Year Update:    • Upgrading Every Version of macOS