The first version of Windows hit the market in November 1985. I suspect many of our readers hadn't even been born back then, but it was an era in which Windows barely worked as a graphical environment slathered on top of MS-DOS. With more than three decades on its shoulders, Windows evolved into a complete operating system in its own right, and never lost the ability to upgrade, detecting elements from an earlier version to incorporate into the next. That said, how does a video showing the complete upgrade route in Windows, from version 1 to version 10, sound?

My main computer has a full Windows reinstall pending, and I'm basically waiting for Microsoft to release the Creators Update of Windows 10 so that all its hotfixes end up integrated into a single official ISO image. If the final result doesn't appeal to me, I guess I'd have no trouble going back to Windows 7, aside from the Windows Update sessions that take three or four hours (on a good day). However, what brings us here today is not a downgrade, but an upgrade. Better yet, it's the great-great-grandfather of all upgrades. In March 2011, the TheRasteri channel published a video called 'Chain of Fools' on YouTube, in which it shows the entire upgrade process from Windows 1.0 to the latest edition available. Six years later we have three new versions of Windows, and the decision was to update the content.

Upgrading Windows from Version 1 to Version 10
Windows

Upgrading from Windows 1.0 to Windows 10

(Note from the editor: I must warn that there's a bit of NSFW content. The narrator likes to draw certain things in Paint…)

The video begins with the installation of IBM PC DOS 3.10, which was one of the most common versions when Windows 1.0 hit the market. It also highlights the availability of some Windows 1.0 functions in standalone tools, such as Aldus PageMaker. Windows 2.0 managed to retain the interface configuration with several manual settings, while Windows 3.0 imported everything automatically, also detecting previous applications.

Installing Windows 3.1 required an upgrade to MS-DOS 5.0, and as a reference, an old Monty Python game was installed. Windows 95 kept the color scheme, and Windows 98 made a couple of mistakes (two versions of Internet Explorer, 4.0 for W98 and 5.0 for 3.1). Unlike the original video, this time he decided to upgrade Windows 98 to Windows ME, without major incidents.

Windows XP demanded converting the partition to FAT32, and it was the first to discard the color configuration because of its factory theme, but all the programs installed since Windows 3.0 kept working, even those that didn't work on Windows 9x. The upgrades to Windows Vista (with an NTFS conversion in between) and Windows 7 maintained similar backward compatibility. As expected, Windows 8 turned the interface upside down, although the old programs were still there, and most of them worked fine.

After going through Windows 8.1, the video ends with Windows 10, which once again ignored any interface customization. However, when tracing old Windows 2.0 programs on the hard drive, TheRasteri verified that they still ran without problems, as did the Monty Python game. In short: it's a nightmare like few others, but at the same time it confirms that Windows backward compatibility withstands almost everything.