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Man Puts Computer Through Hell By Installing Every Major Windows Upgrade

Clippy forever

Watch 36 years of Microsoft PC operating systems for consumers flash before your eyes, plus more than a couple dick drawings, in this experiment to challenge the limits of sequential Windows installation.

YouTuber Andrew Tait, or TheRasteri, here updates his 2011 "Chain of Fools" endeavor to include the versions he'd since missed, along with a few new experiments. The original attempt took three days to complete, he wrote on his blog, so it's likely this attempt took even longer.


Beginning with MS DOS 3.10—which he notes wasn't even available as a retail product before version 5, you had to buy a whole computer to get your hands on it—he uses VirtualBox to install every Windows operating system from there on up. This involves copying the disks onto the root of the C drive one by one.

Noteworthy cameos include early publishing tool Pagemaker, ZSoft's PC Paintbrush, the startup "ta-da" from Windows 3.1 that will haunt your memories forever, the Monty Python's Complete Waste of Time game, and again, a penis christening every program that could possibly support the drawing of penises.

It's as difficult to describe this exercise in absurdity as it is to understand why anyone would undertake it. It's best viewed as the nearly 10-minute masterpiece that it is.

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