Watch a man install every major Windows upgrade from the past 30 years

Introducing Endless Mode: A New Games & Anime Site from Paste
In 2011, Andrew Tait of the YouTube channel TheRasteri decided to test the upgrade capabilities of Microsoft Windows by installing every major version of the operating system on a virtual machine. And now he’s back with another video that does all that plus the three additional Windows updates that have been released since 2011. But rather than just tack those updates onto the end of his previous project, he starts all the way back at the beginning to address some shortcomings in the original experiment. And along the way he squeezes in as many dick drawings as possible.