Watch a Guy Install Every Version of Windows and Draw Dicks in All of Them

Image: YouTube / Gizmodo

Just for fun, a random YouTuber upgraded a single computer from Windows 1.0 to Windows 10—including every version in between. Seeing the whole process unfold before your eyes is nostalgic as hell. Watching a guy draw dicks in every version of Windows is a little weird, though.


Not only does this installation enthusiast draw dicks in every version of Windows, he also mixes up his methods. Obviously, there’s the obligatory early MS Paint dick drawing. But later in the version history, you’ll see dicks in PageMaker as well as Word and Excel.

Image: YouTube / TheRasteri
Image: YouTube / TheRasteri

It’s like the Windows-based version of Jonah Hill’s strange dick-drawing habit in the movie Superbad.

All dick drawings aside, you’ll get a thrill out of seeing how hilariously awful the first version of Windows was. And it’s a blast to see games like SkiFree and PipeDream again. Remember Windows ME? I don’t.


Senior editor at Gizmodo.

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I remember Windows ME. I had a Gateway computer (remember those?) which came with it and at one point decided to reset itself, erasing everything on it.

Which now reminds me that there used to actually be Gateway stores. Like seriously. Like the Apple store, but Gateway products. That seems so weird to think about these days.