I'm geeking out, and I love reading about the development, design decisions and choices in OS development, particularly retro ones (Windows 9x and prior, the Mac OS, etc) The shortfalls, the evolution of the GUI.. a lot. I found some stuff on an early build of the Win95 taskbar, that was interesting..
Quick couple of examples.
http://arstechnica.com/articles/paedia/gui.ars/2
http://toastytech.com/guis/indexwindows.html
http://www.guidebookgallery.org/screenshots/win31
And theres a website somewhere with tales of the Mac creation etc.
Any suggestions for good reads?


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