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So far, to my recollection but remember that MS has 25+ years under its bloated belt...
* MS released a webdings font; where certain letters placed next to each other made a nasty iconic representation of an airplane, WTC building, Star of David, and skull'n'crossbones. Uh-oh.
* MS Word's clip art search tool, when typing in the word "monkey", not only returns monkey bar gyms and monkeys, it also returned images of African Americans. Whoops.
* Another MS font, introduced in Office 2003, featured swaztikas. A "patch" fixes this bug. (the "patch" being a replacement font, whoodpie-doo.)
* When Microsoft released Windows 2000, they told everybody (even with pictures in some cases) that Windows 95 was buggy and crash-prone. (anybody else dissing their own predecessor would go out of business and/or get sued!)
* When Microsoft released Windows XP, they told us all it was how Windows 2000 was supposed to be. (so why did they then charge astronomical sums of money for it?)
* Windows Longhorn - now renamed Vista for some bizarre reason - has had so many lofty ambitions whittled away (chiefly a new type of file systems that Unix has had for many years already, but there were others) that "Vista" seems to be just another lie; many of whose new 'features' (a new GUI and little more) won't work unless you have a top-of-the-line system; otherwise it'll look just like Windows 2000's user interface (likely XP's cruddy Luna tinkertoy interface).
* Bill Gates is on record stating that nobody would ever need more than 640Kb. Whoops.
What else? I'm sure there are many!
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