Even now, who can forget (or forgive) Clippy, the animated paperclip? The "office assistant" could serve as the poster child for Microsoft's questionable choices since releasing Windows Version 1.0 on November 20, 1985.
Initially released with Office 97, Clippy was supposed to help users with routine tasks, such as formatting a letter in Microsoft Word. The paperclip was the default character, but others were available, including The Genius (a caricature of Albert Einstein), Power Pup (a dog), and Will (a caricature of William Shakespeare).
Alas, Clippy was despised by users almost immediately for its obtrusiveness. Even so, Microsoft kept pieces of the always-cheerful helper for years. Finally bowing to public opinion, Microsoft made fun of its own creation in a Web campaign in 2001, in the runup to Office XP.
"Office XP works so easily that it's made Office Assistants like me useless. Obsolete. And, I'm told, hideously unattractive," Clippy said on the Microsoft site.
The feature was removed altogether in Office 2007 and Microsoft Office 2008 for Mac.
In fact, Clippy's history predated Windows 95. The concept first debuted in Bob, Windows 95's unsuccessful predecessor.
While not on par with the Windows Vista upgrade fiasco, Clippy reminds us of two elemental truths: First, even a small interface problem can turn happy, content users into a snarky, exasperated mob; second, new features, no matter how innovative or well-intentioned, will alienate users if the tweaks get in the way of getting things done.
Animated paperclips aside, the stakes are much higher for Microsoft these days. In July, the company reported its first-ever quarterly loss. And the company, which has a rocky history selling hardware--remember the Origami?--has now embarked on its first-ever foray into the PC hardware market with its Surface tablet.
In fact, Microsoft has been preparing for the shift away from PCs for at least two years. The question is, can the world's biggest software company make this critical transition smoothly, without a critical misstep?
Can the Windows 8 transition avoid a big blunder? One thing's certain: The Windows 8 critics are already lined up, as InformationWeek's Paul McDougall recently wrote.
Dig into our slideshow for a brief history of memorable Windows goofs and gaffes.