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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.
Before Windows 95, there was Bob.
Code-named "Utopia," the non-technical graphical user interface was released at the end of March, 1995. The child-like GUI, built around a virtual room and a virtual house, used common objects as metaphors for computer applications like word processors and spreadsheets. Happily, Bob's dollhouse fell into foreclosure, and XP's comparatively grown-up GUI arrived on tens of millions of desktops.
During the dark days of the U.S. Department of Justice's antitrust investigation against Microsoft in 2000, tone-deaf forces within Microsoft's corporate marketing organization apparently thought it would be helpful to put the company's founder and chairman, Bill Gates, on the airwaves to speak directly to the American people.
The resulting "fireside chat" TV commercial, featuring Gates wearing a blue sweater and seated at a table while an acoustic guitar played, was meant to soften the prevailing image of Microsoft as a monopolistic bully. In what some would call a cringe-worthy statement, Gates says at one point: "We've been writing great software for the past 25 years."
Anyhow, few people remember the ad. Much more memorable was the Internet meme a few years later that envisioned Gates as a Borg, declaring, "Resistance is futile."
Even after Microsoft's premature attempt to enter the tablet market with Windows XP Tablet PC Edition in 2002, there was Origami--which became the Ultra-Mobile PC when it was released.
The offering prompted an InformationWeek editor at the time to declare it "the hands-down winner for Most Disappointing Product Of 2006."
In January, 2007 millions of us rushed to upgrade our PCs to Vista, eager to try the widely hyped successor to Windows XP. But a slew of upgrade issues, including missing drivers and annoying user account controls, soured many people on the process. Worse for Microsoft, businesses largely sat out the Vista upgrade, rightly worried (this time) about compatibility issues.
The early 2011 broad strategic partnership between Finnish handset maker Nokia and Microsoft arrived with much fanfare. Research outfit Gartner went so far as to predict the co-developed phones would outsell Apple's iPhone by 2015. Fast-forward to today, as financially struggling Nokia tries to push its latest Windows Phone, the Lumia 501, as a low-priced option in emerging markets.
Ever wonder why you can't directly cut and paste from Word into a plain-text or HTML document? It's because Microsoft's HTML rendering isn't vanilla. Web types get especially hot about Microsoft's choice of using the Word HTML rendering engine in Outlook 2007 and up. "It has set email marketing back 10 years," griped one.
Acquired by Microsoft in late 1997, Hotmail is still the largest Webmail service worldwide--but of late it has been losing marketshare, while Google's Gmail has enjoyed percentage growth in the double digits. Hotmail went through countless UI changes over the years, but it never quite seemed to be a priority for Microsoft. In the summer of 2012, Microsoft replaced it with a new free email account, Outlook.com, promising a cleaner look that's better suited to tablets and smartphones. Can Outlook.com wrest email users away from Gmail? That's the plan.
Some critics have already declared Microsoft's Surface tablet a goof, for the simple reason that the product line is bifurcated and, they say, bound to confuse customers. Surface RT, the model powered by the Windows 8 variant known as Windows RT, relies on the new Metro interface of Microsoft's Windows 8 but is incompatible with many apps that will run under Windows 8. But there's also Surface Pro, which runs Windows 8 Professional and can run desktop software.