After ten years like these, the remaining 990 in this millennium have gotta be at least a little less goofy, right?

If ever a decade began dumb, it was this one.* When clocks struck midnight on January 1st and the dreaded Y2K bug turned out to be nothing but a mild irritant, it proved once again that the experts often don’t know what the heck they’re talking about.

Which was a relief–and a fitting way to kick off the technological era we’ve lived in ever since. Yes, it’s been an amazing time. But it’s also seen more than its share of misbegotten decisions, bizarre dramas, pointless hype, and lackluster products and technologies–often involving the same people and companies responsible for all the amazing stuff.

So–with a respectful tip of the Technologizer hat to Business 2.0 and Fortune’s 101 Dumbest Moments in Business and, of course, to Esquire’s Dubious Achievement Awards–let’s recap, shall we?

*Yes, we’re aware that the decade didn’t really start until January 1st, 2001, and doesn’t end until December 31st, 2010. Shhhhh.





2000

1. Well, at least I wasn’t killed and eaten by the roving hordes of homeless yuppies. Were you?

Whouda thunk it? It turns out that the world has addressed the Y2K problem remarkably well. Those who predicted widespread starvation, utility failures, medical emergencies, and financial catastrophy probably feel a tad sheepish. And/or disappointed.

2. And it only took them a decade to undo it.

AOL announces that it’s agreed to buy Time Warner on January 10th, a media megamerger that creates an Internet content juggernaut that never quite gels. $260 billion of the combined companies’ $300 billion market cap dwindles away over the next decade before Time Warner rids itself of a vastly less important AOL.





3. Hey, Robinson Crusoe was lonely, too.

On January 19th, top-secret startup Transmeta says it’s shaking up the chip world with its power-efficient Crusoe processor. The CPU’s performance disappoints, Intel cooks up low-power technology of its own, and Transmeta faces delisting from Nasdaq before selling out to a company which then goes out of business.

4. Not the first press release full of fiction, and not the last.

Press-release service Internet Wire is hoaxed by a former employee/community college student who uses it to distribute a fake release saying electronics firm Emulex is restating its earnings. The company loses $2.5 billion of value and the student pockets $250,000 by shorting its stock before being arrested.

5. The “Me” is short for Mediocre. Or maybe Meh.

On September 14th, Microsoft releases Windows Millennium Edition (aka Windows Me). A follow-up to the popular Windows 98 SE and the last gasp of the rickety Windows 9.x platform, the slow and buggy Me goes on to earn the distinction of having the ugliest reputation of any pre-Vista version of Windows.

6. Insert your own Shatner joke here.

An affiliate of name-your-own-price travel site Priceline shutters the dreadful Priceline WebHouse Club. The shopping service let you bid on groceries, and was a swell idea except for the part about prices sometimes being higher than if you’d just strolled into the supermarket, and the no-refunds-even-if-they-don’t-even-have-the-product-you-won policy.

7. Audrey heartburn.

On October 17th, networking kingpin 3Com unveils Audrey, a $500 touchscreen “computing appliance” that does battle with rivals such as the I-Opener and Virgin WebPlayer for a market that–inexplicably–doesn’t exist: People who want to pay about the price of a low-end PC for a machine with a tenth the capabilities.

8. Let’s see Steve Jobs match that throaty yawp.

At an event celebrating Microsoft’s 25th anniversary, Steve Ballmer exhibits his Redmondian passion, earns the nickname Monkey Boy, and inspires an infinite number of YouTube remixes by running around and screaming.

9. Developers, developers, developers, developers, developers, developers, developers, developers, developers, developers, developers, developers, developers, developers.

A few days after “Monkey Boy,” an even more maniacal, preternaturally sweaty Ballmer expresses enthusiasm for developers. Repeatedly. To the point of excess, really.

10. Nice work, Egghead.

Failed computer retailer Egghead, which has reinvented itself as an online merchant, suffers a hacker attack, possibly putting the credit-card information of 3.6 million consumers at risk. Four days pass before it alerts customers, and an investigation into what happened drags on; the company eventually says there’s “no evidence” that any data was stolen, but banks end up spending millions to replace credit cards. The mess doesn’t do anything to help Egghead’s reputation and it files for bankruptcy in August 2001.

2001

11. Because there’s nothing more beloved than hail.

Microsoft announces an array of consumer services code-named HailStorm, including the ability to store personal information on Microsoft servers for use by companies all around the Web. Neither consumers nor companies are thrilled with the prospect, and HailStorm quietly fizzles out in 2002.

12. What a freckin’ lousy idea.

Paraplegic Paul Morgan, also known as “Freck,” announces that he’s going to chop off his feet with a homemade guillotine on Halloween, and Webcast the deed on the Internet before paying customers at CutOffMyFeet.com. He doesn’t.

13. A hell of a grocery bill.

After spending more than a billion dollars on high-tech warehouses, grocery delivery services WebVan declares bankruptcy, lays off two thousand employees, and ceases operations.

14. Pricey mistake, but a pittance compared to WebVan.

In August, once-promising operating system BeOS–the runner-up to Steve Jobs’ NeXT as foundation for Apple’s next-generation OS–is sold to Palm for $11 million. Palm uses BeOS technology in Cobalt, an OS that never actually appears on a shipping device.

15. Tasteless and annoying. Moving and patriotic, but still tasteless and annoying.

In the wake of the 9/11 attacks, Webcam purveyor X10 doesn’t stop its blizzard of pop-up ads featuring pictures of girls in bikinis–it just adds a solemn commemorative message to them.

16. Proof that reincarnation exists. At least for talking paperclips.

In October, Microsoft releases Windows XP, a pretty good operating system tarnished by a mediocre search feature starring a canine “companion.” Yes, he was in XP Pro as well as XP Home. No, Microsoft hadn’t learned a thing from the universal contempt for Office 97’s Assistants. Even a column on Microsoft.com says that some people “loathe” the mutt.

17. I’m still planning to buy one. Once the price hits, say, $74.99.

A mysterious invention known as Ginger is said to be so transformative that cities will be built around it. New Hampshire inventor Dean Kamen’s creation turns out to be a $3000 high-tech scooter; however cool it may be, it can’t possibly live up to the hype, and some cities move to ban it as a hazard to pedestrians.

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