Since man first used a stick to dig under some roots and accidentally caused a tree to fall on him, humans have been doing stupid things with technology. Since the invention of the microprocessor and instant mass media, this has only become that much easier.

Thankfully 2009 is gone, and with it one of the most tumultuous decades in a long, long time. In that time there’s been some amazing advancements in technology, but those aren’t nearly as fun as some of the catastrophic failures. So here’s a quick round up of some of my favorite technology failures of the past ten years (in no particular order).

The Zune
Now I bought a Diamond Rio 64mb mp3 player back in the day (it was the first widely available portable mp3 player). Eventually I replaced it with a MiniDisk player that I still use when snowboarding, so I have a soft spot for terrible portable music players. But the Zune is a real loser. Incredibly ugly, hard to use, expensive and generally un-cool, the Zune had no chance of taking down the king-of-the-mountain Apple iPod. While some of the newer versions have gained a slight following among the highly valued “children of people who work at Microsoft” crowd, it still hasn’t caught on among the general populace. Newer versions are steadily getting better, but it’s still a really ugly thing to carry around in your pocket. On the plus side, the Zune did make for one of my favorite moments from the Fox sitcom Family Guy:

Beenz.com/Flooz.com
Sure these two terrible tales started off in the late 90’s, but their triumphant explosions weren’t until post Y2K. If you were living in a cave around the turn of the century, these two sites were trying to create an Internet-only currency (think Disney-cash, but they won’t even take it at Epcot). Both sites ran into a whole slew of issues, the least of which being that it’s illegal to create money in most countries if you aren’t the federal government. Once they got over this minor issue, both sites proceeded to gather hundreds of millions of dollars in investment cash, only to blow through it faster than anything I can print here and not get in trouble for. Beenz ranks as one of the biggest busts of the first dot-com era, and one of the worst ideas of the young century.

Webvan
The only other dot-com on my list (although there are so many more that could have made it), Webvan was a great idea if you didn’t take into account that whole “operating costs” thing. The premise is that people can order groceries for a decent price then get them delivered to your house for free. Wondering how they’re supposed to make money? So did the investors; especially after they dumped millions into buying warehouses, vans, servers and 115 Herman Miller Aeron chairs (at $800 a pop). Eventually the basic rules of economics caught up with the company and it imploded, only to be bought by Amazon.com for pennies on the dollar.

Internet Explorer 6
Anyone who works with developers can answer this question: What is the happiest day your office has ever seen? For the rest of you, the answer is the day that your last client stopped requiring IE6 support for their site. Internet Explorer 6 wasn’t just terrible for developers trying to make a site look good though, the software is so insecure that the US Computer Emergency Readiness Team (a part of the Dept of Homeland Security) actually asked Americans to use any other browser. Thankfully it is falling by the wayside, and the newest versions of IE seem significantly less inclined to turn your machine into a thousand-dollar paperweight.

Segway
Remember before this thing hit the market how the mad scientist that is Dean Kamen said it would replace walking? Even the Oracle of Technology himself (Steve Jobs) was quoted as saying this it will be as significant as the personal computer. Turns out that they (along with everyone else who said something like that) were wrong, and this marvel of modern engineering has been successfully regulated to mall cops and bearded professors. Outside of causing a few laughs for the nation (remember when Pres Bush fell off one), and one hilarious day for me in Austin, TX (segway tour + newspaper stand = me gasping to breathe from laughing too hard), the Segway has faded into very funny history.

Twitter Peek
So it’s a $200 handheld that’s about the size of a Blackberry. But unlike a Blackberry it doesn’t do most of the useful things you need a handheld to do, like store contact info, or be a calendar, or make calls. It just — wait for it — checks Twitter. Sure you can write Tweets too, but who seriously thought this was a good idea? I wonder which guy at the table said something to the extent of, “It’s like a smart phone, but you can’t make calls, or write email, or do anything besides Tweet (which you can do from most smart phones using a free app).” I’m not saying that they should be beaten over the head with a sock full of manure, but I’m not saying they shouldn’t be either.

Bluetooth Headsets
Before you get all up in arms about how wonderful Bluetooth technology is, please put down your Perrier and stop freaking out. I’m not saying that the headsets themselves are bad, but like the Trans Am and giant belt-buckles, Bluetooth headsets are used by terrible, terrible people. Unless you’re a trucker (or anyone else who spends all day driving) please take them out of your ear. I promise that when the President calls looking for the nuclear launch codes, I’ll flag you down.