Technology’s spawned plenty of headlines throughout 2008 — and cowering next to every story of success is a slip-up someone would like to forget.

We’ve compiled a dozen of the year’s worst tech-related embarrassments. While the good stuff will eventually all blend together, these bad moments will live forever in infamy. Brace yourself for some blush-building blunders.

1. Most Embarrassing Service Lifespan

Goes to: Lively by Google

tech-embarrassments-livelyIn July, Google excitedly introduced its answer to virtual world Second Life: a family-friendly cyber-environment called Lively. That’s right, red light regulars — no sex, no dirty talk, no virtual action in this joint. “[People] know we’re not going to be putting porn in there, and they’re looking at it and thinking it’s a safe place to enter,” a Google exec explained at the time of Lively’s launch.

Fast-forward one month, and Lively had turned into a virtual groping ground for preteens worldwide. Still, these middle schoolers had to get creative, “thrusting” robot tentacles to “pleasure” other avatars.

Mashable put it best: Google had built a service with “all the fun of a virtual chat room [but] none of the ‘benefits’ offered by its competitors.” And the public seemed to agree — in mid-November, Lively got the ax, just four months after its debut.

2. Most Embarrassing Online Exposure

Goes to: Chris Cooley’s Phallic Fumble

tech-embarrassments-chris-cooleyComing in with what can only be described as one of the “smaller” mistakes of the year is Washington Redskins’ tight end Chris Cooley. Cooley, who maintains an online blog of his NFL endeavors, posted a shot of himself studying the team playbook before a game. Studying the playbook naked, that is.

Now, to be fair, you don’t see much in the shot. In fact, that might be an understatement. The photo — removed from Cooley’s blog but available here, if you must see it — shows the book on Cooley’s lap with a little something extra hanging out below. And the object is not, shall we say, hard to recognize.

An apology was posted a day later: “We are very sorry that we showed a penis on our website all day yesterday. That was by no means our intention and we did not want to offend anyone.”

Anyone can make a fumble, but you’ve gotta wonder how this one slipped by. Looks like someone wasn’t using his head. Er… yeah, nevermind.

3. Most Embarrassing E-Mail Revelation

Goes to: The Sarah Palin-Yahoo Mail Saga

tech-embarrassments-sarah-palin-yahoo-mailIn case our next winner didn’t have enough public humiliation this year, the Internet brought her one more dose. We’re talking, of course, about Sarah Palin and the now-infamous Yahoo Mail hack.

Palin, it had been discovered, was using a couple of Yahoo accounts for official government business — a move questioned by activists who claimed her Alaskan administration was trying to avoid laws requiring government e-mails to be placed in public record. Seemingly, it also didn’t sit well with a hacker.

The guy used Yahoo Mail’s simplistic security protection to pose as Palin and reset her password, then proceeded to post images from her account onto the Web. Whoopsie daisy.

This, my friends, is why we don’t use low-security Webmail services for official government messaging.

4. Most Embarrassing Display of Desperation

Goes to: Microsoft Live’s Cashback Promotion

tech-embarrassments-live-cashbackUnable to secure any traction for its Live search engine, Microsoft’s tactic of 2008 has been bribery — and lots of it. The company first started its Cashback program in May, basically offering users money to turn to Live for search. You look up products on the struggling site, and you get money back on any resulting purchases you make.

The initial idea was groan-inducing enough. But then, despite statistics showing Microsoft had actually lost market share since starting the program — a full 6.5 percent drop from April to October — the Live crew kept insisting the program was a success, even expanding it in early December.

(Google, by the way, gained market share in the same time Microsoft’s Cashback program was “working.” Even Yahoo somehow managed to grow.)

Search for “desperate,” and this sad stunt should show up high.

5. Most Embarrassing Result of Internet Reporting

Goes to: The Death (and Subsequent Near Death) of Steve Jobs

tech-embarrassments-steve-jobs-obitWhat a year for Steve Jobs. Apple’s man main briefly died, then a couple months later had a heart attack and was rushed to the hospital — all while he unwittingly went about his day-to-day life.

The first fake scare for the Mac master came in August, when Bloomberg mistakenly published Jobs’ obituary to its Web site. The news service had prewritten a 17-page account, and someone hit the wrong key.

Jobs was quickly resurrected, but it didn’t take long for his second bout of mistaken misfortune to arrive. In October, a story posted on CNN’s citizen journalism site, iReport, quoted a “reliable insider” as saying claimed Jobs had suffered a “major heart attack” and was hospitalized. This time, Apple’s stock shot down as the news quickly spread over the Internet. Needless to say, the whole thing turned out to be a hoax.

“Unfiltered” news, indeed.

6. Most Embarrassing Data Investigation

Goes to: The TSA’s Lost Laptop Probe

tech-embarrassments-tsa-laptopLeave it to America’s Transportation Security Administration to lose a laptop full of sensitive data, start a full-fledged investigation — then realize the thing was sitting inside its office the whole time.

Did you hear about this one? The TSA reported a checkpoint laptop at San Francisco’s airport as missing in August. The computer had tens of thousands of passengers’ personal information on it, and it couldn’t be found anywhere.

The TSA shut down its prescreening program and started a search. National media outlets were notified, and reports hit papers across the country. Then, the TSA realized the laptop had been in its own office all along. Oops.

Actually losing the thing might have been less embarrassing in the end.

7. Most Embarrassingly Overhyped Launch

Goes to: Cuil

tech-embarrassments-cuilFew Internet startups have seen the kind of hype that Cuil managed to build leading up to its launch. The search engine, started by some former Googlers, promised to be “bigger, faster, and better” than the giant G. It was built on “contextual” search that would change the way the Web worked, we heard. Tech blogs went ga-ga with coverage anticipating the mysterious new entity.

Then the site actually went up, and the expectations went right down. Laughable results and overwhelmed servers combined to kill the Cuil buzz faster than you can say “Sergey Brin.” These days, Alexa data shows the search engine seeing less than a single percent of Internet users visiting its site, compared to Google’s roughly 28 percent.

Bigger than Google? A bigger failure, perhaps. Guess Cuil isn’t so cool after all.

8. Most Embarrassing Public Stance

Goes to: The Associated Press Take On Bloggers

tech-embarrassments-ap-bloggersThe way we get information is constantly evolving. Alternative media sources are taking an increasingly prominent role in the delivery of news, and bloggers are a big part of that mix. You might think, then, that one of the world’s leading news organizations would learn how to adapt and embrace the changing culture for its own benefit. Of course, you’d be wrong.

Instead, the Associated Press decided to fight the blogosphere this year, formulating its own set of standards as to how online publications could use its information. Fair use doctrines be damned, the AP said using even small excerpts of its stories within a blog was out of line and out of the question.

The AP did accomplish something with its silly stance: It alienated itself from some of the most influential players in modern media. Countless blogs and online publications pledged to stop referencing and linking to Associated Press stories altogether. Incoming links are often called the “currency of blogs,” playing a significant role in visibility and search placement. Not that a company that just slashed 10 percent of its workforce needs to worry about such things. Riiiight.

Well-played, AP. Well-played.

9. Most Embarrassing Mobile Moment

Goes to: iPhone 3G Activation

tech-embarrassments-iphone-activationEveryone knew the first day of iPhone 3G sales was going to be huge. Everyone, it seemed, except for Apple.

The company suffered what can only be described as a major meltdown, as subscribers who’d waited in long lines found themselves unable to activate their new phones. In-store customers were turned away and asked to try activating their phones later from home. But activation servers wouldn’t work over the Internet either, leaving people with a useless device and no functioning phone.

Gee, if only Apple could somehow have anticipated the response — or maybe had some past experience with overwhelmed servers to learn how to handle it — maybe things could have gone more smoothly.

10. Most Embarrassing Response to a Security Flaw

Goes to: The Boston Transportation Hack Fiasco

tech-embarrassments-subway-hackFile this one under “How Not to Handle a Security Flaw”: A couple of students from MIT found a loophole within Boston’s “T” subway system. The flaw, they discovered, would let anyone add limitless value onto the system’s payment cards. The students, planning to present their findings at the DEFCON 16 annual hackers’ conference, met with transportation officials in advance to discuss their report.

Then, just before the conference, the Transportation Authority filed a federal complaint and got a temporary restraining order to keep the students from talking. In doing so, it also inadvertently published the students’ full report (PDF) to the Web as part of public record.

It gets better, though. Even after realizing anyone in the world could access the entire report, the Transportation Authority fought to extend its restraining order against the students. Long story short, it got shut out. A federal judge denied the request, the students got an “A” on their project, and the security flaw got far more attention than it would have had the Transportation Authority not thrown its fit.

Irony can be so satisfying sometimes.

11. Most Embarrassingly Transparent Lie

Goes to: Metallica’s “We’re Okay With Filesharing”

tech-embarrassments-metallica-filesharingMetallica seemed to be singing a new tune in 2008. Eight years after drummer Lars Ulrich led the war against filesharing, ultimately resulting in the shutdown of the original Napster, the band worked hard to give the appearance of a reformed approach.

Ulrich released a video in which he talked casually about sharing Metallica’s music online. “The band is trying to salvage its reputation by embracing, at long last, the realities of online music,” Wired.com observed at the time.

The little fella even went as far as to act totally cool with the fact that his band’s then-unreleased CD had been leaked onto the Web. “It’s 2008 and it’s part of how it is these days, so it’s fine. We’re happy,” he insisted.

So happy, in fact, that the band quietly cancelled an interview with a newspaper after learning the reporter had listened to some of those leaked tracks online. In a similarly sneering display, Metallica demanded numerous bloggers take down advance reviews they’d written of the new album. Their reviews were based on a listening party held by the label itself. It’s sad but true.

Could these guys be any more out of touch with the digital age? Maybe they should consider a partnership with our pals at the AP — we hear they’re big into outdated ideology, too.

12. Overall Achievement In International Embarrassment

Goes to: Jerry Yang

tech-embarrassments-jerry-yangWho else could top our list of biggest tech embarrassments but Mr. Yahoo himself? For his endless string of amazingly asinine actions, we hereby award Jerry Yang the Overall Achievement in International Embarrassment. The race wasn’t even close.

There’s not much that can be said about Yang’s year that hasn’t already been discussed ad nauseum. The guy drove his company into the ground, making dumb decision after dumb decision — all while continually talking up how great things were going and how Yahoo’s big day was right around the corner. Even in announcing his long-overdue resignation in November, Yang disregarded what everyone in the world could see and kept pretending he’d done a great job:

“It’s been an extraordinary year here at Yahoo.”

“I truly believe we’ve made tangible progress in bringing our strategic vision to life.”

“Now I believe the time is right for us to bring in a new leader — someone who will build on the important pillars we’ve put in place and who will take the reins on the critical decisions our company faces.”

Important pillars? Like the share value that’s now a third of what Microsoft offered to pay when you turned them down? Critical decisions? Like how to undo the immeasurable damage you’ve done?

Oh, Jerry… Jerry, Jerry, Jerry. All I can say is that “Chief Yahoo” is perhaps the most fitting title I’ve ever seen a man hold. Congratulations.

* * * * *

So that does it — our Top 12 Tech Embarrassments in 2008. Some of the memories make us laugh; others still cause us to cringe (cough cough Yahoo). And there are, no doubt, countless other mess-ups we didn’t even get to. Feel free to make your own additions in the comments section below.

Of course, the year isn’t quite over yet. Here’s hoping no one Yangs up another tech company in 08’s remaining days, or we’ll have to go right back to square one. Now, that’d just be plain embarrassing.

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