Top 12 Tech Embarrassments in 2008
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
In 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
Coming 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
In 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
Unable 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
What 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
Leave 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
Few 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
The 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
Everyone 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
File 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”
Metallica 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
Who 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.











This was a great read and a good list of items. Metallica lost me as a fan years ago with the napster deal. They shot their fans in the face with that crap.
I wiped it off and walked away from them for good. I think their early stuff is best. The last few albums absolutely suck.
Good post…and good rating by you my friend
Good list; I do remember most of them, but the one that really stands out is Lars Ulrich from Metallica… yeah, like you said, after they spear headed the movement to trash napster, they turn around and pose like that wasn’t their intent… gah, everytime I think back to the whole ordeal it makes me sick.
Fantastic list, very funny. For me, the subway saga made me laugh most!
#3, he was not a hacker
Definitely a good read
Cheers !
#2 was epic. Don’t blog naked.
Interesting read, I don’t think its ever possible for Metallica to fix their reputation.
That was a great read indeed.
Dint knew about #8. Thanks for telling me,will boycott AP from now on
Because Metallica chooses to be paid for what they provide doesnt make them an embarrassment. I wonder how all those people who “stole” from them on Napster would like to work for free. I know I wouldn’t.
I would have include the Spore-Amazon fiasco in this list, too. That’s embarrassing!
Your information on Metallica is seriously incorrect. Their record label asked the blogs to remove the reviews, but when the band themselves found out, they told the blogs to put them back up, and issued a statement on their website saying that they had no part of that, it was just a screw up by their record label, and there was no reason they would want reviews taken down (especially since they were mostly saying how great the new album was) In addition to that, they offered free downloads and streams of about half the album and a music video to members of the warner brothers ‘Mission Metallica’ Website. If you are going to pretend you are in a high enough position to judge people, as if your words are held with such high regard, at least be responsible enough to have all the facts. Besides, it might be hard to beleive for someone who’s NOT a billionaire, but Napster wasn’t about money. They got pissed off because a song they were working on got pirated and a copy of the unfinished song made it to the radio via napster. It was about control of their work.
i know a guy who has been using the subway hack for years.
Metallica. I won’t download even half of a byte of their crap. I won’t listen to it. I certainly won’t listen to it. And I’m very vocal about what I think specially of Lars.
Been that way for years, will continue to be that way for many more.
I still remember a bunch of interviews from that tool.
Yes Vanessa, yes. Indeed. But this is how it works:
First you see a Lars talking about how he used to copy (on tape) everything he could when he had a few years less and how it was awesome and all that.
Then you see Lars on the high horse teaming with the retards who sue you for a quintillon dollars when you have copied two songs worth almost zilch.
Oh, as it happens it’s legal to download music in my country. You can guess which I’m not? I’m sure they’ll be happy.
In the stakes of embarrassing data loss, I’m ashamed to say, the UK gov’t beats the TSA hands down for this year!
Vanessa – regarding Metallica, I don’t think it’s so much that they, and other musicians, shouldn’t be paid for their work. It’s more to do with attitude towards it now, and how they contradict themselves.
yeah I have to agree with most of these. Some I had no clue about but while reading…Critical fails, especially Yahoo. I wonder if they may go back and fix some of the idiotic mistakes that have been made with their products before the last of their user base vanishes. As a long time user of yahoo mail and messenger I’ve seen a steadily growing decrease in standards. In the effort to “clean up” their chat rooms they’ve made them impossible to use (except of course for the bots they were trying to get rid of in the first place)
and since the Metallica bit seems to be head of the comments list… Its not their stance against it that makes them fail (although given the price of music these days I am all for file sharing) Its the fact that they turned face so quickly. No one will believe them now. I also have to agree, their more recent music just isn’t as good as the older stuff.
I would definitely add the Stumbleupon-eBay fiasco to that. eBay should have known that they would not be able to use Stumbleupon to make serious money, it was destined to fail, it was a bad idea!
Note: I hope that Google buys Stumbleupon some day, that would be so great, because they could actually do something with it and be successful.
@Vanessa
if you don’t want to make shit money, (or work for ‘free’) rock star was probably a poor career choice.
@wow
you are a loser. lars is worse than kanye… and he looks like hes been doing coke for like 15 years straight, too. (was he always this ugly?)
I’m tired of people overhyping the Microsoft-Yahoo! deal. It was just an unsolicited takeover offer that ended without an agreement, when the larger company refused to negotiate.
Your comment, “Like the share value that’s now a third of what Microsoft offered to pay when you turned them down?” also fails to recognize that MICROSOFT’S stock price is half what it was when they first tried to acquire Yahoo! Every company is being hit by the recession, and exaggerating the stock price drop of Yahoo! while downplaying other companies’ stock price drops is the same kind of hype that’s *causing* the reductions in stock prices in the first place.
I also love how Microsoft refused to agree on, and other people seem to love attacking Yang for, an employee protection plan that would preserve employee rights and permit graceful and smooth transitions in the event of a mass layoff by Microsoft (a tactic they are well-known for).
Haha, the “Most Embarrassingly Overhyped Launch” is so true! Cuil was such a let down!
Vanessa,
He wasn’t referring to whether or not Metallica should be paid, but rather how they conducted themselves in the process. You don’t take on one ideology and represent yourself that way, then, as is convenient, change your stance. If you do, the the public has the right to judge your behaviors, which in this case would appear to be “bait and switch”.
Thanks for the list! Some that I missed there throughout the year and had a chuckle.
As for the Yahoo! takeover – considering it was quite apparent to anyone who was paying attention where the stock prices (for everyone) was going, it seems like a bad idea for Yahoo’s shareholders that Yang did not sell out at a high price. And if Yahoo! continues to lose market share like it has, I’m not sure if their employees are all that safe anyway. At least a buyout might have put money in their pocket (via employee share purchase plans, etc.)
Surely some of our British data breaches should have been given an honary mention in “Most Embarrassing Data Investigation”. Our government’s lost discs, memory sticks and laptops all over the place in the last 12 months.
Stumbled
@Jon Massey and @KevFrost, the British government definitely had some strong contenders that could have easily snagged a spot. Do rest assured, though, that those bloopers haven’t gone unnoticed here:
Hi, We’re the Government, and We Lose Computers
Memo: Please Erase All Memories of Lost Memory
Unreal stuff, isn’t it?
Metallica’s new album is freaking brilliant and hey, them freaking out about Napster is in the past. So what if they defended what is rightfully theirs?
I’d hardly call Larz’ latest video embarrassing..much to the contrary, actually.
Great list BTW, never heard of Cuil b4 and had to laugh about the Lively incident.
Great read, I really enjoyed that.
I agree that Jerry practically sunk yahoo into the ground when refusing microsoft’s offer. 48 billion was it?
Stumbled!
Cheers
Eric from Wheels and Wood
Great read indeed!!LOL
Great article even though I don’t agree with it all.
Ouch! My fave is still the subway hack story because they actually dug in deeper when they tried to dig out. Us motocrossers know that’s what happens everytime, and you have to accelerate through the mud and ignore it to make it out.
Thanks for using my brother’s photo in number 6 about the TSA. I asked Rodney to hold my camera while I checked my flight. He took that shot and I posted it to my Flickr account. When I discovered your article on Friendfeed today I sent Rodney a link.
Here wrote back “Blah Blah Blah why don’t they get to the point and just say Photo by Rodney Limprecht.”
http://flickr.com/photos/russell_reno/3118366909/
Great post! Hopefully, next time you’ll include one of your own embarrassments…
Metallica should be embarassed, but nothing mentioned in this list is really their fault. Their previous actions were ugly and stupid, this year they seem to have learned from those mistakes. That’s actually a good thing.
The guy they canceled the interview with had written in his paper about how the EDITED versions of tracks he had downloaded (that were not yet released legally) were better than the actual tracks. I listened to these tracks, and the editing is a joke. Considering that, the article he wrote was basically a fuck-you to them, and I don’t blame them for what they did. Surprised it was spun this way? Not exactly.
As for the previews of their record, almost all of them were positive and there was never any reason to ask them to be removed. Metallica learned of this after the fact and reversed course on that. There’s no reason to ban previews where people say “Metallica rocks better than ever in the last 15 years,” it had to be frustrating to find out such positive reviews about you were being banned.
They should be embarassed. But I don’t think they’re lying. We’ve seen plenty of good examples of online marketing of music this decade and their own missionmetallica.com site stands among them. They embraced the internet and downloadable music and it probably benefited them greatly.
I understand the hate and I’m on board with it but it just aint fair to base it on lies.
metallica was last relevant for prepubescent boys in the early nineties. It amazes me that people still listen to that schlock or care what its windbag members have to say.
Good post ……
But, I think you went a too hard on Jerry.
And Metallica deserved that.
What Andy said ^
There’s a difference between “embarrassment” and “something I don’t like”. Apparently the author of this piece is not aware of that.
Excellent article
Metallica part cracked me up it’s so true and little Lars .. lol
Thanks for the Great post,and gr8 collection
They forgot OS X10.5.6 Bricking machines when it was “upgraded” to.
Great post, although i gotta say that for the most over-hyped embarrassment i would have said that Sony’s ps3 home takes the cake here, this “amazing online interactive service” is a joke imo, people are just walking from one place to the next not doing much at all…
I don’t normally read “Top X” lists on blogs but your intrigued me and I’m glad I read it.
Nice article, very informative and interesting.