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The Most Awkward Moments in Tech

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Technology may shape the world we live in today, but there are many tech lovers who still consider themselves a bit awkward. But it isn’t just the fans that can be bit “socially uneasy” – plenty of moments within the industry have made us cringe over the years. Here are some of the most toe-curling.
Technology may shape the world we live in today, but there are many tech lovers who still consider themselves a bit awkward. As someone who once told a room full of people that playing Vampire – The Masquerade: Bloodlines was the most memorable moment of my life, it’s a stereotype I can relate to. But it isn’t just the fans that can be bit “socially uneasy” – plenty of moments within the industry have made us cringe over the years. Here are some of the most toe-curling.
Editor’s Note: This feature was originally published on July 24,2017. We’ve bumped it as part of our #ThrowbackThursday initiative because the more time passes, the more awkward and funny to watch these videos become.
Mark Zuckerberg may exude confidence today, but in this 2010 interview with Walt Mossberg and Kara Swisher, the Facebook CEO is so uncomfortable that he appears to be slowly liquefying. As he rambles on for minutes without saying much, his urge to run away becomes painfully obvious. The agonizing time it takes to remove his microphone is pretty awkward, but not as much as when Swisher suggests he’s running a cult.
While the previous two entries were as amusing as they were awkward, this one is so difficult to watch it may cause your bones to curl inwards. In Michael Bay – director of big-budget Hollywood action movies like Transformers and Bad Boys – it seemed that Samsung had landed a major start to promote its curved televisions at CES 2014. But things went from bad to awful very, very quickly.
As Bay made his way onto the stage in front of the gathered journos and industry professionals, he had the demeanor of a man who would rather be somewhere else. Less than a minute into the presentation, he loses his place on the teleprompter. At this point, Bay announces he’ll “wing it,” while no doubt wishing he could just jump inside the TV he is failing to promote.
After wringing his hands so much they’re in danger of turning to dust, Bay abandons all semblance of composure when he’s asked how the curve of the TV will impact viewers. “I’m sorry,” apologizes the director as he scuttles away, Zoidberg-style, leaving Samsung exec Joe Stinziano to optimistically ask the crowd to give thanks for the one minute and 10 seconds he was on stage.
If there’s one name you could always rely on to make your jaw drop in a mixture of shock, horror, and a little bit of awe, it was Steve Ballmer. The former Microsoft CEO’s numerous antics mean he makes more than one appearance on the list, but this is a personal favorite.
It was at a Microsoft corporate event in 2000 when Ballmer took to the stage with the energy of a man who’d just snorted every gram of cocaine the 1980s produced (he hadn’t). Managing to find a perfect combination of sweaty enthusiasm, wild-eyed terror, and full-on aggression, his performance doubtlessly inspired employees, who at this point were probably fearing for their lives if they didn’t show similar levels of adoration.
As Ballmer enters a Berserker-like frenzy, you’ll notice that even the injury he suffers around the 0:25 mark doesn’t slow him down. When he’s finally finished bouncing around and screaming, he takes to the podium – possibly hiding a huge heart attack – and proclaims: “I LOVE THIS COMPANY. YEEEEEEAAAAAHH!”
The event is a moment that will live on forever in the annals of tech history. It was recently parodied in HBO’s Silicon Valley when Jack Barker mimicked the routine on stage at Hooli-Con.
U2 may have sold over 150 million albums worldwide, but, partly thanks to the antics of frontman Bono, they’re catching up on Nickleback in the ‘most disliked band’ category. So, what better way to regain the popularity they enjoyed in the 80s than to force their new album onto half a billion iTunes users’ accounts.
At the iPhone 6 unveil event on September 2014, U2 made a surprise appearance on stage. The Irish rockers proceeded to announce that their new 11-track album was being made available to anyone with iTunes – for free!
After less than 1 percent of iTunes users had chosen to download the album, Apple decided people simply mustn’t realize what an amazing opportunity they’re passing up. In a piece of marketing that can only be described as “drunken,” the company decided to make the downloads automatic.
Strangely, an awful lot of people didn’t appreciate the turgid, middle-of-the-road ‘Songs of Innocence’ – which received tepid reviews – barging its way onto their various Apple devices. In what must surely have felt like a very awkward move on Apple’s part, the iPhone maker had to create a webpage explaining how to remove the album. But the most gut-churning moment was perhaps Bono’s explanation of why the band went through with it:
“Drop of megalomania, touch of generosity, dash of self-promotion and deep fear that these songs that we poured our life into over the last few years mightn’t be heard.” Thanks!
Incidentally, Tim Cook’s painfully awful “Rawk” devil horns/high five with Bono deserves an entry of its own.
What’s worse than publicly promoting your company’s product and having it all go wrong? When that company is Microsoft, and you’re Bill Gates, that’s what. Note how Gates feigns amusement while Conan O’Brien laughs at him as the technology he’s praising repeatedly fails.
Way back at CES 2005, Gates shared the stage with the talk show host. The billionaire was trying to show off the ability to operate Windows Media Center using a remote control. But the only thing he managed to do was squirm awkwardly in his chair while the elusive slideshow refuses to appear.
Further attempts to run the program prove just as futile. You can almost see Gates internalizing his murderous fury as O’Brien repeatedly tries to make light of the situation. Still, at least he could call on one of Media Center’s product managers to reveal the software’s full potential, but the Blue Screen of Death had other plans.
We’re firmly back into 100 percent awkwardness territory with this one. Qualcomm’s keynote at CES 2013 is so difficult to watch, there’s a very real danger of your skeleton jumping out of your body to escape the horror. There’s a good reason why it’s called “the most awkward event ever.”
Assuming you make it past the actors whose parts may have been written by the physical manifestation of the “How do you do, fellow kids?” meme, what better way to tone done the uncomfortableness than by bringing Steve Ballmer onto the stage?
The tragedy continues as the kind of people you would definitely expect to see at a chip manufacturer’s event are rolled out: Guillermo Del Toro, the Archbishop Desmond Tutu, Alice Eve – from Star Trek Into Darkness – and Big Bird.
For the final cherry on the cake, Maroon 5 closed proceedings. But due to Qualcomm not securing a license to stream the band, the webcast viewers were treated to silence, then Dido.
Ballmer makes another appearance on the list, though this time the awkwardness is a result of his smug laughter and horribly incorrect predictions about this so-called iPhone thing. Shortly after Steve Jobs unveiled the first iPhone, Ballmer complained that the device’s lack of keyboard made it unappealing to businesses and “not a very good email machine.” The statement came back to bite Ballmer in the ass on numerous occasions, especially after what became of Microsoft’s Windows Phone endeavors .
Almost a decade later, Ballmer said Apple convincing carriers to subsidize the iPhone was the reason for its success “I wish I’d thought about the model of subsidizing phones through the operators,” he explained last year.

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