The Most Embarrassing Tech Keynotes of All Time, Ranked

Having a product fail to do the thing it’s supposed to do is not the only way to embarrass yourself during a keynote presentation, but it’s the most tried-and-true method. Even Steve Jobs fell victim to the dreaded demo fail at one point or another. No demo, however, has failed as simply and elegantly as Honda’s Asimo robot.

Contemporary viewers are numb to the sight of Boston Dynamics’ unnerving, acrobatic robot dogs engaging in complicated exercises. But in 2006, the presentation of Asimo walking up a simple set of stairs was an event. Unfortunately, no one remembers the historic first step that Asimo took into the future. No one remembers the second step either. But the third step, the one that was followed by a comically perfect fall has become legendary.

Asimo’s stiff, oh-shit-energy is at the heart of the slapstick, but it’s his little head swivel before ascending the staircase that makes this such a classic. It’s as if he’s turning to look you dead in the eyes before he completely blows it.

When Elon Musk first showed off the Cybertruck in 2019, he touted the strength of its “Tesla Armored Glass” in an effort to bolster the vehicle’s image as a rugged, futuristic urban tank. Musk then asked an employee to come out and throw a metal ball at the Cybertruck’s window. The result of the stunt was the first time that the mythical model failed to live up to its promises. It likely won’t be the last. Since then, the dream of Cybertruck production beginning in 2022 appears to have faded away.

While this should be a cut-and-dry case of hubristic showmanship turning into an embarrassing failure, Musk’s social media trolling and internalization of the concept that there’s no such thing as bad publicity allows him a certain level of plausible deniability. Grimes’ ex-boyfriend has since gone on to bring out an actor in a latex suit to demonstrate Tesla’s future plans for a humanoid robot, so there’s really no way of knowing how low he’ll go in his efforts to make you ask the question: Troll, vaporware, or both?

Tech demos for home appliances should be fairly boring affairs. But in 2018, LG’s Vice President of Marketing, David VanderWaal, made the mistake of relying on his company’s CLOi voice assistant to add a little razzle-dazzle to his product presentations. What followed was the exec dutifully powering his way through the proceedings while CLOi gave him the silent treatment.

Many tech titans have fallen into the trap of anchoring their presentations to a spotty voice assistant, but VanderWaal’s time in the barrel is especially unbearable due to the sheer length of its discomfort.

The long, strange trip of music-annotating startup Rap Genius came to an ignominious end late last year when it was finally acquired for less money than investors had sunk into it over nearly a decade. But in 2013, the company was riding high and its founders’ antics were the biggest news to come out of that year’s TechCrunch Disrupt.

This conference appearance was the birth of the performative Cool Guy Tech Bro. Execs Tom Lehman, Ilan Zechory, and Mahbod Moghadam took the stage wearing shades and prime hipster gear of the time and yammering on about how “turnt-up” the process of launching a business has been.

Okay, this is more of a Q&A than a keynote presentation. I would argue, though, that the Rap Genius boys came to Disrupt to make a one-way presentation of their own obnoxious attitude. This was an announcement that the future leaders of tech wouldn’t be introverted hoodie-wearing math geeks, they’d be more like a guy you watch your drink around at the club.

You can draw a straight line from this event to the kind of NFT fans who complain that no one at the airport complimented their Bored Ape hoodie.

Despite its reputation for perfectionism in design and relentless protection of its public image, Apple boasts a litany of screwups in its storied history of keynotes. It’s tempting to highlight a Steve Jobs flub because he’s well known for his Type-A cantankerousness, but I want to direct your attention to the moment when Apple’s VP of software engineering Craig Federighi, the man in charge of the feature, showed off the iPhone’s Face ID feature for the first time.

Prior to Apple’s big 2017 event, there were some privacy concerns around the anticipated addition of Face ID to the iPhone X. No one, however, predicted that it just wouldn’t work.

“Unlocking it is as easy as looking at it and swiping up,” Federighi says in the video as he looks at the phone and swipes up. But the feature fails. Then it fails again. To his credit, Craig very smoothly switches to a backup model that works and he laughs it off. But the failure did little to give people assurance about Apple’s security claims.

When the feature was finally available to the public, many folks had a hard time getting Face ID to work properly. I have vivid memories of my partner screaming “witness me” at her phone for weeks. Eventually, Face ID’s performance improved—just before we all started wearing masks.

Rap Genius walked so that these douchebags could run.

In addition to being an adept director of migraine-inducing action flicks, Michael Bay is also an experienced conpitchman. He got his start directing commercials and has personally starred in ads for companies like Verizon. For a price, he’ll gladly hawk whatever bullshit you’re looking to sell, but he draws the line at unprofessionalism. When people are unprofessional on a Michael Bay set, someone might get killed. After Samsung’s 2014 CES showcase, I can’t say for sure that Bay didn’t personally murder someone behind the scenes.

The director lasted for less than a minute on stage. In the clip, he’s asked what inspires him and that’s when the trouble starts. “As a director what I do is I try to...” Bay says before exasperatedly lets out a big sigh and spins in place. He explains that there’s some trouble with the teleprompter before making a short attempt at winging it.

Bay quickly apologizes to the audience and runs off stage. To his credit, the Armageddon director knows that bouncing might be better than deviating from corporate-approved copy.

The folks at The Verge have already designated Qualcomm’s 2013 CES event as “the most insane keynote ever” and they’ll get no argument from me. This one only comes in at number 2 on our list because I think there’s one presentation that’s more embarrassing.

The clip above will give you an idea of the absurd fever dream that Qualcomm brought to CES that year, but you really should watch the full video if you want to descend into the depths of a marketing exec’s extended existential cry for help. It includes an interminable skit between hip actors playing the roles of “the Socialite, the Gamer, and the Entrepreneur.” Big Bird shows up, as does Desmond Tutu and Maroon 5. Guillermo Del Toro invites Qualcomm’s Executive Chairman over to his house for Mexican food. Microsoft’s Steve Ballmer, king of unhinged keynotes, takes the stage at one point just to be sure he’s present for the two most infamous keynotes in history. And it all wraps up with a showcase for the upcoming film Star Trek Into Darkness, the most cursed of all Star Trek movies.

That’s right, I told you Steve Ballmer was coming. The Windows 95 launch event is not only the most embarrassing keynote of all time, it’s the most iconic. To the tune of the Rolling Stones’ “Start Me Up,” Microsoft’s fearless leaders, already among the richest men in the world, lose their damn minds and dance like no one’s watching. But we were watching and there was no way to unsee it.