Meta Ray-Ban Display fail wasn't the worst. These tech demos are more cringe.

You may love Mark Zuckerberg for everything he's built; you may loathe him with a passion for the same reason.

But just for a moment, when the Meta CEO stands on stage in his Meta Ray-Ban Displays and fails repeatedly to do the simplest possible task the AI-loaded glasses were designed to do — pick up a WhatsApp call — he's no longer Zuckerberg the great and powerful.

He's just a guy, standing in awkward silence in front of an audience of thousands, asking them to ignore a loud ongoing ringtone.

We've seen many of these tech fails in product demos over the years, the awkward moments that remind us we're seeing human beings struggle mightily in the arena of the demo gods. Sometimes they're sweet (Apple's Craig Federighi having to hang up on his mom while showing off a new OS), but mostly, they're awkward to the point of cringe.

Mostly, we're watching someone who wasn't the greatest presenter to begin with (what tech nerd is?) flailing when a flaw in cutting-edge tech upends a scene they've been practicing for as long as a high schooler practices a play. You'd be forgiven for feeling like a parent who wants to put the camera down at that point.

So yes, Zuckerberg's demo enters the tech fail hall of fame (and given that Apple won't even do live tech demos during its keynotes anymore, he can at least be applauded for giving it a shot). But it's still a rookie mistake compared to these gems from the history of tech.

1. Steve Jobs begs the audience for more WiFi

What tech nerd was the greatest presenter? You'd get little argument from anyone in Silicon Valley: Steve Jobs, whose keynotes thrived on a sense of intimacy with the audience. (I saw that firsthand many times, including the legendary 2007 iPhone unveiling, which had its own array of interesting moments).

But even the mighty Jobs could flail, or get furious. In 2010, he threw a camera that failed to connect to an iMac at a stagehand. And in the iPhone 4 demo above, Jobs spends uncomfortable minutes actually not talking to the audience, a rarity, while he tries to load the New York Times on Safari.

Later in the keynote, being Jobs, he proceeds to bug not a stagehand, but the entire audience, many of whom are tech journalists carrying mobile hotspots. He comes with receipts: "There are 570 WiFI base stations operating in this room" — before demanding everyone close their laptops and shut down their hotspots so the demo can work.

"The WiFi" is still a go-to excuse for tech demos that go wrong; we saw that during Zuckerberg's keynote. But this Jobs keynote is one case in which we can say the WiFi was to blame.

2. Elon Musk smashes a Cybertruck window

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"Funnier every time you watch it." That was Mashable's review of the 2019 demo when Tesla CEO Elon Musk went too far in trying to demonstrate just how tough the windows in his Cybertruck, then years away from production, would be.

Here's how it went down. The Cybertruck's lead designer dropped metal balls on plates of Tesla glass that didn't shatter. Then Musk insisted the designer throw the balls at the truck. Having put a hole in one window, he proceeds to double down, and the Cybertruck gets two bullet-like smash marks.

Which in retrospect, may be the first sign that the Cybertruck was destined to become a whole stainless steel bucket of fail — and it also seems an appropriate summary of how Musk has blundered his way through the years since then.

3. The Microsoft Surface freezes over

The infamous Windows "blue screen of death" may be no more, but its legacy lives on in Microsoft's best-known product fails. Most well-known: The time Bill Gates stood on stage next to a Windows 98 machine that crashed as it tried to daisy-chain too many USB devices.

But is that really a classic demo fail? Not at all; Gates had an out. "This must be why we're not shipping Windows 98 yet," he quipped.

To be truly legendary, a demo fail must fluster the demonstrator and mar the product's image in a very public way. And in the Microsoft annals, there's no greater example than Windows president Steven Sinofsky unveiling what the company hoped would be its iPad killer, the Surface tablet.

Sinofsky's problem was that he didn't get a blue screen of death; his Surface simply froze as he was attempting to "browse smoothly" on Internet Explorer. The next few seconds no doubt haunted his nightmares, and may haunt yours, as Sinofsky tried to brazen his way through the freeze by turning his tablet away from the audience. Yep, that'll work!

4. Google Gemini fails twice

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When it comes to demo fails in the AI era, Zuckerberg has a long way to go if he wants to challenge Google for the crown.

The search giant demonstrated this at Google I/O 2025, where a live translation demo produced what was until now the year's most infamous smart glasses fail. But the true awkwardness of the moment was tempered by the fact that the demo was described as "very risky" beforehand, and shut down the second it stopped working.

For true classic cringe, you need a product failing twice at the supposedly easy task it's asked to do, ideally with a spinning wheel moment where its software just hangs. That's what happened at a "Made by Google" event in 2024, where senior director of product Dave Citron tries to show off how his Pixel can look at a Sabrina Carpenter concert poster and figure out if there's space in his calendar for him to get tickets.

Gemini, Google's AI, seems to turn up its nose at the very idea; Citron's request vanishes, not once but twice. Notably, Citron finally gets it to work after invoking "the demo gods."

Memo to all executives who want to avoid this list: The demo gods may be fictional deities, but calling for their assistance certainly doesn't hurt.