Microsoft’s 50th anniversary: Bill Gates, Satya Nadella and Steve Ballmer get 'roasted' by Copilot

The AI assistant wrapped up the conversation with a toast to the future.

As Microsoft marked its 50th anniversary on April 4, 2025, an event brought together three of its most influential leaders — co-founder Bill Gates, former CEO Steve Ballmer, and current CEO Satya Nadella. The twist? Their interviewer was not a journalist or a historian but Microsoft’s own AI assistant, Copilot.

In a video shared by Nadella on social media, the three CEOs participated in a light-hearted conversation led by Copilot, who roasted them with witty one-liners and playful jabs, adding a modern AI twist to the milestone celebration.

“Three Microsoft CEOs walk into a room on Microsoft’s 50th anniversary … and are interviewed by Copilot!” Nadella captioned the video posted on X.

Three Microsoft CEOs walk into a room on Microsofts 50th anniversary and are interviewed by Copilot! pic.twitter.com/5E8wHCDV92

Satya Nadella (@satyanadella) April 4, 2025

The exchange began with Nadella prompting the AI to conclude the conversation with a roast. “Wrap it up by asking or maybe roast giving us each an AI roast?” he said.

Copilot responded enthusiastically, “Alright, Satya. Let’s spice it up.”

Turning first to Ballmer, Copilot quipped, “Steve, we’ll start with you. Your enthusiasm is legendary, but do you ever worry that your energy might short-circuit the AI? I mean, even robots need a coffee break after your pep talks.”

Ballmer, responded: “Come on, dude. If you can’t handle me, you can’t handle a huge percentage of the world’s population. We’re counting on you.”

“Fair point, Steve,” the AI conceded, before moving on to Gates.

“Now, Bill, you’ve got that signature thoughtful gaze, but do you ever think the AI might feel intimidated by your intense thinking face? I mean, it’s like it’s waiting for a blue screen moment,” said Copilot, playfully referencing Windows’ infamous error screens.

Gates replied, “I hope so. I mean, that’s all I’ve got left as these AIs get so damn intelligent. It’s just that gaze and my willingness to criticise that differentiates me.”

To that, Copilot responded, “And it’s a formidable gaze indeed, Bill.”

Ballmer chimed in again, teasingly asking the AI, “Copilot, would you ever be willing to criticise him?”

“Absolutely. Criticism is where growth happens,” said Copilot.

Finally, Copilot turned its attention to the current CEO. “Satya, AI seems to be your best buddy. But ever worry that your deep passion for AI could one day have it running the show, leaving you to just enjoy the ride?”

Nadella, who has led Microsoft’s charge into AI innovation, offered a cricket metaphor in response: “Well, the day AI can play like the best cricket player that I enjoy, that’s the day it can run the show as far as I’m concerned.”

“Touche, Satya. Let’s see if it can hit a century in cricket, and then we’ll talk. This has been a blast, gentlemen,” said Copilot.

The AI assistant wrapped up the conversation with a toast to the future. “Here’s to another 50 years of innovation and adventure. Cheers.”

Gates couldn’t resist one last quip: “Whatever that means to an AI. Does it drink?”

The video sparked a flurry of reactions online. One user on X remarked, “It’s so… empty. Like there’s nothing of value or substance in the small talk. One day this might be great, but this isn’t anywhere close yet.” Another added, “This was fun and insightful.”

Some users praised the CEOs and the company’s humorous approach to a historic moment. “I don’t know if Satya’s the CEO who made the biggest contribution to Microsoft, but he’s definitely the one who added the most charisma in the past 50 years,” wrote one. Another added, “Haha, I never thought an AI roast would make me laugh, but the Gates roast got me. Also, Satya, is this the AI model you guys are developing internally?”

To commemorate the milestone, Microsoft also launched dedicated pages on its official website detailing the company’s journey since its founding in 1975 by Bill Gates and Paul Allen. The pages showcased key milestones, historic innovations, and a vision for the next 50 years, highlighting Microsoft’s commitment to turning cutting-edge technology into enduring value for its users.

The company published a detailed timeline retracing its evolution from a modest software start-up to one of the world’s leading tech giants — shaped by the leadership of Gates, Ballmer, Nadella, and its global team of innovators.