Generative AI is the trend that refuses to fade away, and beyond its practical applications in content generation for businesses, it can also serve up a good dose of humor. And now, we might just have stumbled upon one of the best examples of AI-generated wit.

It all started when iOS developer Steve Moser decided to have some fun with ChatGPT by asking it to roast Apple‘s top brass, in a lighthearted manner, of course. However, it seems Moser used an older image as a prompt, one that still listed Angela Ahrendts as Apple’s Senior Vice President of Retail, even though she departed the company back in 2019. The chatbot had initially declined to participate, but with some reassurance that it was all meant in good fun and that it was merely “roasting” a painting, not real people, ChatGPT-4 finally delivered.

The executive roast that followed was nothing short of hilarious, with ChatGPT showing no mercy to Apple’s top leaders. Here are some of the zingers:

Craig Federighi: ChatGPT compared his iconic hair to something “designed in Cupertino and manufactured in a wind tunnel” and hinted that this might be a compliment if you think about it hard enough.

Eddy Cue: The chatbot couldn’t resist poking fun at Eddy Cue’s eyebrows, playfully suggesting he’s always ready for a surprise keynote feature with an “And one more thing… my eyebrows!” line. Ouch, but the “one more thing” addition was a nice touch.

Luca Maestri: ChatGPT playfully labeled him as the type of person who’d use a spreadsheet to track the frequency of his smiles. It seems the bot wasn’t shy about leaning into the “accountants are boring” stereotype.

Dan Riccio: The AI hilariously compared Dan Riccio to someone who just invented a new gadget but forgot where they put it. It’s as if we now know who left that infamous iPhone 4 in a bar all those years ago.

Philip W. Schiller: ChatGPT’s take on Philip Schiller was particularly creative, likening him to a superhero auditioning for the role of “Captain Marketing.” That’s definitely a snappier title than Senior Vice President of Worldwide Marketing.

Jeff Williams: Jeff Williams, according to ChatGPT, sports a smile that says “friendly neighbor,” but his eyes suggest he holds the secrets to the next iPhone. It almost sounds like a tagline for a mildly spooky horror movie!

Angela Ahrendts: The AI playfully suggested that Angela Ahrendts has the look of someone who mistook an Apple Store line for a fashion runway. Assuming they meant a catwalk, this could actually be seen as a compliment.

In the end, it was all in good fun, and the AI’s roasts offered a light-hearted take on Apple’s leadership team. With humor and creativity, ChatGPT proved once again that it can serve up some entertaining content beyond its more serious applications.