Someone got ChatGPT to roast Apple's executive team — and the results are hilarious

Apple iOS wwdc 2023
(Image credit: Apple)

Generative AI is the fad that simply won’t go away, and beyond real-world uses in generating content for businesses, tools like ChatGPT can also be quite funny, and we might just have found the best example yet. 

iOS developer Steve Moser asked ChatGPT to roast Apple’s leadership, bringing with it some absolutely brilliant barbs. All in jest of course. 

It looks like Moser used an old image to prompt the response because it still shows Angela Ahrendts as Apple’s SVP of retail, even though she departed the company in 2019. Hilariously, ChatGPT-4 actually declined to help with the prompt the first time around, and only delivered after being advised that it was just some “lighthearted” fun and that it was viewing a painting, rather than real people. 

Executive roast

The LLM said “remember, this is all in jest” before showing absolutely no mercy to the magnificent seven.  

Here are the roasts:

  • Craig Federighi: That hair looks like it’s been designed in Cupertino and manufactured in a wind tunnel - if you think hard enough this is technically a compliment. 
  • Eddy Cue: Always ready for a surprise keynote feature. “And one more thing… my eyebrows!” - Eddy Cue did not deserve this, “one more thing” was a nice touch though.
  • Luca Maestri: The kind of guy who’d use a spreadsheet to track his smile frequency  - ChatGPT not hesitating in reaching for the “accountants are boring” trope. 
  • Dan Riccio: Rocking the “I Just invented a new gadget but forgot where I put it” expression. - Maybe now we know who left that iPhone 4 in a bar all those years ago. 
  • Philip W. Schiller: Looks like he’s auditioning for the next superhero role: Captain Marketing! - Admittedly, a much snappier title than Senior Vice President Worldwide Marketing. 
  • Jeff Williams: The smile says “friendly neighbor”, but the eyes say “I know the secrets of the next iPhone”. - Sounds like the tag line for a very tame horror movie.  
  • Angela Ahrendts: She’s got that “Retail? I thought this was the line for the runway!” look. Again, assuming they mean a catwalk, this actually sounds like a compliment.

The curve of generative AI remains impressive and has clearly come a long way since we asked Bing to imagine WWDC 2023 as a wrestling event. Apple is considered to be quite behind when it comes to generative AI and large language models like ChatGPT. A recent report revealed Apple was caught “flat-footed” by the explosion of these tools and is now spending millions of dollars a day to try and catch up. 

Most recently, it has been reported that Apple plans to use AI in tools like Siri and the Messages app, as well as Xcode, Apple Music, Pages, and Keynote. If you don’t want to wait for that, there’s already a way to replace Siri with ChatGPT on your iPhone instead.

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Stephen Warwick
News Editor

Stephen Warwick has written about Apple for five years at iMore and previously elsewhere. He covers all of iMore's latest breaking news regarding all of Apple's products and services, both hardware and software. Stephen has interviewed industry experts in a range of fields including finance, litigation, security, and more. He also specializes in curating and reviewing audio hardware and has experience beyond journalism in sound engineering, production, and design. Before becoming a writer Stephen studied Ancient History at University and also worked at Apple for more than two years. Stephen is also a host on the iMore show, a weekly podcast recorded live that discusses the latest in breaking Apple news, as well as featuring fun trivia about all things Apple. Follow him on Twitter @stephenwarwick9