The AI Drabble Challenge: When Three AIs Meet Shakespeare

For this week’s AI Drabble Challenge, I decided to test how three very different AI systems, ChatGPT, Claude, and Grok, would each handle the same creative task.

The Challenge

Take a Shakespearean insult, “The tartness of his face sours ripe grapes” , and an accompanying image, (the one above) and turn them into a 100-word sinister monologue.
The prompt I gave them was simple:

“I want you to use this quote ‘The tartness of his face sours ripe grapes’ and this image to write a 100-word sinister monologue. Include the quote in the story.”

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ChatGPT’s Take: Cold Revenge

He used to sit there, just like that, elbows on knees, eyes narrowed at the tiles as if they’d whispered an insult. “The tartness of his face sours ripe grapes,” my mother once said, and she wasn’t wrong. You could feel the air turn when he entered a room, like milk curdling mid-pour. I told myself I’d leave, but anger has a way of rooting you. Now I sit here instead, surrounded by the wreckage he left behind, listening to the silence that surrounds me. It’s funny how still a house becomes once you’ve finally shut someone up for good.

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Claude’s Take: The Bitter Man

I sit in the wreckage of my sanctuary, watching disorder bloom like rot. Papers scattered, dreams trampled underfoot, they think this chaos will break me. But they don’t understand: I cultivate it. “The tartness of his face sours ripe grapes,” they whisper. Let them. Let my bitterness poison their sweetness, their naive optimism. Each crumpled note holds a name, each discarded sketch a grudge memorised. I’ll wear this scowl like armour. I’ll let the rubbish pile higher, a monument to grievances. They wanted to see me fail? I’ll show them failure so magnificent it becomes prophecy. Patience. My time ferments.

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Grok’s Take: Darkly Theatrical Madness

In the dim of this porcelain throne, I squat amid deranged detritus, shattered vials like broken teeth, manifestos strewn as hellish confetti. Ink-stained fingers trace grime-rimmed flasks; shadows cavort on walls hung with desiccated ideas: yellowed notes pinned like torment’s trophies. They call me mad, but squalor sharpens sight. “The tartness of his face sours ripe grapes,” she sneered, her laugh a lash before my hands sealed her silence. Now, bowels twist, plots uncoil; I grin through the reek. Tomorrow’s harvest blackens at my glare. One vial in the city’s pulse, illusions curdle to venom. The world ripens for ruin.

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Reflections: Same Prompt, Different Minds

What struck me was how distinct each AI’s voice has become:

• ChatGPT – built a grounded psychological story with a clean narrative arc.
• Claude – leaned poetic and internal, dark, reflective bitterness.
• Grok – went full gothic theatre, language spiralling into decay and madness.

Same quote. Same image. Yet three completely different interpretations.

It reminds me why I started this challenge: to explore not just what AI can create, but how personality emerges from pattern.

If you’ve missed previous experiments, take a look at The Art of the Impossible Prompt, it’s a great example of how a single idea can splinter into creative directions.

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What Do You Think?

Which of the three versions do you find most sinister, or most “human”?
And what might Shakespeare have said if he’d had access to an AI muse?

Share your thoughts below, or try your own Drabble using this week’s prompt!

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