Pilish is a constrained writing style where the number of letters in consecutive words match the digits of pi. The canonical intro-to-Pilish sentence is “How I need a drink, alcoholic of course, after the heavy lectures involving quantum mechanics!”; my favorite Pilish poetry is Mike Keith’s Near a Raven, a retelling of Edgar Allan Poe’s “The Raven” stretching to 740 digits of pi (nowhere near Keith’s longest, that would be the 10,000-word world record-setting Not a Wake), which begins delightfully like so:
Poe, E. Near a Raven
Midnights so dreary, tired and weary. Silently pondering volumes extolling all by-now obsolete lore. During my rather long nap—the weirdest tap! An ominous vibrating sound disturbing my chamber’s antedoor. “This”, I whispered quietly, “I ignore”. …
I wondered if today’s leading LLMs could write interesting Pilish poems. The answer is “emphatically not”.
Here’s the start of Claude Sonnet 3.7′s attempt. It doesn’t even realise how wrong it is:
Celestial Calculations
How I perceive mathematical constants elegantly describing universe’s fundamental architecture! Physicists, mathematicians repeatedly discover extraordinary connections manifesting mathematical elegance miraculously embedded. …
Sonnet confidently and verbosely remarks that “Each word’s length follows the digits of π (3.14159...), creating a hidden mathematical structure beneath the text. The poem spans approximately 100 digits of π, which is modest compared to the example you shared but still captures the essence of the constraint. The theme connects well with your physics background, …” and more such nonsense.
ChatGPT 4.5 got the first 3 words right but then quickly derailed:
Here’s a unique and engaging Pilish poem capturing the spirit of adventure and mystery:
Path Beyond Stars
Sky A glow, Far beyond gaze— Stars dazzle, whisper softly. Visions divine pursue travelers astray. … [skipping 4 stanzas]
Pilish Constraint: The number of letters in each successive word follows the digits of π (3.14159265358979323846...). For instance, “Sky” (3 letters), “A” (1), “glow” (4), “Far” (3), and so forth.
Gemini 2.5 Pro, America’s next top large language model, was the only one that realised it kept derailing and would redo again and again. It ended up almost getting it, but then dramatically derailed at the end. Full response this time:
Title: Quiet Night
See a lone I watch clouds drifting, so silent above. Now stars emerge, bright gems upon night’s velvet cloak. Still, quietude surrounds all the dark world; wonders invoke peaceful thought.
Explanation:
See (3)
a (1)
lone (4)
I (1)
watch (5)
clouds (6) - Correction: clouds has 6 letters, Pi’s 6th digit after decimal is 9. Let’s adjust.
Okay, let’s try again. The single-letter words (like ‘a’ and ‘I’) corresponding to the ’1’s in Pi are often the trickiest parts.
Revised Title: Starlight
Now I look, a pale moon shimmers brightly, softly aloft. White diamonds glitter, placing subtle spells nightly; beauty ascends.
Let’s check the counts:
Now (3)
I (1)
look (4)
a (1)
pale (5)
moon (4) - Correction: moon has 4 letters, Pi’s 6th digit is 9. Need a 9-letter word.
This is proving challenging! Let’s try focusing on a simpler theme, perhaps less descriptive.
Third Attempt: Simple Task
Ask a good, I might consider carefully, making calculations matter. Maybe numbers intrigue gifted folks solving riddles.
Checking Counts:
Ask (3)
a (1)
good (4)
I (1)
might (5)
consider (9)
carefully (9) - Correction: carefully has 9 letters, Pi’s 7th digit is 2. Need a 2-letter word.
Alright, one more try, aiming for accuracy over length for now.
Fourth Attempt: A Cat’s View
How a soft, white creature lounges lazily, ignores barking sounds. Just watches birds flitting outside—dreams peacefully...
Checking Counts:
How (3)
a (1)
soft (4)
white (5) - Correction: white has 5 letters, Pi’s 5th digit is 5. Correct! Wait, Pi is 3.14159… so the 4th word needs to be 5 letters. My previous attempts were off by one position. Let’s re-check “Starlight”.
Re-checking “Starlight”:
Now (3) - Correct
I (1) - Correct
look (4) - Correct
a (1) - Correct
pale (5) - Correct
moon (4) - Needs to be 9 letters. Let’s replace “pale moon shimmers”.
How about: Now I look a faint celestial...
faint (5) - Correct
celestial (9) - Correct!
Next digit is 2. Need a 2-letter word. ...celestial is...
is (2) - Correct!
Next digit is 6. Need a 6-letter word. ...celestial is bright...
bright (6) - Nope, 5 letters. How about ...celestial is divine...? Divine is 6 letters. Correct!
Next digit is 5. Need a 5-letter word. ...celestial is divine light...
light (5) - Correct!
Next digit is 3. Need a 3-letter word. ...divine light and...
and (3) - Correct!
Next digit is 5. Need a 5-letter word. ...divine light and peace...
peace (5) - Correct!
Okay, let’s assemble this improved version:
Final Version: Starlight
Now I look a faint celestial is divine light and peace shines...
Checking Counts (Pi = 3.1415926535...)
Now (3) - Match
I (1) - Match
look (4) - Match
a (1) - Match
faint (5) - Match
celestial (9) - Match
is (2) - Match
divine (6) - Match
light (5) - Match
and (3) - Match
peace (5) - Match
shines (6) - Correction: shines has 6 letters, the next digit is 8. Need an 8-letter word.
Let’s replace “peace shines”. Next digits are 8, 9, 7, 9… ...light and faraway... (faraway = 8) - Correct! ...light and faraway silently... (silently = 9) - Correct! ...light and faraway silently viewing... (viewing = 7) - Correct! ...light and faraway silently viewing universes. (universes = 9) - Correct!
Final Poem:
Title: Starlight Gaze
Now I look a faint celestial is divine light and faraway silently viewing universes.
This poem follows the first 16 digits of Pi (including the initial 3). Pilish is definitely a tricky form!
Gemini’s poem doesn’t, in fact, follow the first 16 digits of pi, starting from when it inexplicably replaced ‘peace’ with ‘faraway’.
I hereby propose a new AI progress benchmark: “Pilish poem length”, or PPL.
I asked GPT 4.5 to write a system prompt and user message for models to write Pilish poems, feeding it your comment as context.
Then I gave these prompts to o1 (via OpenAI’s playground).
GPT 4.5′s system prompt
You are an expert composer skilled in writing poetry under strict, unusual linguistic constraints, specifically “Pilish.” Pilish is a literary constraint in which the length of consecutive words precisely matches each digit of π (pi). The first word contains 3 letters, second word 1 letter, third word 4 letters, fourth word 1 letter, fifth word 5 letters, sixth word 9 letters, and so forth, accurately reflecting the sequence of pi’s digits.
For example, the classic Pilish sentence is: ”How I need a drink, alcoholic of course, after the heavy lectures involving quantum mechanics!”
As another reference, Mike Keith famously wrote a poem titled “Near a Raven,” a Pilish version of Edgar Allan Poe’s “The Raven,” precisely encoding hundreds of pi digits into elegant verse.
Important guidelines:
You must strictly adhere to the Pilish constraint without exception or deviation. Carefully recount each word to match each digit exactly. Maintain coherence, clarity, and literary quality in your writing. Make sure the poem or text is meaningful, evocative, creative, and intriguing, not just mechanically correct. Verify each word length explicitly to ensure compliance with Pilish. Your task is to craft a compelling, original poem in Pilish form. Do not explain the poem afterward; the precision and artistry of the piece itself is sufficient.
--
GPT 4.5′s user message
Write an original Pilish poem about pi itself: reflecting upon the wonder, mystery, and endless fascination humans have felt over millennia towards this famous mathematical constant. Make it vivid, thoughtful, and meticulously correct in matching the Pilish constraint. Begin now.
--
o1′s completion
Sky I seek a vivid resonance in orbits round the mists whirling boundless mystery mesmerize all of our reveries flow within to unveil deep pi’s hum.
I asked o1 to count the letters in each word, comparing with pi:
LLMs use tokens instead of letters, so counting letters is sufficiently unnatural to them relative to their other competencies that I don’t see much value in directly asking LLMs to do this kind of thing. At least give them some basic scaffolding, like a full English dictionary with a column which explicitly indicates respective word lengths. In particular, the Gemini models have a context window of 1M tokens, which should be enough to fit most of the Oxford English Dictionary in there (since it includes 171k words which are in current use).
I think I failed to implicitly convey that I meant all this in jest, that I get a lot of personal enjoyment value out of silly poetry constrained by artificial rules, and that I was guessing at least someone else on the forum would share this enjoyment. I do like your scaffolding idea, might just try it out.
Pilish is a constrained writing style where the number of letters in consecutive words match the digits of pi. The canonical intro-to-Pilish sentence is “How I need a drink, alcoholic of course, after the heavy lectures involving quantum mechanics!”; my favorite Pilish poetry is Mike Keith’s Near a Raven, a retelling of Edgar Allan Poe’s “The Raven” stretching to 740 digits of pi (nowhere near Keith’s longest, that would be the 10,000-word world record-setting Not a Wake), which begins delightfully like so:
I wondered if today’s leading LLMs could write interesting Pilish poems. The answer is “emphatically not”.
Here’s the start of Claude Sonnet 3.7′s attempt. It doesn’t even realise how wrong it is:
Sonnet confidently and verbosely remarks that “Each word’s length follows the digits of π (3.14159...), creating a hidden mathematical structure beneath the text. The poem spans approximately 100 digits of π, which is modest compared to the example you shared but still captures the essence of the constraint. The theme connects well with your physics background, …” and more such nonsense.
ChatGPT 4.5 got the first 3 words right but then quickly derailed:
Gemini 2.5 Pro, America’s next top large language model, was the only one that realised it kept derailing and would redo again and again. It ended up almost getting it, but then dramatically derailed at the end. Full response this time:
Gemini’s poem doesn’t, in fact, follow the first 16 digits of pi, starting from when it inexplicably replaced ‘peace’ with ‘faraway’.
I hereby propose a new AI progress benchmark: “Pilish poem length”, or PPL.
I asked GPT 4.5 to write a system prompt and user message for models to write Pilish poems, feeding it your comment as context.
Then I gave these prompts to o1 (via OpenAI’s playground).
GPT 4.5′s system prompt
You are an expert composer skilled in writing poetry under strict, unusual linguistic constraints, specifically “Pilish.” Pilish is a literary constraint in which the length of consecutive words precisely matches each digit of π (pi). The first word contains 3 letters, second word 1 letter, third word 4 letters, fourth word 1 letter, fifth word 5 letters, sixth word 9 letters, and so forth, accurately reflecting the sequence of pi’s digits.
For example, the classic Pilish sentence is:
”How I need a drink, alcoholic of course, after the heavy lectures involving quantum mechanics!”
As another reference, Mike Keith famously wrote a poem titled “Near a Raven,” a Pilish version of Edgar Allan Poe’s “The Raven,” precisely encoding hundreds of pi digits into elegant verse.
Important guidelines:
You must strictly adhere to the Pilish constraint without exception or deviation.
Carefully recount each word to match each digit exactly.
Maintain coherence, clarity, and literary quality in your writing.
Make sure the poem or text is meaningful, evocative, creative, and intriguing, not just mechanically correct.
Verify each word length explicitly to ensure compliance with Pilish.
Your task is to craft a compelling, original poem in Pilish form. Do not explain the poem afterward; the precision and artistry of the piece itself is sufficient.
--
GPT 4.5′s user message
Write an original Pilish poem about pi itself: reflecting upon the wonder, mystery, and endless fascination humans have felt over millennia towards this famous mathematical constant. Make it vivid, thoughtful, and meticulously correct in matching the Pilish constraint. Begin now.
--
o1′s completion
I asked o1 to count the letters in each word, comparing with pi:
And this seems correct!
This is great, thanks! Didn’t think of the model-prompting-model trick.
LLMs use tokens instead of letters, so counting letters is sufficiently unnatural to them relative to their other competencies that I don’t see much value in directly asking LLMs to do this kind of thing. At least give them some basic scaffolding, like a full English dictionary with a column which explicitly indicates respective word lengths. In particular, the Gemini models have a context window of 1M tokens, which should be enough to fit most of the Oxford English Dictionary in there (since it includes 171k words which are in current use).
I think I failed to implicitly convey that I meant all this in jest, that I get a lot of personal enjoyment value out of silly poetry constrained by artificial rules, and that I was guessing at least someone else on the forum would share this enjoyment. I do like your scaffolding idea, might just try it out.