[ExI] Riddle?

[BillK]

On Mon, 28 Apr 2025 at 04:37, Stuart LaForge via extropy-chat
<extropy-chat at lists.extropy.org> wrote:
>
> This is a question I posed to ChatGPT (free version). It took it 5 wrong
> guesses and about 4 additional clues before it finally solved it: "What
> is the name of the town wherein dwells the baddest man whose name begins
> with last letter of the country west of Spain?" I thought it was
> something of a Trivial Pursuit question, but ChatGPT called it a
> fantastic "riddle". Heh.
>
> Show me what you got, humans! ;)
>
> Stuart LaForge
> _______________________________________________


Gemini 2.5 Pro Preview 03-25 got the answer in 9.2 seconds.
It went straight to the song.
BillK


Gemini 2.5 Pro -

Here's my thought process for solving this riddle:

Deconstruct the Request: I need to find the name of a town. This town
is where a specific man dwells. This man is described as the "baddest
man". His name begins with a specific letter. That letter is the last
letter of the name of the country west of Spain.

Identify the Country West of Spain:
Look at a map (mental or actual).
Spain is on the Iberian Peninsula in Europe.
The country directly west of Spain, sharing the peninsula, is Portugal.
Find the Last Letter of that Country's Name:
Country: Portugal
Last letter: L
Identify the "Baddest Man" whose Name Begins with that Letter:
The letter is 'L'.
The description is "baddest man". This sounds like a specific phrase
or character, likely from a song, story, or folklore.
"Baddest man" immediately brings to mind the song "Bad, Bad Leroy
Brown" by Jim Croce.
The character's name is Leroy Brown.
Does his first name start with 'L'? Yes, Leroy.
Is he described as the "baddest man"? Yes, the lyrics famously say
"Baddest man in the whole damn town".
Determine the Town Where this Man Dwells (according to the source):
The source is the song "Bad, Bad Leroy Brown".
Listen to or recall the lyrics of the song.
The relevant line is: "Bad, bad Leroy Brown / The baddest man in the
whole damn town / Badder than old King Kong / And meaner than a
junkyard dog... / Now Leroy, he gamble / ... / He got a .32 gun in his
pocket for fun / He got a razor in his shoe / ... / Well the south
side of Chicago / Is the baddest part of town / And if you go down
there / You better just beware / Of a man named Leroy Brown."
The song explicitly places Leroy Brown on the "south side of Chicago".
Formulate the Answer:
Country west of Spain: Portugal
Last letter of Portugal: L
Baddest man whose name starts with L: Leroy Brown (from the song)
Town/Area where he dwells: The south side of Chicago.
The question asks for the town. While "south side of Chicago" is a
part of a city, Chicago is the city/town. The song specifies the area
within the town. Chicago is the most direct answer to "name of the
town".

Final Check: Does the answer fit all parts of the riddle?
Name of the town? Chicago.
Wherein dwells the baddest man? Leroy Brown (the "baddest man in the
whole damn town") is associated with the south side of Chicago.
Whose name begins with...? Leroy starts with L.
...the last letter of the country west of Spain? Portugal ends in L.
Yes, all conditions are met.
---------------------------------------------

Answer -

Let's break this down:
Country west of Spain: That's Portugal.
Last letter of Portugal: That's L.
The baddest man whose name begins with L: This refers to the character
Leroy Brown from the Jim Croce song "Bad, Bad Leroy Brown". The lyrics
call him "the baddest man in the whole damn town".
The town wherein he dwells: According to the song, Leroy Brown is from
the south side of Chicago.
So the town is Chicago.
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