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By the time I looked at this, the end path had changed, as "Fact" now leads to "Truth" instead of "Information". How long until someone intentionally manipulates the chain?
I was using the 2011-07-22 set so the data's already a bit stale...
My first theory was to edit a few articles including one point of the post-Science chain before Philosophy so that it got into a loop and it looked like all of Wikipedia led to Trilateral Commission.
When I first read the xkcd comic, I was amused that the article on philosophy didn't lead to itself. (It got trapped in a 2-cycle.)

Then I noticed that this was only because of an edit someone had made earlier in the day...

the author doesn't capitalize his sentences. i didn't find it difficult to read and only noticed halfway through the article. supposedly, capitalized sentences are easier to read, so i wonder if i've been conditioned by the internet to find uncapitalized sentences easy to read as well. off-topic, but interesting.
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Just tested it for the hell of it, started with "FireFighter", thought it was random... and 30 clicks later landed on Philosophy! Fun stuff.
Tried the word Stupid... Just got stuck in a loop.

EDIT: Tried it again... Stupid - Philosophy = 11

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- I deleted that part of my comment to avoid a stoning lol...

But yeah I was thinking something like an excel read out of the words, and just a fun little engine that would let you test any word on the fly. Maybe even live stat tracking for popular words that updates daily, I just love the idea of these word relationships. But there is soo much room for deliberate tampering.

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At the risk of being downvoted, ultimately all links on Wikipedia lead to God.
Project HN: Identify all non-confirming Wikipedia articles and edit them to fit the pattern.
Community -> Living -> Life -> Physical body -> Physics -> Natural science -> Science -> Knowledge -> Fact -> Information -> Sequence -> Mathematics -> Quantity -> Property (philosophy) -> Modern philosophy -> Philosophy

It's kind of like zooming in on what it means means to be alive in this universe. The fact that it ends at Philosophy is profound glimpse into what it means to be a thinking entity in the universe.

If we ever meet Aliens from another part of the galaxy, they would no doubt form similar knowledge structures that would probably end up being exactly like this. Their Wikipedias would end at Philosophy as well.

I think it has more to do with how encyclopedia articles are formatted. The first sentence always describes the broader subject which the topic resides in. I view it more as zooming out from topics that matter, each time you do so you lose resolution and only see a fuzzier image.
If you make a claim, then answer it, and ask "Why" and keep doing that, then you will eventually get down to the response: "Because I said so" or "because that is how we observe it to be".

"The words and values we use to describe nature are all imprecise approximations, many are wildly wrong. We observe phenomena all around us, and if you try to describe what it is, and ask "why" enough times then you get down to the discussion of what frame of reference we use to observe the universe. We have a body of knowledge, and we tack on new observations onto that body, occasionally the body reforms and the philosophy changes. Every learner has a philosophy.

Philosophy is where the rubber meets the road in figuring out what our universe is. Is matter a particle or a wave or other, it depends on your existing perspective, your philosophy.

I think of philosophy as the point where people throw their hands into the air in despair and say "Fuck it, I can't break this down any further, figure it out yourself", at which point the famous philosophers have joyfully begun down that ill defined path without an end.

  When Plato gave Socrates' definition of man as "featherless
  bipeds" and was much praised for the definition, Diogenes
  plucked a chicken and brought it into Plato's Academy, saying,
  "Behold! I've brought you a man."
I think Diogenes really may have actually "got it".
No one really gets it, and that's why Socrates was the smartest man in Greece. He knew that he didn't know anything.

Cynics like Diogenes are just as dogmatic as anyone, but the truth they are dogmatic about is that there is no truth. It's still a conviction. Be cynical about cynicism and Diogenes looks just as dumb as Socrates, or anyone for that matter.

We all look dumb when we answer questions. This is why Socrates preferred to be the asker.

I think it has more to do with where people end the chain, http://en.wikipedia.org/wiki/Human_nature is after philosophy.

Community -> Living -> Life -> Physical body -> Physics -> Natural science -> Science -> Knowledge -> Fact -> Information -> Sequence -> Mathematics -> Quantity -> Property (philosophy) -> Modern philosophy -> Philosophy -> Reason -> Human Nature -> Thought ->... The fact that http://en.wikipedia.org/wiki/Panpsychism tends to be the last part of the chain before it repeats is just less interesting.

PS: I suspect that most articles can be reached by every other article so you can take just about anything and say it's the "root" article for the rest of Wikipedia.

Whoa. That's less interesting to people? Wikipedia is telling us it can think!
PS: I suspect that most articles can be reached by every other article so you can take just about anything and say it's the "root" article for the rest of Wikipedia.

Most articles can be reached by every other article, but not if you are only following the first link. You can make a case that anything on the chain that leads from Philosophy back to Philosophy is the root, but anything outside of that is going to be tough to argue, in my opinion.

With that metric Philosophy is just one of a chain that ~99% of articles link to, looking at this graphs science or math is probably going to have a lower average chain length.
This can be tested.

I assume requiring the path from the first word was only to provide an easily replicable rule. Create a rule which chooses the fifth word (and where fewer than five links are provided, choose the last). Then compare the results to the OP's.

> If we ever meet Aliens from another part of the galaxy, they would no doubt form similar knowledge structures that would probably end up being exactly like this.

That's a bold assumption. I think its arrogant to assume that 'knowledge structures' take one form, which is the one in our heads. Ever seen/read Solaris?

I would be interested to see the same thing done with Politics.

I suspect there may be a few abstract concepts that this applies to.

Bob Dylan -> 1960s in music -> Popular music -> Music genre -> Genre -> Literature -> Art -> Senses -> Physiology -> Science -> Knowledge -> Fact -> Truth -> Reality -> Philosophy
A lot of them do, but sometimes there are loops (Eg. Computer Science). If you make an exception, choosing the second link for example, then it will lead you to philosophy.
If you make exceptions indiscriminately it will lead you to anything.
Why philosophy? If you keep clicking, you actually end up in a loop: Philosophy -> Reason -> Human nature -> Thought -> Consciousness -> Mind -> Panpsychism -> Philosophy -> ...

I'd say, of the above, "mind", "thought", and "reason" are pretty basic -- you cannot have philosophy without a mind, for one (though you can probably have a mind without philosophy).

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Saying "you cannot have philosophy without a mind" itself is one of the many philosophical concepts of mind-matter dualism.
And saying what you just said is using reason.
Reason or intuition! That's another 'philosophical' problem!
Seeing as we humans ceated Wikipedia perhaps in an effort to define and describe everything there is, the product ends up filtered through the lenses of it's creators and in doing so we inevitably end up defining what it is to be human. I dont believe we can understand or describe anything beyond what it is we are. Wikipedia is essentially the accumulation of the collective knowledge of it's creators so what else should we expect it to be outside of the definition of what it is to be man. The attempt to collect and master the understanding of everything is afterall a philosophic endeavor. Done babbling now lol.
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You can try it for yourself: http://blago.dachev.com/wikidrill
That's great! Does it "crawl" wikipedia live?
The default first entry, "Human", doesn't even reach "philosophy" before the maximum of 50 steps is reached. Kinda blows a hole in the theory...
It does: Human -> Living -> Biology -> Natural Science -> Branch -> Knowledge -> Facts -> Truth -> Reality -> Philosophy
But which of the twelve has the lowest average length? The article points to 'science', but how would the number of steps graph look then?
Start: Wikipedia -> free -> artwork -> Aesthetics -> Philosophy. 4 clicks away.
It even worked when I tried "Stone Cold Steve Austin"...
I found a few that didn't go to philosophy back when the comic came out. My favorite: Han Solo -> Harrison Ford -> Han Solo...
What about other sites like www.conservapedia.com or www.rationalwiki.org?

I tried on conservapedia and kept winding up at Earth or stuck in a loop.

On Conversvapedia everything eventually leads to "Ronald Reagan".