
Having a browse through xkcd, noticed the alt-text on this one which says
Wikipedia trivia: if you take any article, click on the first link in the article text not in parentheses or italics, and then repeat, you will eventually end up at "Philosophy".
This is what I got:
Random Page -> en.wikipedia.org/wiki/Edward_Atkyns_Bray
-> en.wikipedia.org/wiki/Poet
-> en.wikipedia.org/wiki/Poetry
-> en.wikipedia.org/wiki/Literature
-> en.wikipedia.org/wiki/Fiction
-> en.wikipedia.org/wiki/Narrative
-> en.wikipedia.org/wiki/Story
-> en.wikipedia.org/wiki/Sequence
-> en.wikipedia.org/wiki/Mathematics
-> en.wikipedia.org/wiki/Quantity
-> en.wikipedia.org/wiki/Property_%28philosophy%29
-> en.wikipedia.org/wiki/Modern_philosophy
-> en.wikipedia.org/wiki/Philosophy
Mind was blown.
EDIT: If I'd spent a tenth of the time researching this instead of actually testing it, I'd have found this a lot sooner: en.wikipedia.org/wiki/Wikipedia:Get_to_Philosophy
( , Sun 5 Jun 2011, 16:44, Reply)

not always. Television gets you caught in a non-philosophical loop, for example.
( , Sun 5 Jun 2011, 16:53, Reply)

en.wikipedia.org/wiki/Mangles_family also leads to Philosophy.
( , Sun 5 Jun 2011, 16:55, Reply)

leaves you in a loop about the Ancient Greek language.
Edit: Actually, it's possible I used a bracketed link I just realised.
( , Sun 5 Jun 2011, 17:08, Reply)

It does actually work with Rob Deering. I can't believe I spent so long doing that though.
( , Sun 5 Jun 2011, 17:12, Reply)

started off with en.wikipedia.org/wiki/Lur%C3%B8y
( , Sun 5 Jun 2011, 17:25, Reply)

I ended up at the XKCD page through a clever route. Think someone had been fucking with it though.
( , Sun 5 Jun 2011, 17:47, Reply)

en.wikipedia.org/wiki/Ian_Huntley
you get stuck in a loop about the Latin language.
( , Sun 5 Jun 2011, 17:47, Reply)

I got
Soham - Town - Human Settlement - Archaeology - Human - Extant_Taxon - Biology - Natural Science - Science - Knowledge - Fact - Information - Sequence (as above on to Philosophy).
( , Sun 5 Jun 2011, 17:59, Reply)

Looking back I clicked on Latin, which was in the middle of a parenthesised sentence, instead of living (extant_taxon).
( , Sun 5 Jun 2011, 18:31, Reply)

I can imagine a lot of exceptions to be water tight.
( , Sun 5 Jun 2011, 18:19, Reply)

But I got stuck on a Craft-Vehicle loop on the 6th try.
( , Sun 5 Jun 2011, 17:49, Reply)

I just invented a "see how quickly you can get to hitler from any wikipedia article" game... spooky. Umbrellas = 3 steps.
( , Sun 5 Jun 2011, 18:05, Reply)