Wow it only took 16 clicks to go to Alan Shearer (nineties soccer player) to philosophy.
Actually, I think it’s nicely evocative – perhaps it should be considered a strange loop.
However, if I start from philosophy, the first link takes me to rationality, which links to reason, which links back to rationality… And from consciousness, I go ‘mind’, ‘panpsychism’, ‘philosophy’…
Ah, yes, that leads to a trait-phenotype loop. Too bad.
Yes, Grasshopper, with some practice I think you’ll find they all lead to knowledge.
Avoid anything related to the USSR. It’s a 2 link loop (Soviet Union -> Constitution of the Soviet Union -> Soviet Union)
Yeah, Mathematics is now “out of the loop” after edits today - but it leads into the “Knowledge” loop now. Maybe some enterprising editor can get that one cleaned up. 
The first link in Reason is Faculty, which redirects to Sense and ultimately leads to Knowledge. My mistake was skipping Faculty and clicking on Mental Ability.:smack:
I can confirm that looking up goatse.cx leads to knowledge. (btw whatever you do, don’t enter that address into your browser)
I did it! Random article FTW!
From East Fallowfield Township, Chester County, Pennsylvania to Philosophy in 9 links!
Okay I tried again with a random article (Thanmanpillai Kanagasabai) and it took me fourteen links.
Huh? Here are all the civil law disambiguations - none of them have “list of country legal systems” as the first non-italics/parenthesis link.
Civil law (area) goes to Mathematics, which has been put back on the philosopher’s road.
Civil law (common law) doe the same.
Civil law (legal system) seems to have been just edited to get it on track… 
Hmm. This works in Finnish wikipedia as well - from “towel day” to “philosophy” in 16 links. If you start from the English article of “towel day” you end up in an Indo-European language -loop, on the other hand. Curiouser and curiouser.
Mathematics now gets to Philosophy via Quantity, Property (philosophy), Modern philosophy, Philosophy.
Well, I started on Erik the Red and got stuck on Theodiscus, as the first link on that article redirects back to itself. Brilliant.
I got from the random article Three Day Road, a Canadian novel, to Philosophy in 20 clicks, ending via the sequence that fiddlesticks described.
Eerily enough, Three Day Road is partly inspired by a Native Canadian soldier who was born in my hometown.
The reason it works is that the first few sentences in a wiki article usually place the article’s subject in a more general context. So, with a few deviations you get more and more general. “heavy metal” goes to “rock music” goes to “popular music” goes to “musical genres” goes to “genres” etc. etc. Since philosophy is the most general of all fields, it’s very likely you’ll eventually wind up there, barring loops.
Bender Bending Rodriguez got me there in c. 12 clicks.
Are we supposed to ignore the etymology/pronunciation part? Because I keep getting stuck in Ancient Greek -> Greek Language -> Greeks -> Greek Language -> etc.
Yeah ignore that, that should be in parenthesis. OP says to ignore everything in italics or parenthesis.
I started with Michael Jackson and 17 clicks later got to philosophy. It did take a spin through Knowledge first.
I think links in bold are OK – in which case, the first link from reason is rationality.