Wikipedia's Endless Pool Party (Not Quite What it Sounds Like)
There's no longer a question of whether the English-language Wikipedia will hit the four million article mark: only when. While new topics may become increasingly difficult to come by, five, six million or more articles is not out of the question. And when Wikipedians are not busy working on making that happen, sometimes they like to place guesses on when those things will happen. If you visit Wikipedia's vast backstage, you can find several current and past betting pools these milestones and others through the years.
One of the first was the Half-million pool, in June 2004, in which several dozen editors took part. When Wikipedia passed 500,000 articles on March 17, 2005 the winner (an active Wikipedian to this day) had guessed March 18, narrowly beating another who had guessed March 15. Since then, more recent pools have focused on landmarks including the Million pool (passed March 1, 2006) and the 300-million edits pool (a matter of dispute, but certainly in 2009). Though there are just more than 3.5 million articles today, if you'd like to guess when Wikipedia's four-millionth article will be created... I'm afraid you're out of luck. No further guesses were taken after February 2010.

Among pools still open, one of two versions of the Five-million pool is still open, as is the Ten-million pool and the Twenty-million pool. In the latter category, one unlucky soul guessed 2007, several picks would have this achievement within the next decade, but more have placed their bets in the 2015-2025 range, and more still in the 2026-2100 range. A few have placed their bets on "Never"; time will tell... or not.
There are some more outlandish pools as well, including something like a dead pool: the Last topic pool. What will be the last article created on Wikipedia? There are some swell guesses; among my favorites are: "2100 Wikimedia server room fire" and "Why the zombies won".
Want in on the fun? You can test your powers of prediction at Wikipedia:Pools. And if you do win, what exactly do you win? Is there any money involved here? Alas, no. Each page makes sure to note: "The person who comes closest to the actual date is the winner (of eternal fame)."
Photograph by Finlay McWalter, via Wikipedia.