I've been in plenty of Monopoly games that dragged on for hours, with one or two bankrupt players sitting on the sidelines, bored to death. But a few intrepid gamers decided to figure out the shortest theoretically possible Monopoly game. Their solution is explained here and depicted in the video below. While extremely unlikely, it's theoretically possible that it could happen. It takes only nine rolls of the dice.
But what's more interesting is this comment thread in which several other Monopoly theoreticians propose slightly shorter games -- several eight-roll versions and even one seven-roll game. There's also a two-roll solution that involves a strategy known as "insane auctioning" which seems even more unlikely (since it involves a player making remarkably stupid choices when buying properties), but hey, it's theoretically possible so I say it's valid. There is also, of course, a theoretical "shortest game" in which one player simply defaults (typically by throwing the board across the room). That requires no rolls and is thus mathematically optimal. But let's be civil.
Anyway, here's the 9-move, 21-second game that started the discussion. Behold the nerdiness!
(Via Metafilter, which has its own awesomely nerdy comment thread.)