The first game to bear Sid Meier's name right in the title (having attained fame for designing a number of strategy games in the early '80s), Pirates was also a relatively unique game in its time. A sandbox title set in the Caribbean during the age of piracy, you begin by picking a time period, nationality and one of five skills to have (Fencing, Navigation, Gunnery, Medicine or Wit and Charm), and from there you're pretty much left to your own devices. You can hunt pirates for bounties, become a privateer for any of the four major powers or a freelance pirate, raid towns, seek lost treasure hauls, or any combination of the above. Once you choose to retire your character (or are forced to due to advancing age), your exploits are totaled up and you're given a score and rank depending on how well you did. The best score is only available if you've acquired a mighty sum of land and money, done well enough with a nation to become a King's Advisor and married, but there's no infallible strategy to employ owing to the randomized nature of the game - the locations of treasure fleets change constantly, towns constantly get raided by different nations and change ownership accordingly, and finding a specific pirate captain is a matter of luck even if you're aware of their whereabouts. Still, the game is a surprisingly fun and addictive experience meant to be played in bursts of an hour or two, still holding up surprisingly well today. It even retained enough of a following over the years to get two remakes - a 1993 version called Pirates Gold! which adds some more content and overhauls the graphics, and a 2004 remake on XBox, PSP and PC that was more minigame-focused. My personal recommendation is the Genesis port of Pirates! Gold, which looks and sounds quite nice and plays wonderfully.
