GRAND THEFT AUTO / Rockstar / PC
The very first Grand Theft Auto game stirred up nearly as much controversy upon its release as Grand Theft Auto 3 did. The game has basically everything that the later titles would, just on a smaller scale and in a two-dimensional world seen from a bird's eye view. In this one, you actually get to choose from a few different characters, and are dropped off in Liberty City to make your way as a freewheeling criminal.
This one has a story mode that allows you to progress from Libery City to Vice City to San Andreas, but unlike later titles, you don't have to accept missions to complete it. Moving forward in the game is simply based on how much money you have, so it is theoretically possible to simply bring cars to the chop shop, wreak havoc and find bonus Rampages to earn enough to progress the game (this is difficult, however, as you earn comparitively little this way, and the goals to progress are some pretty high dollar amounts).
The game is obviously a bit more limited than the later 3D installments, but still quite a bit of fun. The play control and physics are fairly solid (albeit not necessarily realistic) and there's a decent range of missions (though a few too many rely on phone-booth hopping in a tight time limit, which is irritating). One major annoyance with this one is that there is really no save/continue option - once you've unlocked a new city, it is always available, but leaving the game means you have to start the whole string of missions in that city from the beginning, and if you die or are arrested during a mission you simply have to eat the financial loss and continue on.
The version available for download from Rockstar contains the radio stations, and is thus a 300 MB download. There are versions floating around at various abandonware sites that have the radio stations stripped out which are only about 30 MB, but otherwise are complete and work just fine. Just throwing that out there for the low-bandwidth users out there.