GTA 1 on PS1. First heard about the top down car theft game with screenshots in Saturn Magazine. Never released for Saturn so had to buy a Playstation. The later sequels & expansions never really held the same gameplay or originality. Of course when GTA 3 came out and everybody from tv stars to footballers were playing GTA it was time to move on. Perhaps a 3D top-down HD Edition on XBLA/PSN of the original GTA with gfx/models etc from the later games would work well as a crossover from Retro to Modern.
The original top down affair was a great little game. But when i saw Vice City on my mates Playstation II i was blown away, practically bought a PSX2 that weekend just for Vice City, one of the few games my wife totally loved as well.
Played that game a TON ! Great soundtrack, some really good missions, was always a good laugh to see how many police stars you could get and see how long you could survive for. An exceptional game. Went back to play GTA III after i completed Vice City, was good but much preferred Vice City.
Now have GTA III on my ipod which is great. But an exceptional game