I've never played any GTA game and would like to try the series out. I believe the only systems I have that can play GTA games are my PS2 and my MacBook (can run Windows on it), so of Windows, PS1 and PS2 games, where should I start? I'd prefer PS1 or PS2 as I don't often play games on my MacBook (it's mostly at work, not so often at home.) Note that graphics aren't a huge deal for me - sure, I like good graphics fine, but old-school works for me too. Some of my favorite games are 2D.
Edit: all game systems I have: DS, GBA, Gamecube, N64, PS2 (and Wii after xmas)
Edit: all game systems I have: DS, GBA, Gamecube, N64, PS2 (and Wii after xmas)