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If I'm going with the game I enjoyed most, it would be SOCOM II on PS2. Amazing gameplay, tons of content. Played hundreds and hundreds of "clan wars" on GameBattles.

If it's the game I think was the most influential, probably GTA III? I still remember getting that game not expecting anything. IIRC I got it during one of the Toys R Us B2G1 that used to be so hugely popular. I think I also got MGS2 in that sale. What a haul. Set the standard for open world games and GTA V is still just stupid popular to this day.