Tricky one, hmmm.....as far as strategy goes, Rome: Total War is my favorite. One game that really surprised me was Portal, a couple of years ago Valve actually gave it away for free to all Steam users IIRC and I'd heard it was good but man was that some of the most enjoyable 3,7 hours of my gaming life! One of the shortest PC games I've played but maybe the most concentrated amount of fun and fair challenge, great game! Haven't played Portal 2 yet though. SimCity 2000 is also an old favorite, had it on Mac back in the day, guess that counts since the Mac and PC versions were the same. Good thread BTW!
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