I came late to the party because I only played GF in 2003. I was in a game store with my little brother and he wanted to get the game because he thought the cover was interesting. I remember telling him how stupid it looked like and how the game would no doubt suck. The image of Manny holding the DOD flyer made me think it would be some kind of sales simulator in which you have to keep selling more stuff to becomer richer and get better jobs etc.
My brother never really played the game because he couldn't speak English at the time, so the game was stored away and forgotten. He only took it out some time later when he had formatted his computer and realised that he couldn't re-install most of his games because he had lost the discs. I happened to walk by when he was talking with Eva in the beginning of the game, and I was sold on the spot. The writing was so hilarious.
GF remains my favourite game of all-time, though I'm no longer as active in the community as I used to be.