Well, honestly I don't have a whole lot of personal experience with the GTA series--I've always enjoyed the idea of it, but never got around to actually playing--except once. Back in the years of the PS2 I managed to get a copy of Vice City from a friend of mine at school that I had to, no shit, hide from my parents. Damn, was it hard but probably the most fun in any sandbox game I ever played at the time.
Really, the best moment I can remember from that time didn't really happen in game though I can blame the game for it anyways. I was staying at my aunt's house in the outer banks, sitting inside playing Vice City. After I entered to required cheats for a good time, I got hit by a car and heard my character say "Yeah, go fuck yourself you wise and beautiful woman!" which confused me. At the time, I had no idea the rudest word of all time was just uttered, and without the world of the internet at my fingertips, I had no way to know what it meant. So...next time my dad and I were talking, I casually threw it at him thinking it was no big thing. Oh dear, the naivety of those days were great--needless to say, he wasn't too pleased. It did get quite a few laughs from my cousins that were nearby after they saw that white face turn fire truck red, though.
Still, I think the most fun I've ever had on Vice City is just playing it without cheats--even though that's ridiculously difficult. On the bright side, I've now got a PS2 and that beautiful game in my hands again, so back to it.
Thanks for the chance, guys--can't wait to test out my (literally) brand new R9 280 on this beautiful game!