I first fell in love with the GTA series during the "Waste the Wife" mission early in Vice City. Okay, this probably makes me seem like some kind of psycho misogynist. Fondly remembering how much I laughed while driving Tommy Vercetti around to kill some arm-waving, shrieking bimbo via vehicular homicide certainly won't win me any fans over at NOW.
But it wasn't so much the fact that Tommy was killing a woman as much as he was killing, well, anybody without any reference to scruples or setting up justification for the assassination by making the woman evil incarnate. This payphone murder for something like $200 really hammered home Rockstar's go-nihilistic-or-go-home philosophy, and made it clear to me that videogames would never be the same again. There were no attempts to soften what good old Tommy got up to on the Ocean Boulevard strip, making the game's brutality freeing and honest. For the first time, I felt like I was playing a totally adult game where zero concessions were made for kiddies.
I haven't felt quite the same way about any of Vice City's successors. While I'm still a capital-F GTA Fanboy, both of the major sequels in San Andreas and GTA IV have left me a teensy bit flat, as have the two PSP games, Liberty City Stories and Vice City Stories. All of the games hooked me in one way or another, and I don't regret playing them in the least. San Andreas is still probably my number-two favorite game of all time next to Vice City, and I spent so many hours with Liberty City Stories on the PSP that I have the wrists of a porn-addicted septuagenarian.
Still, each of the GTA games after Vice City has gotten progressively more genteel. Well, at least as genteel as games about carjacking and killing for fun and profit can ever be. San Andreas gave us a hero we could almost admire in CJ. Just about every criminal act he committed had some sort of silver lining. Even his most Vercetti-like act--burying a construction worker alive in a porta-potty--was done in defense of his sister's honor. In the end, CJ wound up playing 007 for James Woods and then freeing his neighborhood from crack. Tommy, on the other hand, would have likely shot Woods in the face instead of flying that Harrier and helped cook up the crack in the kitchen of his Starfish Island mansion.
Same deal with both Liberty City Stories and Vice City Stories. The former had you playing Toni Cipriani, a generic mobster who seemed to only kill even worse goombahs with vowels at the end of their last names; the latter saw you guiding Vic Vance, who was more of a plain old wannabe drug dealer than a hardened sociopath you could really grow to love. Both were all about the same dastardly deeds, although they took the edge off every atrocity by making the victims much worse than the protagonists. Just about everybody that you offed absopositively deserved to die. Horribly.