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i did some thinking and none deserve a second game in my opinion. although i havent thought of everything (im not a gta or storytelling expert), i believe their stories have already been told and it would be lazy to just use the same protagonist again. it would be insanely hyped, mostly for nostalgic reasons, and then people who ignored the redundancy initially would be outraged at how poorly it turned out.
aside from that, and not that im a writer or anything, but i cant think of a good way to do it (gta3 universe protags onward). maybe a prequel since otherwise it would just be a rehash of the same rise to glory the characters already went through. however, their personalities have already been established and they wouldnt have the same sort of appeal as it did the first time you started getting to know them in the original game. in many cases, in a prequel or sequel youd already pretty much know what to expect of the character.
so about prequels...
should they make one about claude with a voice (no) and how he ends up losing it in a climactic gunfight?
should they once again return to the liberty city setting (no) where cj was living a clean life in 1990-ish before moving back to san andreas?
tommy had been in prison for 15 years... so backtrack to 71 when he killed 11 people in liberty city (according to wikipedia. i couldnt remember off hand). it seems like an ok idea to make a prequel out of that but there are some pros and cons that stick out. i think the cons outweigh the pros unfortunately. pros -early 70s liberty city setting (and everything that comes with it: music, cars, etc.) -opportunity to show a different side of tommy before he undoubtedly changed through 15 years of prison cons -liberty city again (eh.. 70s makes a bit of a difference so whatever) -...mafia again? -could ray liotta pull off a younger voice? i KNOW people would rage if they used a different voice actor. -tommy could possibly be too young for a fully entertaining game to be made of his early life -the big one.. how would they end it? tommy gets thrown in jail and were left to just go play tired old vice city again? or they end it before he kills the 11 guys and is sentenced to 15 years, and what happens to him is never shown.. he just ends up in prison for killing only 11 people. there are plot holes. that whole thing is silly in the first place, seeing as you kill hundreds, if not thousands of civilians and law enforcement and spend a whole 30 seconds in jail once you get busted in-game.
i could go on but like i said, they were either too young or lived a clean, unremarkable life for a prequel, or their stories have already been told and their appeal is too thin for a sequel. thats just what i think. i dont wanna start any heated arguments or some crap.
tl;dr - no because nostalgia. if anything, just do a remake.
The NPCs players kill that aren't story related are non-canon and don't count. Also Ray Liotta would want way too much money to return, at least more than what Rockstar would likely be willing to pay. Not as it matters since they're not going to revisit that era.
Tommy Vercetti in modern time
Modern day Tommy would be in his early to mid-60s if not older depending on release year for a game that's taking place in the present.
Band/Artist I've been listening to way too much: Fallon Bowman/Amphibious Assault. https://soundcloud.com/fallonbowman