GTA III made a good go at portraying a heartless Hitman for hire with a personal vendetta.
Vice City had a street smart mafioso start a criminal empire in a new city. Forming new connections and developing businesses.
GTA IV (my favourite) was GTA III reincarnated in a "realistic" HD world.
---------San Andreas Spoilers!!!----------
San Andreas though...you never know what's up, first CJ is a gangster then a business owner (while working for the triads) then a secret super agent and before going back to being an über gangster he turns into Danny Ocean while f***ing with the mafia.
CJ's character and personality never convinced me of this infinite ability to be whatever needs to be. He's easily the dumbest of all the protagonists and has a hypocritical holier than though morality. Reluctant on being a cold hearted hitman but being fine with killing for his friends/gang.
All in all San Andreas is a great game, the universe is amazing, it's just CJ.
Edited by Bi0ha2ard_q8, 08 June 2013 - 09:30 AM.