How many times have you beat this game..?
I'm on my fourth play-through...
I have no enemies. I don't permit such a thing. -Anton Chigurh
Too many times to count. All with 100% completion. Same with the other GTA games. This one is among my most favorites. The replay value is awesome and Tommy Vercetti rules!
shareShankster is spot on. Even several years later, this still presents itself as the best GTA game of the bunch.
I've beaten the game about a dozen times, usually with about 75% completion. I've played it on the PC most (easier to aim headshots, very important) but have done a few on the PS2 and the Xbox 1 as well. Once I bothered to sit down and find all the bonus stuff to get 100%... very tricky but worth it!
It has to be at least 6 times - since the last two times I played, I got 100% from complete memory (OK the b.f. helped me remember where specific packages were). If we can remember where they ALL are - then yeah I've played a lot LOL
I'm trying to finish up 100% in San Andreas right now and it inspired me to consider making a master file for VC as it's the only one where I feel I can do 95% of the side-stuff before doing a single mission (with the only thing not truly possible is the 4 heli-checkpoint races and possibly the vigilante since I use either a tank or hunter)