Grand Theft Auto: Vice City

In order to perform a headshot you must aim your gun at an enemy or civilians head and shoot, this is most easily done with one of the two sniper rifles in the game. You will likely unlock this trophy through natural progression depending on your play style, if not then you can easily grind it at the end of the game. I found the easiest location to be at the Vercetti Estate on Starfish Island. You can find a Sniper Rifle in the hedge maze on the Western side of the mansion. You can then proceed to headshot all the gang members in the property, they will not shoot back at you and there are lots of them around making for easy pickings. You will attain a wanted level but the cops shouldn't be able to find you inside the property. You can track your progress by pressing the and navigating to Stats => Number of headshots.