I have tried playing GTA IV on PoL and Wine without luck. It works with every other game I have tried, including World of Tanks, Portal, Portal 2, Half-Life, BioShock, World of Warcraft, Garry's mod and more. In my tests I installed the game and then applied the 1.0.7.0 patch. Now I cannot get it to boot, always crashes with the only error message being the playonlinux one.
I also tried with Wine, to no avail. Whole install works fine, then will not launch from the desktop shortcut or the /home/.wine/drive_c/program files(x86)/rockstar games/launchgtaiv.exe
It actually almost worked with update 3, but couldn't start the game or even change screen resolution. Changing wine version to the one recommended in the wine directory caused an error saying GTA IV needs a sound card to run. Changing sound driver is not an option because it says that there are none, but only with anything but wine ver. 1.3.23
My Specs:
CPU - AMD A10-6800K
RAM - 4GB
GPU - 9600GT (2007 version) (512MB DDR3) (Proprietary Drivers)
HDD - 750GB hybrid drive