Sim Bastard, or Jones in the Jerk Lane
Basically, you start out with a blank Dude, your job is to climb your way to the top, using the people around you as rungs on the stepladder to success. You need to cheat, bribe and threaten your way through university, funded by your junior management position at the local Burger Hut, then work your way up the corporate ladder, hacking, slashing and burning bridges as you go, undermining those pesky do-gooders and avoiding the blade from other roving Bastards, on your journey to the top. On your way, you need to get the biggest condo, filled with all the most expensive, tasteless stuff you can find, drive the biggest cockmobile you can get and manage a string of mistresses without your trophy wife finding out. The game ends when your empire inevitably crumbles around you and you choosing between enduring an expensive show-trial before spending the rest of your life in maximum security or a bullet to the brain.