6. Killing Playboy X Or Dwayne - Grand Theft Auto IV
I've read many people saying this was actually one of the easiest choices they ever made in the game, yet for me I'd grown pretty attached to both guys, so even though this decision was telegraphed a few missions prior, when it came time to act, I went back and forth. Playboy is the seemingly carefree young-blood who should you kill you're awarded his pool-table-equipped house, as he's gone to hit the great black ball in the sky. However should you opt instead for the "oh woe-is-me"-spouting Dwayne, your reward is just that of a cash sum. Although this cash-incentive to kill him somewhat mirrors Dwayne's character, in that he's an old gangster who's been through and seen too much - therefore waving cash at another problem will make it go away - he really warms to your character of Niko Bellic. Therefore should you decide to take him out, his realisation that the one person left in his life he thought he could trust is now trying to kill him, is pretty heartbreaking.