8. Holland Play (GTA IV)
This is another one that may turn some heads, but it’s a significant mission in GTA IV. This is one of the first times you get to decide who lives and who dies (in a major way). At this point you have been working for Playboy X and for Dwayne Forge, two old friends. At some point, Playboy will ask you to kill his mentor, shortly Dwayne will flip the table.
This isn’t a particular challenging mission, but it is an emotional one. Playboy has been paying you (very handsomely as well) and helping you out through the game, but it is clear that both Nico and Dwayne are a lot more alike and develop a friendship (if you care for that kind of thing in the narrative) so it’s really a choice between money and friends, and either way, it turns out to be quite an emotional conundrum.