Grand Theft Auto: Vice City
There is a lot to do in Vice City. I'm really impressed by the amount of content here. I'm also really impressed by how poorly some of it is implemented. When you've got a game that has so many options, it's inevitable that a bunch of them end up not working too well. But there is enough good in the game that playing it is still damn fun.
Progress: Wiseguy (2013), finished main missions