Holy overly long description, Batman!
#25) Grand Theft Auto: Vice City (PS2/PC/Xbox)
It's funny. Many gamers of my age utterly dismiss games that they could possible enjoy just because their self-consciousness about their own masculinity prevents them from enjoying anything that doesn't have coarse language and excessive amounts of virtual intestines continuously splattering across the screen. But I dismissed this game for years because it had those two things.
I don't shy away from violence or swearing; I've been foulmouthed and into action movies since kindergarten. It was just that every 18-rated game I'd played before Vice City had been a shallow turd with gameplay as an afterthought, and the "edgy" subject matter (Oooooh, guns and drugs!) as the main attraction. Including GTA III. So what the Hell was I supposed to expect? Certainly not well-written (and completely skippable) dialogue, an interesting cast of characters, an even more interesting setting, a great (albeit completely licensed) soundtrack, and good controls even outside the vehicle. But that's exactly what Vice City has to offer. Well, that and ethnic stereotypes and Scarface worship. (Sorry, old habits die hard)