Manly Tears: Things That Made You Cry

[Yora]

Metal Gear Solid is pretty much "Manly Tears - The videogame franchise"

The plot and the characters are all rediculously over the top and many lines just completely cheesy, but the whole thing is exceptionally well written and the visuals and music work together perfectly.

The bosses are all very satisfying to defeat, but at least half of them are just so sad when they die.
I'd link some videos, but the scenes probably won't work without the whole background and if you have a PS2 it would spoil way to much of the uncertainties. Let's just say the survival rate of named characters is under 20%, and almost everyone dies full of regrets.