10 Video Game Enemies You Felt REALLY Bad For Killing

If you didn't feel even the faintest flicker of emotion while taking down Dark Souls' Sif, the Great Grey Wolf, you might want to talk to a professional.

For starters, Sif is one of the most unique and straight-up awesome-looking bosses in the entire series - a colossal wolf which holds its dead partner's gigantic sword in its mouth.

Despite doing nothing more than guarding the tomb of its dead pal, Sif is a mandatory boss who must be killed in order to obtain the Covenant of Artorias.

To make matters even more unpleasant, players who whittle Sif's health down will eventually be met by the sight of the poor creature limping and whining before you finish her off.

And that's not even the end of the story - Dark Souls' DLC throws players a few hundred years back in time, where they're able to encounter and fight alongside a younger Sif, further underlining just how awesome she was, and how terrible it was that you "had" to kill her.

On the off-chance that you end up playing the DLC before fighting Sif, Sif will even acknowledge your prior friendship in the later boss fight, while still insisting that her partner's grave must be protected.

FromSoftware aren't exactly known for getting the tear ducts flowing, but this? This was brutal. Prepare to Die Edition? More like Prepare to Cry Edition.