All three of my favorite games do this, as do a few others (Tales of the Abyss. Akzeriuth. That is all). For sheer breadth and depth of emotion, though...
Tsukihime. Nothing else came close (except Type-Moon's other big work, Fate/Stay Night).
Creeping horror? When I first found out the consequences of being at the school at night, or not looking for Satsuki in the alleyway.
Stark terror?
<color=red>"Destroy. Destroy. Destroy. Slowly, completely, gently beyond comparison, cruelly to the point of numbness, I'll violate your life. That's right. The instant I rip off your limbs, tear open your ribs and pull out your intestines, biting into your neck as you scream in agony, chewing through your eyes as I ignore your pleas for mercy and spreading your brains on the ground like butter...!"
Barely suppressed mirth? Choosing Hisui to be the subject of Shiki's erotic dream, and seeing her reaction when she wakes him up. Shocked epiphany? Crushing guilt? Three words: Hisui's True Ending. Sheer mind-screwing confusion? Pretty much the entire middle part of Hisui's route, with Shiki going batshit bonkers.
Tears? Oh geez, at least once per story route, and often two. The game's love and death scenes are superb, and they're always accompanied, and enhanced, by <url=http://www.youtube.com/watch?v=eFd_Hoo_xaw>this music. The scene close to the end of Ciel's route in particular, with her trying and failing to bring herself to kill Shiki, made me break down sobbing.
It's also the only work in any medium I can think of that actually made me burst into tears at a happy ending. I couldn't help it; it caught me completely off-guard, and it happened during the route of my favorite heroine, the one who really, really deserved one.
Mass Effect (not the dirty way) and Fallout 3. They had very heavy moral choices which made me feel good when in both games I could never and to this day be evil.
I just cannot believe nobody else has said this. In Metal Gear Solid 4 when...
Big Boss turns off an elderly Zero's oxygen tank and embraces him while flashbacks of Zero during Operation Snake Eater flash across the screen as he begins to asphyxiate and eventually die while Snake stands off to the side and watches.
I came this fucking close to crying. Seriously, This. Fucking. Close. And Dear god the music didn't help matters much either...
For me it was Final Fantasy 8. A lot of people tout Final Fantasy VII or IX as being the best of the PS1 era, but for me, FF8 was the best Final fantasy to date. The romantic sort of tragic futuristic storyline really got to me.
And at the end, when Squall gets hit with that Ice lance and is falling backwards over the edge of that platform with Rinoa reaching out to him and their hands almost touching as he falls away is one of the most powerful moments I've ever felt playing a video game. I remember literally feeling my controller slip out of my fingers onto the floor and tears welling up in my eyes.
Thats powerful storytelling and the reason why when Final Fantasy is the best in the business at what it does.
The Kaim/Lirum scene with the two kids, and the first dream "Hannah's Departure" from Lost Odyssey really got to me.
And Final Fantasy VI's Kefka most definitely. Because, well, he succeeded in what he wanted to do. He became a god. The fact that the bad guy won in a game pisses you off pretty bad, but It's Kefka. It's all good.
Kingdom Hearts is my favourite game series...EVER. Though Silent Hill 2 made me feel extremely sorry for James, the way they build him up as a character was...nothing short of excellent.
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