Scariest: Maybe SCP: Containment Breach. I can't run Amnesia or even Slender.
Saddest: Shadow of the Colossus
Longest: Hm... I'd have to say Runescape as well. I spent an unhealthy amount of time on that game.
Scariest: "The House". I only get scared by jumpscares, which is why Amnesia don't scare me too much.
Saddest: I'd say Heavy Rain, but only saw a walkthrough, haven't played it. Red Dead Redemption.
Longest: Runescape... It was so addicting it's almost scary.
Scariest: Slender or Amnesia.
Saddest: Red Dead Redemption, Darkness 1 and 2.
Longest: 587 hours on TF2, 500 hours on CSS, 192 hours on Gmod, 131 hours on Skyrim. Also spent many many hours in Oblivion, but I don't know the exact number.
Scariest: Amnesia (Justine DLC was pretty ****ing scary)
Saddest: Red Dead Redemption (Possibly L.A. Noire, aswell)
Longest: No idea, really. I can't keep track of my Minecraft time, and I have a shitload of gametime on every TES game (Mostly Oblivion and Skyrim). I also played Pokemon for far too long, if you count all the games. I played Pokemon Emerald to death, and I probably have 200 hours on it.
Scariest: Silent Hill 2... *shudder*
Saddest: By saddest, do you mean most emotional or specifically saddest? Most emotional is definitely Bastion, but for saddest I'd have to go with Bioshock 2.
Longest: Probably Borderlands for total time spent, because I've played through it like 8 times with various friends. But 100 hours into one Skyrim save file.
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My name is Ozymandias, king of kings. Look upon my works, ye mighty, and despair.
Saddest: Red Dead Redemption really struck me. Scariest: Minecraft (thats friggin SSSSSSSSSSS, Man!) and In Fallout New Vegas when the Big mountain stealth suit kept talking to me. Longest you've spent on a game: Fallout NEw Vegas, Skyrim, Oblivion, Fallout 3 is the longest.