Things that would suck if it happened IRL.

jail tycoon, rape D:

Go to sleep! :>

Negative mouse acceleration.

Creepers

The Calamity

Death from old age...I don't want to die!

Phrase?
This comes to mind:
"Tell me kid...you ever danced with the devil by the pale moonlight?"

Dark Souls - Moonlight Butterfly.

Fuck that boss.

What a fun topic. Well, one I feel like is forever burnt into my memory - Floaters from Fallout 2. Prince of Persia's(The first one because it's the only one I've played) enemies are pretty horrifying. Area 51 had those horrifying bug-like things that exploded on contact. Seriously, fuck those things.

death.

Getting handcuffed and having your pants stolen, then getting force feed a rotten banana.

All of Spec Ops: The Line

:/

Zombie Apocalypse.

Clicky

AM has selected you.

(from "I have no mouth and I must scream", AM is a supercomputer that selects 5 people to torture for over a hundred years, while having destroyed the rest of the world. Being killed seems like the better option in that scenario.)

Gear up, we're going in! CSGO

GTA

I'd like to go out on a date with Dante as Kat, but considering Limbo and all the demonic monsters, not even such a hot love is worth it. I'll pass. :'I I think.

Any competitive FPS ever.

"Feel the wrath of Shao Kahn" - been playing Mortal Kombat 9 recently, and still get brutally murdered by that guy even on easier difficulties way too often :/
"Nuclear launch detected" from Starcraft would also be rather unpleasant, given that you only hear it when you're on the receiving end.

Get shovel!

In fact anything Fidel says in Jagged Alliance 2 would be terrifying.

Lose 7:1 at semi-finals in Fifa 14

DOOR STUCK

DOOR STUCK

Gone Home. It would be like purgatory, except everything would be overpriced and all you could do is walk around and read about terribly written teenage lesbian angst. :^)