Planescape: Torment/YMMV

Alas Poor Villain: Ravel Puzzlewell is a horrible being, practically an incarnation of evil. The stories of her cruelties are legendary, and people are still afraid to talk about her, centuries after she disappeared for good. And yet...three times she tried to do an act of kindness, and each time it backfired terribly on her. Then there's the fragments of herself that she's left around, like poor old Mebbeth, a kind healer who helps you a great deal, should you ask for it. After Ravel's death, Mebbeth slowly fades away, filled with regret.
Complete Monster: The Practical Incarnation. Even an evil-aligned Nameless One will be disgusted by his actions.
Cult Classic: Essentially doomed to this, given that about seven months after this game came out, a sequel to a much simpler and more popular game came out.
- It didn't help that combat, Diablo II's bread and butter, tended to feel like an afterthought in this game.
Crowning Moment of Awesome: Talking the Final Boss to death.
- Several of the spell animations as well, specifically the Rune of Torment, or descriptions of what happens when you cast the spell, like Abyssal Fury.
Crowning Moment of Funny: Morte and hookers. And female zombies. And Annah. Well, just... Morte.

Morte: "Women are the reason I became a monk. And, uh, the reason I switched back."

- The entire scene where Morte first equips Ingress' Teeth. You have to see it to believe it (this requires some game tweaking).
- Vrischika describing the Sword of Wh'ynn (requires mods to see):

Vrischika: It's also known as the Cheater's Blade. Merely holding it aloft will win you the game.

Nameless One: Win me the...what do you mean?

Vrischika: [Narrowing her eyes] Oh come now, you know exactly what I mean. Buy the Cheater's Blade, you beat the game. It's that simple...

Crowning Moment of Heartwarming: Playing as a good character nets you a lot of these. Especially the "best" ending.
Crowning Music of Awesome: The Recurring Riff, and by extension, most of the battle music and the background music for The Very Definitely Final Dungeon.
- Most of the Leitmotifs, especially Deionarra's.
Dying Moment of Awesome: Your party members, when they try to put up a fight against the Transcendent One. Particularly Fall-from-Grace, who actually manages to damage him.
Epileptic Trees: The plot itself can give birth to umpteen, but in-game dialogue mentions an all-time great: that the Lady Of Pain, mysterious and godlike ruler of Sigil, who can banish lawbreakers to endless, eternal mazes (or just kill them by casting a shadow made of thousands of magical blades) for crimes like murder, treason or daring to worship her, is actually six giant squirrels wearing a cloak, a ring of levitation and an illusion spell.
- A popular fan one is that the Nameless One's original incarnation is Zerthimon. Despite the fact that the Nameless One appears as a human male, albeit covered in scars (not only on screen, but characters who bring up the Nameless One's appearance also describe him this way), and the game's creators have outright said that, while they don't * know* who he was, they do * know* who he was not, and he was not Zerthimon.
- The guy sending the Symbol of Torment spell? It's the DM.
Magnificent Bastard: The Practical Incarnation. Holy crap the Practical Incarnation.
Moral Event Horizon: There's a chance it will be crossed in the story's narrative. You have several opportunities to cross it yourself. Some past incarnations (Especially the Practical Incarnation, and apparently your first incarnation) crossed it already.
- Your first incarnation did not merely cross the horizon. He ran past it screaming, scissors in hand, baby entrails dripping from his open mouth, dead puppy wrapped uncomfortably around his genitalia, and killing everything in his in his path in such horrible ways that they envy the dead puppy. The first incarnation was not a nice person. A thousand lifetimes of saintly penance would not be enough to make up for whatever he did. He's the good-aligned incarnation. And he's the one warning you.
- The Practical Incarnation made Deionarra love him so her soul will be bound to him in death and force her to help him if he ever returns. It was his backup plan should he die in the Fortress of Regrets, which he did.
- You can cross it yourself in multiple ways, though particularly, shoving Morte or Annah into the Pillar of Skulls.
  - Unless you pull Morte back out afterwards. It's still pretty twisted, but not a Moral Event Horizon--especially since you suffer for it.
Nightmare Fuel: Don't let the general quirkiness fool you, there are a lot of highly disturbing things in this game; enough that this trope requires its own page.
Player Punch: Hoo boy, yes. In particular, trying to play one of the evil paths is akin to facing down an Olympic boxer with lead weights tied onto your extremities. If the player is not a Complete Monster, of course.
- If the Nameless One joins the faction of the Sensates, he gains access to their private sensorium. Within is a sensory stone entitled 'Longing'. In it are Deionarra's experiences, days before her death. And as the Nameless One, you experience both sides of the conversation (it being with the past incarnation Deionarra loved), and come to *know* its horror, especially as a good character. It is not so much a Player Punch as the Lady's Shadow of Player Punches. In the same private sensorium, you find a trap from the Paranoid Incarnation and the experience of being tortured by Ravel Puzzlewell with some interactivity. 'Longing' manages to be the worst of the three, by far.
Squick: The game gets really vivid and detailed in describing what happens when you pluck out your own eyeball and replace it with a magical prosthetic. Or when you bite off your own finger and use your Healing Factor to graft another to the stump. Or when you ask a woman who prepares dead bodies to cut you open and rummage around in your guts for magical items left by previous incarnations. Also, two words: "baby oil."
That One Level: The Rubikon Dungeon Construct. While completely avoidable, essentially a Bonus Dungeon, if you want to find Nordom or kill the Evil Wizard, you have to set it to 'Hard' difficulty and go through it... and it is basically 62 instances of the same room copied over and over and over, with one to three pain-in-the-ass constructs which are completely identical from room to room. After the cuteness factor wears off, you can be forgiven for just going on a mad dash through the thing without stopping to fight.
The Woobie: Many, many characters in this story.
True Art Is Angsty: Though it has at least an equal share of humor, it owes the critical respect it receives from tackling existential issues on personal and macroversal levels.