The Elder Scrolls IV: Oblivion/Funny

"Citizen 1: "Do you think what happened to Kvatch would happen here?" Citizen 2: "Without a question.""
 * Sheogorath's quest where
 * During the Thieves' Guild quest "Misdirection", all the guards will run around the Waterfront, asking about the Gray Fox. Sometimes they'll even interrogate each other... and if you're standing nearby, they will look at you and simultaneously ask you the same question. Even better when they have the same voice.
 * "Rat Ragu with Powdered Deer Penis!"
 * In Sanguine's shrine quest, he tells you to cast a spell called "Stark Reality" on the Countess of Leyawiin and her company at her dinner party. The spell strips anyone in its range of all of their equipment, but he neglects to mention that the spell also affects the caster (you are completely stripped of all your items when you use it). Using it is also considered assault because it has a "Drain Health 1" effect, so the guards will immediately try to arrest you. So if you don't want to go to prison, (since the spell also removes all your gold so you can't pay the fine) you're forced to run out of the city butt naked with a bunch of angry guards chasing after you.
 * The stupid random conversation system in Oblivion can result in a lot of hilarity when certain lines are combined.

"Mage: "Noble scholar, may I have a moment of your time? Its rather urgent." Scholar: "Good day.""
 * Or:

"SHEOGORATH: A dangerous choice. I like it!"
 * Sheogorath's response if you choose to replace Syl:

"Protagonist: Is it the first offense? Falanu: Let's assume... no. Protagonist: Then it's at least 500 gold. Falanu: That's nothing compared to Morrowind, thanks!"
 * Let's not beat around the bush here, Sheogorath averages a brilliant and usually hilarious line every two minutes or so.
 * During a certain Mages' Guild quest (Liberation or Apprehension), you meet a Wood Elf named Fithragaer inside an Ayleid ruin (Nenyond Twyll). After a little chat, he eagerly runs deeper into the ruins to beat up some necromancers... and he runs STRAIGHT INTO A CEILING SPIKE TRAP AND GETS KILLED.
 * To top that there's a glitch that will cause the spike trap to keep activating as long as Fithragaer's corpse is on it. Meaning that the trap will continuously pummel him into the ceiling!
 * In Skingrad, ask Falanu Hlaalu about the city. She'll ask you if you know what the fine for  is, and she'll be very happy if you give her the answer.


 * Ask Owyn about rumors. "I heard a rumor that you're an idiot. There any truth to that?"
 * Sheogorath, at one point during the Shivering Isles expansion, says, "I'm so happy I could just tear out your intestines and strangle you with them!"
 * Aldos Othran's Cliff Racer song.
 * "You have pleased the Mad God! I, for one, would still like to eat your eyes!"
 * The Adoring Fan. Dive Rock. That is all.
 * When you ask Modryn to be second-in-command, he says "I was just getting used to being retired. You can see how good my painting is getting." In the back of his house you can see an example of one of his paintings.
 * If Game Mods count, there's one mod that overhauls the way beggars work (so they can pickpocket you if you stand to close to them, you can contract diseases from them, et cetera) in addition to adding several new ones around the game. One of them, in Skingrad, is a skooma addict and has his own lines. The only thing he'll ever say, no matter what you ask him, is "SKOOMA!". One of your dialogue options? "Aagh, get away from me, you freak!". To which he replies "SKOOMA!".
 * There's a woman in the Shivering Isles who's addicted to skooma, which she asks you for every time you talk to her. If you give her some, she shouts "Skooma! SKOOMA!" Of course, YMMV.