Stepford Smiler Seta Soujirou, while fighting Rurouni Kenshin, was already starting to suffer from a Villainous Breakdown, is muttering that Kenshin wasn't around to protect Soujirou when it mattered. Kenshin destroys what's left of Soujirou's cool with one question: "Is it too late to start over?"
Revenge obsessed villain Enishi flips out when Kenshin asks if his dead sister is smiling for him.
Mahou Sensei Negima! plays this for humor, with Yue reducing Kotaro to a shivering heap with a series of these types of questions. ("What is love?" "What is the meaning of your existance?", etc.)
There is a more recent example played by Negi, which should amount to a Crowning Moment of Awesome, on Smug Snake Kurt Goedel as he calls him out on the real nature of the Magic World (with state secret level information, that Negi could not possibly normally know about (thing is, he had his personal information source on this specific issue in the person of Chao...)), and on why he only wants to save the people of his country and not the whole world (meaning he is virtually leaving 17 out of 18 of the Magic World to die). This is particularly satisfying as finally his composed attitude breaks down, when even a Curb-Stomp Battle brought about by Negi's Superpowered Evil Side didn't faze him.
Negi himself was recently asked an earth-shattering one that he can't bring himself to openly answer: "Which girl do you like the most?"
In Fullmetal Alchemist, Barry the Chopper upon defeat mind rapes Al by asking him how he knows he is even real. This leads Al to question whether he ever existed and if his memories weren't implanted by Ed. Naturally, this turns Al against Ed for a few episodes. Later in the series, the final words of Homunculi also pierce their armor.
An even better example comes later in the series, when Nia is taken over by her Anti-Spiral programming, and insists she no longer has any emotional ties to her past life. Simon responds to this by asking why she's still wearing her engagement ring.
In Naruto, after the revelation that Danzo might have manipulated Mifune into making him head of the alliance, Gaara notes that if people cannot trust each other, there is no future for the world. While the Tsuchikage mocks his ideals, Gaara asks the other Kages "When did all of you throw yourselves away?" and in so doing, causes the Tsuchikage to remember "how (he) was before (he) became a stubborn old man" and veto a potential plan to eliminate the eight- and nine-tailed beast hosts.
Wufei: How many people do you think have died for you?!
Treize: Do you really want to know? As of yesterday 99,822 people.
Treize: Lady, how many fatalities today?
Lady Une: We have confirmation of 82 White Fang soldiers and 105 of our own.
Treize: I see. Give me their names later today.
X has a Tearjerker along the lines of a villainous Armor Piercing Question. The question, asked of a 14 year old schoolgirl named Yuzuriha Nekoi. "Why is it wrong to kill humans?" Which, in intent, amounts to something like "Why are you guys the Good Guys and we (the Well-Intentioned Extremists) the Bad guys?" The Tearjerker? Her pet spirit wolf, who has been with her essentially since birth, springs forward to fight for her. And is immediately killed, causing said Genki Girl to go through a less over-dramatic version of a Heroic BSOD.
Yuzuriha finds an answer to that question, by the way, which is "Because someone will always grieve for your victim".
Kaze no Stigma: "So what are you doing with your powers now? I wouldn't call this protection, would you? And you're not defending anyone by trying to avenge the past. Tell me, who are you protecting now, Kazuma?"
Death Note: After 25 episodes trying to get rid of each other, L knows he's lost and Kira (Light) will kill him at any moment. Up until this point they never openly admitted their mutual antagonism (at least Light didn't) until L asks him "Tell me, Light, from the moment you were born, has there ever been a point where you've actually told the truth?" In the anime the sound of the rain stops and the focus is on Light's shocked face to show how earth-shattering the question is.
It should be explained that L and Light both understood that they were opponents in a game that would end in the other's execution in the name of justice, so they never spoke aloud about their competition for fear of the other gaining the upper hand. It's extremely significant that the outrageously over-the-top cautious L puts the game on hold to ask Light directly if he really is just that horrible of a person.
During the Final Battle, Kagome questions Naraku's motives, observing that he couldn't have manipulated people's hearts so successfully if he didn't understand the human heart. She realises that the reason he still hadn't absorbed the Shikon no Tama was because the transformation into a youkai would destroy his human heart (and thus his power to manipulate the hearts of others). She shatters his composure by asking him if the Shikon no Tama failed to grant his real wish. Naraku's true wish was for Kikyo's heart, which he could never have, so he settled for his second-best wish which just happened to be the same wish the Shikon no Tama itself had.
Earlier, Naraku's own subordinate asked him what he was going to wish for now the Shikon no Tama was completed. This makes Naraku understand for the first time that things are coming to an end and that if he cannot have his true wish, he needs to settle for the one wish he wants that can come true, and that is a wish that will not come true immediately. He didn't want the thrill of having a Worthy Opponent to ever end and knows the Shikon no Tama will grant this desire because it overlaps with the jewel's own desire to survive. The jewel's original souls are almost burned out and need to be replaced. Naraku is willing to replace the evil youkai if the jewel uses Kagome to replace the original miko. Naraku gets eternal battle with a Worthy Opponent and has Kiyou's reincarnation with him forever while the renewed jewel has its survival ensured.
In Medaka Box, Ajimu asks Zenkichi just how he plans to "defeat" Medaka. In other words, what exactly does Zenkichi want from his upcoming battle with Medaka? After some soul-searching, during which he deconstructs his own Subordinate Excuse, he finally has his epiphany: "Ah, I see. I want to go out with Medaka-chan."
In episode 7 of Hell Girl, when budding actress Ayaka is banished to Hell, she says that through acting, she can become anybody. Hone Onna promptly asks her: "So...is there a real you in there?"
The Big Bad of Ghost in the Shell: Stand Alone Complex 2nd Gig,KazundoGhoda, delivers one to all of Section 9 after he blatantly uses them to transport a case of stolen plutonium out of a dangerous area, he intentionally opens the case to reveal it was empty, and informs that the real case of plutonium was safely recovered by the military. Batou protests how the jerk just used Section 9 as a decoy, leading to this as his response, making them realize even Section 9 could easily be wiped out in a fight if the enemy has numbers on their side.
Tea: What do you have? What do you have at the end of the day? Tell me? TELL ME!
Although Kaiba tries to play it off cool ("I have everything I need."), he is visibly shaken.
In an episode of Yu-Gi-Oh! ZEXAL, Yuma duels a guy who is a member of a famous soccer family. The guy rants that he hates soccer and has become a duelist to get out of his brothers' shadows and prove himself better than them. Yuma shakes him up by asking, "Then why are you using a soccer deck?"
In Girls Und Panzer, Miho tries giving her mother one in the prequel manga, Little Army, regarding whether Maho needed to shoot an enemy flag tank that went to rescue her teammates, but it fails; her mother coldly brushes off the question as "foolish", and essentially says yes, but the fact that she asked it causes Maho to realize how desperate Miho is, and apologize for her aloof behavior. Miho gives a more successful one to Anchovy in the main series manga when Anchovy approaches her after losing to her.
Anchovy: There's no meaning to doing Panzerkraft if you don't strive for victory!
Miho: So, is there no meaning to all the efforts you and your comrades gave?
In Season 2 of Gundam 00 Setsuna gives one to Saji to calling him on not knowing that War Is Hell and being selfish. Saji's response is to stumble over his words as it sinks in.
Setsuna: "So as long as you're the only one living in peace, you're happy?"
Saji: (pained expression) "T..That's not what I meant."
In Bakuman。, Azuma, an older and out of work mangaka who once worked as the main character's uncle's assistant, ends up collaborating with Nanamine to re-establish himself. Azuma says that he couldn't think of anything better on his own, and Hattori says he understands the feeling, but then asks him "Do you think Taro Kawaguchi would be happy about this?" That question resonates most with Azuma out of everything he and Hattori had discussed, and ultimately, he manages to, with Hattori's help, establish a series that gets serialized in Jump and thwarts Nanamine's plan.
In Muhyo And Roji, after Roji is put on leave as Muhyo's assistant in order to think about what he can do, he starts staying with Judge Imai. Roji then begins offering to do chores for Imai, who angrily responds with "Is that what you want to do? ERRANDS?!" before telling him about how her subordinate Fujiwara was incompetent and cowardly, but worked his fingers to the bone. After that question and the follow-up doesn't quite sink in, Imai replies with "You don't want to know anything, do you?" which results in Roji taking the first steps toward finding out what he can do to improve.
In Saiyuki, the villain Kami-sama, who has stolen Genjo's sutra, claims that he was trained by a Sanzo priest and inherited the title from him. However, Genjo has a question for him: "If you really inherited the title, where the hell's your Sutra?" He goes on to point out that Kami-sama went out of his way to steal a Sutra from Genjo because he didn't have one of his own, and that his master may have taught him everything he knows, but he still never gave him the title of Sanzo. At this, Kami-sama finally snaps.
Alien granter-of-wishers Kyuubey gets an Armor-Piercing Line in Episode 6 of Puella Magi Madoka Magica. The line sounds fairly innocuous if you don't know the show, but it triggers several huge reveals that lead to many of the events in the latter half of the series.
Kyuubey: That wasn't good, Madoka...no matter how mad you are, you shouldn't throw your own friend away like that.
Kyubey, in response to Sayaka's anger over the above coming out, asks two questions of her. Sayaka's fall into despair is, among other things, coming to regret her becoming a Magical Girl, .
Sayaka: Why... why do we have to go through all this...
Kyubey: You had a wish you wanted granted even if it meant being fated to live a life of battle from then on, right? And that wish has certainly come true, hasn't it?
Superman: Red Son: "Why don't you put the whole world in a bottle, Superman?"Lex Luthor sends this in a letter rather than saying it. This question brings Superman to his knees.
The whole story actually builds to this one question. It is asked as Superman, who has been able to spread his dictatorship peacefully up to this point, is finally forced to use force to take over the rest of the world. It both references his (only) failure to re-enlarge a shrunken city and compares him to fellow alien conqueror Brainiac, who shrunk the aforementioned city in the first place, and who is being used as a tool by Superman at this point to maintain his dictatorship (which actually makes "putting the whole world in a bottle" a valid option for him).
House of M leadup ("What would you have me do?"). The Avengers are coming to kill the Scarlet Witch because she is destroying reality. Quicksilver confronts Magneto about it. Magneto asks the question. Quicksilver repeats the information. Magneto repeats the question.
In Serenity Rose, this is done three times in as many pages when we're shown excerpts from the documentary "American Gothic"; The creator of a trashy, unoriginal comic is asked how many goth comics he's actually read after he continually derides them, the bassist of a goth/punk band is asked whether every fashion statement has to be political after she repeatedly rails against teenage girls who only subscribe to the lifestyle superficially, and nihilistic maniac superstar Rivet Hed is simply told straight up that "In the 16th century, they burned people like you at the stake."
If not parodied, then certainly not taken seriously in Green Lantern. Hal Jordan has gotten a blue (hope-powered) ring against his will, and it won't unlock its full powers for him until he answers a question: "What do you hope for?" Since he can't make the ring leave him until he unlocks its full powers, and until then it just sits on his hand asking again and again, and he gives a series of insincere answers like "World peace," Hal eventually snaps, "I hope you stop asking me that question!" The ring accepts this as a sincere answer.
The Chick Tracts are notorious for having uber-religious protagonists deliver what they think are armor-piercing questions to Straw Evolutionists. The questions may be armor-piercing in-universe, but they never stand up to scientific scrutiny.
In "Sin City", Ray, a gay minister, quotes Bible verses to argue, among other things, Sodom was not destroyed for the sin of homosexuality to Malcolm, a fundamentalist who was beaten up by the police and charged with a hate crime for an anti-homosexuality demonstration at a gay pride parade. After a lengthy exposition regarding Chick's views on homosexuality, Bob delivers two questions in rapid succession to Ray.
Bob: Malcolm lovingly tried to warn homosexuals of God's judgment. So who committed the hate crime? Malcolm, or the guys who almost beat him to death? Tell me, Ray, of all the sins, lying, adultery, stealing etc., can you think of any other sin where God Himself wiped out entire cities to remove that sin?
Ray: No... No I can't!
A fairly common one is the Christian witnessing to a non-Christian asking the other whether he or she has done anything wrong at all. It's The Law has one such exchange between Bob and his nephew's teacher.
Bob: So now you've admitted you're a lying thief. The 10 Commandments show us we are ALL guilty before God- We are ALL sinners.
It was only asked of Spider-Man once, but the question was so profound that it didn't need to be repeated: "Did the radiation enable the spider (who bit you) to give you powers, or was the spider trying to give you those powers before it died of the radiation? What came first, the powers or the radiation?" The question hit Spidey as hard as any foe ever did, and he had no idea what the answer was.
And then there that other question: But as you go, given this last chance, remember one thing... The man died, the Spider was reborn. I... was reborn. So the question is... are you you? Or are you me? Are you the man who dreamed of being a spider? Or the spider who dreamed of being a man? Are you the one or are you the other?
Worth noting that he decided that it didn't matter...
In the Extremis run, Tony Stark manages to double this up with a sort-of Shut Up, Hannibal! when he delivers this to John Pillinger, an anti-war activist/documentarist who is interviewing him in regard to the weapons Tony designed for the military over a decade ago, when Tony was nineteen.*
Albeit an area denial weapon that sprays BB-sized bombs everywhere, each with the explosive power of three sticks of dynamite. Eighteen percent of them had timer failures, so people in those areas are still finding the damned things and getting blown to salsa dip. Well, it was his first military project... at nineteen...
Over the course of the interview, Pillinger is clearly determined to make Tony out to be as unsympathetic as possible to the point of insinuating that he is Not So Different from any current arms dealer; he interrupts Tony at every turn, gives Tony no chance to expand on his answers, and more or less dismisses incredibly significant medical breakthroughs as meaningless just because they aren't available in third-world countries.*
Also, he asks (paraphrasing here) if a kid in Iraq with no arms would be impressed by the Iron Man armor, completely ignoring the fact that Iron Man has repeatedly saved/played a large hand in saving the planet and routinely helps keep New York from being turned into rubble.
He also brushes aside the fact that Tony hasn't designed weaponry for the military in over ten years, and has in fact put his efforts and resources into venues that could improve the world. The real kicker comes when Tony, rather than attempt to make excuses for the damage the weapons he once designed have done, flat-out admits that he knows that no matter what he does, he will always have blood on his hands — and Pillinger reacts as if Tony has given some long, rambling explanation to excuse himself from responsibility. Tony ends his statement by saying, with obvious sincerity, that he's trying to be a part of making the world a better place regardless. Pillinger responds with a caustic "...I see." However, at the end of the session, Pillinger asks Tony why he agreed to the interview. Tony responds beautifully with an Armor-Piercing Question of his own.
Tony: I wanted to meet you. You've been making your investigative films for what, twenty years now? I wanted to ask: Have you changed anything? You've been uncovering disturbing things all over the world for twenty years now. Have you changed anything? You've worked very hard. Most people have no idea of the kind of work you've done. Intellectuals, critics, and activists follow your films closely, but culturally you're almost invisible, Mr. Pillinger. Have you changed anything?
To his credit, Pillinger doesn't even hesitate in responding.
Pillinger: I don't know.
Tony: Me neither.
The two menches shake hands amicably before parting.
Butch gives an epic one to both Anita and Gila at the end of the Confidential arc in Spy Boy.
In Birds Of Prey, the Question once managed to get Huntress (whose Berserk Button is crooked cops) to back down by boiling the entire sorry socioeconomic underpinning of Gotham City's hellholishness down to one simple question: "Do you know how much an honest cop makes in Gotham before taxes?"
In Doonesbury a soldier asks her friend what she'll say if she's asked "Was it worth it?", to which her friend says that joining the army was great*
sexual assault and dismissive attitude of her commander aside
for her. Her friend responds that they'll be asking if the war was worth it; her friend's response is "what do you think I'm avoiding answering?"
In The Sandman, Morpheus asks one of these. Archangel Lucifer, having surrounded Morpheus with the Legions of Hell and intending to trap him, claims that Morpheus is powerless as dreams have no power in Hell. Morpheus asks him, and the assembled demons, what use there would be for Hell if those in it could not dream of Heaven. The demons disperse and Lucifer is forced to let him go.
In Blackest Night, Nekron asks a captive Guardian why his people chose to defend the cosmos in the first place. The Guardian's response: "I don't remember." It's a sign of just how far the Guardians of Oa have fallen and a hint of how much worse they are going to become.
In Hel On Earth, after Superman is done gathering information from Lex Luthor, Lex Luthor gives him something to think about.
Lex Luthor: Why can H'el do much more than you? Is he more powerful than you... or have you just failed to make yourself as powerful as he? And if that is the case... what are you so afraid of Superman?
Escape from under the Hokage's hat has Kakashi on the receiving end of a couple for (in canon mind you) teaching Sasuke way more than Naruto and Sakura. To elaborate he only taught Naruto and Sakura ONE skill yet focused more on Sasuke.
Sakura : (Kakashi indiectly calls her weak in front of Jiraiya and Team 8 while she points out he abandoned training her) "What part of Those who abandon their allies are worse than trash do you believe?"
Jiraiya (On why he didn't teach Naruto ANYTHING) : "You didn't want to teach him (Naruto) anything that would've pissed off the Uchiha right?"
"Then let me ask you a question Kakashi-san. Is it true that the only true technique that you taught Naruto and Sakura before the Chunin Exams was the ability to walk up trees with chakra? Or how about the rumor that Uchiha Sasuke started suddenly pulling new fire jutsu out of nowhere during that same period? The thing you should be asking yourself is not Where did I go wrong with the Uchiha?. It's What would have happened if I made the others stronger?. Would Sakura have been able to stop Sasuke from leaving in the first place? Would Naruto have been nearly killed twice because he couldn't go any farther on his own? It's because you're asking the wrong questions that you're not finding the right answers."
Used by a therapist in the Ranma Fanfic Decode Chapter 11. Note unlike most examples this was done to help him.
"Do you have anything that's unrelated to martial arts that you're sure about? Just with life in general?"
In My Little Denarians, Fluttershy does this to Fallen-possessed Rarity. She asks Demon-Rarity, despite her lightning powers, mind-control abilities, and a freaking lightsaber:
Fluttershy: Why haven't you killed me yet?
Ryo from the Tamers Forever Series often uses friendly versions of these against Rika to covertly tease her about her relationship with Takato
Chaos is on the receiving end of several from Takato and Ruki
In With Strings Attached, the Hunter confesses to Paul that he's envious of the friendship between the four, and that his life, while rewarding and exciting, has left him without anyone he could trust with his soul. Paul then asks him a series of probing questions about whether he actually likes his life, ending with, “Don't you think if you were really keen on your life, four days with us wouldn't've made any difference?”
L: But before you became a God, you were just a man. As a man, you have died, and now you are a God. So I am asking Light-kun what it is like to die.
In the Katawa Shoujo fanfic Weekend at Hisao's, Hisao is having a phone conversation with Misha about a fight that he had had with Shizune earlier that day because he refused to go over to a party that his friends at his old school were planning that night, because Iwanako, the girl he confessed to, was going to be there. He explains that the reason he did not want to go was because he could not stand to be pitied by his old friends like he was after he had his heart attack, and he recalled them looking at him and Shizune with what seemed like pity. Misha responds with two of these questions:
Misha: Why didn't you tell any of your friends that you were going to be in town?
Gaara: Existence can only be proven by being stronger and killing those stronger, their deaths make me stronger.
Harry: Once they're all dead, what will you do then?
Gaara: Stop... stop screwing around with my head!
Harry: I'm not. It's a simple question. Once you're the strongest, what will you do then? How can you prove your existence if all those who had once been 'strong' are dead?
A Growing Affection: Nagato admits to Naruto that the main reason he is helping Gouki is because if Gouki succeeds in becoming ruler of the continent, he will have right and authority to forgive Nagato for failing to protect Yahiko and the original Akatsuki. Naruto, who knows (thanks to Ino's Mand Transfer and Kakashi's deductive reasoning) that each Path of Pein contains part of the mind and soul of the original person, asks "What about Yahiko? Does he forgive you? Does he have the right to forgive you?"
Death Note Equestria: When Twilight sets up Sunny Days to die as part of a plot to clear her own name, Byuk asks Twilight what she did to deserve to die. Twilight's weak excuse causes her to face the fact that she's been killing innocents, as opposed to her original plan of just killing criminals, and she has a miniature breakdown before composing herself.
On their very first adventure together, Holmes is on his Hiatus, and the Doctor has just lost Rose Tyler and spent Christmas with Donna Noble. And when the Time War enters the equation, Holmes tries to get the Doctor to open up: “It is not my wish to distress you, my dear sir, and I am all too aware that there is a great deal more to this than you would wish to divulge. But I ask you, Doctor: how I am to aid you effectively if you will not confide in me?”
“What did he tell you, I wonder, of the Last Great Time War? Did he tell you of the battles he waged? ... He told you none of this, did he?"
“Ah, so is this truly about me, or is it about yourself, Holmes — as usual? Are we truly speaking of your concern for my wellbeing, or your own selfishness?
Holmes later quotes this question of Moriarty's: "Of the two of us, which is truly the more reprehensible: the man who never had neither friends nor a heart, or the man who had both and sold both away in a childish desire to avoid emotional pain?"
Word Of God states that he did this so as to link as to why Ben is so cold in the Time Skip episode in the series.
In Don't Blink, the Doctor is wrongly suspected of murdering a man at one point. He briefly freezes up during an interrogation by a police officer when the officer asks him out of the blue "Are you a killer?", as the question causes him to flash back to his actions during the Time War.
In the Total Drama story, Legacy, Courtney rants about her unfair elimination and thoughtlessly says that she should have been kept on instead of the recently murdered Gwen. Noah shuts her up by saying, "She would be here. Alive. And you?"
HogyokuExMachina: Ichigo has traveled back in time (to the end of the Soul Society Arc) from near the end of the Deicide Arc. Ishida is more then a little disturbed by Future/Ichigo's vehement desire to kill Aizen, wondering what happened to turn him:
"Kurosaki. When did this become some kind of grudge match between you two?!
In the final arc of Yu-Gi-Oh! Forever, after main character Yugo (Yugi's son) is angrily called out by Serenity and Yugi for making a two-edgeddeal with theBig Bad that will result in either his own death or the deaths of thousands of innocent civilians, all for the sake of trying to rescue Kaiba's mind-controlled son from said Big Bad, in despair Yugo asks his father one question:
Would you just stand by and do nothing while the bad guys took one of your closest friends away from you?
Fridge Brilliance also kicks in to make the question more potent: in canon, Yugi refused to do that very same thing when Marik mind-controlled his friends.
Kakashi: "You broke the deal! You were supposed to have him for 3 years and then I would take over!"
Jiraiya: "That's because you didn't hold up your end."
Jiraiya: "I left Naruto to you so you could build up his basics but you were too busy giving the Uchiha prick everything he wanted instead of helping the rest of Team 7."
Kakashi: "B..B..But! You're pushing him too hard in his development!"
Jiraiya: "Bullshit. The brat burned through everything I planned to teach so I had to do more. The Akatsuki is after him! Would you prefer I keep him weak so you can have you're desire to train him?"
Kakashi: "... (solemn) Still I wanted to teach him about his elemental affinity. "
Jiraiya: "Well too bad. You had you're chance and you pissed it away. Oh and another thing, why did you want to train him?"
Kakashi: "He's sensei's son."
Jiraiya: (scowls) "That's your problem! You see him as something other than who he is! You see the Yondaime's (4th's) son, the villagers see him as a demon! I see him as a cocky if somewhat determined and loyal blonde! Seriously, if he wasn't Minato's son would you even be training him?"
Mariko, opposing the rest of the SUEs' plan to reshape the world, tries this, but The Usurper responds with his own Armor-Piercing Questions to argue that she depends on her powers as much as the rest of the SUEs do.
Mariko: "But what makes you think that you're much better than they are to make that decision? And if they make mistakes, shouldn't they at least be their mistakes, and shouldn't they earn the negative and positive consequences of their actions?"
The Usurper: "Have you ever considered, Mariko, how much you have earned yourself? What if everything you ever had- your beauty, your grades, your maturity, your popularity and everything else- were given to you by someone else, for the sake of using you to enter another world and sway it to that person's will?"
Mariko: "Th-that's impossible. After Mother and Father died, life was often difficult, even with the wealth they left behind. I had to try hard to get by after that, and if I have many things, it's because I earned them!"
The Usurper: "Tell me, Mariko, can you recall a time when a person disliked or disagreed with you?"
She does this more successfully, albeit with the help of her powers, once the SUEs set out.
Mariko: "The question we should be asking ourselves, more than how we plan to go about doing this, is should we be trying this?"
Shizune: "What do you mean, Suou-san?"
Mariko: "In order to win, we must potentially sacrifice 10 more innocent victims, while potentially giving up our own lives, as well as the lives of those we cherish the most. And for what? Do our goals mean so much to us that we'd risk everything and cause harm to others for them?"
In the main story, Yukino asks one of Shizuru, when proposing that the rest of the student council be informed about what is going on. She says that although they may not have powers, their help may prove necessary. Yukino asks this question that causes Shizuru to reflect on what she did for Natsuki before she realized she was also a Hime, and then goes on to say that Haruka's determination may be what they need to face the SUEs.
Yukino: And, what would you do if, for example, Kuga-san were a Hime and you were not?"
Subverted in Good Will Hunting: "It's not your fault." Not quite a question, but repeating it a dozen times does bring the main character to his knees.
Also played straight a little earlier in the movie, when the simple question "What do you want?" cuts Will off in the middle of a speech and causes him to just stare blankly at his therapist. The therapist notes that Will can spin bullshit stories and justifications for anything... but he can't answer the simple question.
Hanna: We couldn't keep everyone. There wasn't room.
Judge: No, but what I'm saying — let me rephrase — to make room, you were picking women out and saying "You you and you have to be sent back to be killed."
Hanna: Well, what would you have done?
A Few Good Men: After the JAG lawyer, Kaffee, insinuates that Col. Jessup had been disobeyed by his soldiers - something which Jessup would be absolutely loath to say, even if it was a lie to cover his own ass - he asks:
Galloway: So let me ask, if we ultimately conclude that our national security is best served by denying you further asylum on our planet, will you leave peacefully?
Optimus Prime: Freedom is your right. If you make that request, we will honor it. But before your president decides, please ask him this: What if we leave and you're wrong?
Lennox (to Galloway): That's a good question.
In Transformers: Dark of the Moon,] Carly asks Megatron about if he'll really rule the world, going as far as saying he'll be "Sentinel Prime's bitch". He considers killing her, but realizes she's right.
The Matrix has the Dare to Be Badass variety. "Do you think my being faster or stronger has anything to do with my muscles in this place? [Neo shakes his head no, while breathing heavily] You think that's air you're breathing now?" Asked by The Mentor, of course.
Smith: Why, Mr. Anderson, why? Why, why do you do it? Why, why get up? Why keep fighting? Do you believe you're fighting for something, for more than your survival? Can you tell me what it is, do you even know? Is it freedom or truth, perhaps peace - could it be for love? Illusions, Mr. Anderson, vagaries of perception. Temporary constructs of a feeble human intellect trying desperately to justify an existence that is without meaning or purpose. And all of them as artificial as the Matrix itself. Although, only a human mind could invent something as insipid as love. You must be able to see it, Mr. Anderson, you must know it by now! You can't win, it's pointless to keep fighting! Why, Mr. Anderson, why, why do you persist?
One of filmdom's most famous examples comes from Marathon Man: "Is it safe?" Three words which comprise Sir Laurence Olivier's first eight lines of dialogue. It's also an interesting subversion of the trope, since Levy dearly wishes he could answer Szell's question, but he genuinely does not know the answer. Not that Szell believes him. Ouch.
Mustapha in Austin Powers was especially vulnerable to the trope. He'd have to answer any question asked three times. Also, at the end of the second movie, Felicity Shagwell asks Fat Bastard "Are you happy?"
Titanic: After Jack saves Rose, she meets him the next day for a formal thank-you. She blames it on the stress she felt over her upcoming wedding, when Jack stops her in her tracks by asking "Do you love him?" She finds five different ways to avoid the question.
Constantine ("What did she do, Angela?") Constantine tries to get Angela Dodson to figure out where her twin sister left a message.
"What did she do, Angela? You know what she did. What did she do, Angela? You know what she did. What are you afraid of? What did she do? What did she do? What are you afraid of?!?"
In Grumpy Old Men, John and Max have been feuding for years after falling out over a woman when they were young, and a new love interest has only made things worse. However, when John has a heart attack and Max goes to see him in the hospital, the nurse asks him "Are you friend or family, sir?". A shaken Max pauses for a long time before concluding "...friend."
In Dracula 2000 Mary is losing the fight to Dracula, after discovering that he's actually Judas. Halfway through the fight Dracula snarls at her as they stare at a cross: "He won't have me," (referring to his immortality) to which she replies: "did you ever ask?" The question clearly hasn't occurred to him before, and it's enough to give her the upper hand.
Green Goblin:If there's one thing [people] love more than a hero, it's to see a hero fall, fail, die trying. Despite everything you've done for them, eventually they will hate you. So why bother? Spider-Man: Because it's right.
Inverted rather cleverly in the Daredevil film, in which Matt Murdoch receives an armour-piercing answer to a theoretically rhetorical question. While in the confessional, no less.
Matt: "Is justice a sin?" The priest: "Vengeance is!"
For context, the sins he's currently confessing to are as a result of going Vigilante Man on a mob boss who was being prosecuted for rape, and whom Matt feels got Off on a Technicality. This would be morally dubious enough already, as rape cases often come down to one person's word against another's, but Matt was the lawyer for the prosecution! In the circumstances his confessor actually lets him off quite lightly, but he makes a sufficient impression that Matt eventually adopts a policy of Thou Shalt Not Kill that's at least in line with accepted Church doctrine.
It should be noted that Matt's super-hearing makes him a Living Lie Detector (he can hear people's heartbeat speed up when they lie,) so he did at least know for an indisputable fact that the man was guilty. It should also be noted that it's unclear whether Matt was intending to kill the man from the start, and it could even be argued that it's a case of refusing to Save the Villain; the man had been about to kill him, and in defending himself Matt knocked him onto the railway tracks. He then taunted him about the oncoming train rather than helped him up, even though he could have done, so it's a matter of opinion whether this counts as a cold-blooded execution, or killing him accidentally and being perfectly happy about it.
It almost literally becomes an Armor Piercing Question, when Fox asks Wesley this by beating the crap out of him. Made even more explicit because when his formerly aimless, smug demeanor is broken, he finally answers the question. And when he finally answers the question we begin to see him actually master the skills he's being forced to learn and become the badass we was meant to be.
Subverted for humor in Field of Dreams. Ater all but kidnapping one of his heroes, the author Terence Mann, to take him to a baseball game, Ray asks Terence, who's in the middle of a rant about why he's all but in hiding from the world, what he wants. As one might expect from a writer, Terence has his answer ready. A recluse from all the hippies he inspired in the sixties, he snaps that he wants people to stop asking him for answers, start thinking for themselves, and give him his privacy. Ray says, somewhat nonplussed, "No, I mean...whaddaya want?" and gestures. Terence follows the gesture...and sees an impatient looking concession stand worker. "Oh. Dog and a beer."
Nuremberg has Robert Jackson considering quitting, and his wife asking him "does Herman Göring actually believe in his ideals more than you believe in yours?"
Wreck It Ralph, when Ralph realizes that Vanellope, who had been branded a criminal, was meant to be in Sugar Rush, he confronts King Candy's lackey Sour Bill and asks him this:
Ralph:"If Vanellope was never supposed to exist, why is her picture on the side of the game console?".
In the seldom-watched sequel to Arthur, Arthur, followed around by the ghost of Hobson, goes to his nemesis Susan Johnson to admit defeat and marry her so that he can get his fortune back. The doorman asks "is she a friend of yours?" Hobson comments: "It's a very perceptive question, isn't it? Cuts right to the heart of the matter."
At the end of Disclosure, Tom (Michael Douglas) and Meredith's (Demi Moore) final verbal match ends with him asking her, "Did it ever occur to you, Meredith, that maybe I set you up?" Meredith looks down at the floor, with nothing more to say.
Pulp Fiction has a nonserious example when Jules gives a speech on how a foot massage has no sexual implications whatsoever, to which Vincent replies: "Would you give a guy a foot massage?"
In Bad Day at Black Rock, Macreedy knows that something is wrong at Black Rock, and that Smith is near the heart of it.
Smith: I swear, you're beginning to make me mad.
Macreedy: All strangers do.
Smith: No they don't. Not all of 'em. Some do when they come around snooping.
Macreedy: Snooping for what?
Smith: I don't know. Outsiders coming in looking for something.
Macreedy: Looking for what?
Smith: I don't know. Somebody's always looking for something in this part of the West. To the historians, it's the "Old West." To the book writers, it's the "Wild West." To the businessman, it's the "Undeveloped West." They say we're all poor and backward and I guess we are. We don't even have enough water. But to us, this place is our West. And I wish they'd leave us alone.
Macreedy: Leave you alone to do what?
Smith: I don't know what you mean.
Macreedy: What happened to Komoko?
Coach Carter is disturbed that the system his school has expects the students to fail. He tries to inspire the players on his team to rise above the system. The principal disagrees has it out with Carter.
Principal: "Your intentions are good, Mr. Carter, but your methods are a bit extreme." (locking the gym until every player gets at least a 2.8 GPA)
Carter: "You painted an extreme picture."
Principal: "No one expects them to graduate, no one expects them to go to college. So you take away basketball. The one area of their lives where they have some success."
Three O Clock High. Jerry Mitchell (Casey Sziemasko) offends the new student, Buddy Revell (Richard Tyson), who now wants to beat Jerry up. Jerry will do anything and everything to avoid the fight, and ultimately offers Buddy $350 to leave him alone. Buddy takes it, but says to Jerry, "You're the biggest pussy I ever met in my life. You didn't even try. How's that feel?" The question makes Jerry decide to go through with the fight, even though he knows he'll probably get hurt, to prove he's no coward.
It's not actually a question, but it does fit. In the Star Wars Expanded Universe, Padme's Body Guard Crush, Captain Typho, searching for her murderer then finding him and getting utterly curbstomped, manages to stop Darth Vader cold by telling him "I know you killed Padme." He still gets killed after the pause, but he's comforted by the knowledge that he hurt the Dark Lord. Though, not knowing the actual events, he never knows why - his investigation basically went: Padme was killed with the Force, Skywalker was supposed to be bodyguarding her, Skywalker was killed shortly before her, Vader appeared after that, therefore Vader killed them both.
When Zedd is describing Seekers in Wizard's First Rule, he references this trope, saying that a truly great Seeker could bring even a king to his knees by asking a question.
Blade of Tyshalle ("What do you want?") The opening quote is about two-thirds of the way through a dressing down Tommie gives Deliann, which takes a little under a page and a half. "What do you want?" happens to be both the identifying codephrase and the central tenet of the persecuted philosophy Tommie holds. Tommie has to ask the question, with mildly different phrasing, over five times. No, Deliann, not what you feel guilty about, not what you think went wrong in the past, not what you like or wish or would settle for. What you want.
Lois McMaster Bujold's A Civil Campaign ("Why didn't you say 'no'?") Miles makes a horribly clumsy public proposal to Ekaterin, who storms out in a rage (for complicated reasons). Later, when Ekaterin is discussing the incident with her aunt, her aunt notes that running off was Ekaterin's way of avoiding the question, and that she could have said no.
Ekaterin "It wouldn't have been polite."
The Profesora "You could have said 'no thank you'."
In the third book in Jonathan Stroud's The Bartimaeus Trilogy, Kitty asks Bartimaeus a single question. "What about you and Ptolemy? The question gets to him so badly that we don't see his reaction until the next chapter, where about half of it deals with him absolutely breaking down and scaring the crap out of Kitty.
Used in The Tale Of Despereaux. The question in, well, question is "What do you want, Miggery Sow?" This comes as such a shock to Mig, who'd never been genuinely asked, that Pea only had to ask once.
A couple of examples from The Belgariad- Garion has a dream the night before his Awesome Moment of Crowning where everyone asks him "Are you ready?" until he accepts that yes, he's ready to take up his birthright.
A sort of inversion of this is that all throughout the series, he keeps asking "Why me?" His aunt finally returns the question, "Would you trust anyone else to do it right?" To which Garion is forced to reply that no; he wouldn't really, therefore burying this question forever.
Gordon Dickson'sChilde Cycle: Founding Father of the Dorsai, Cletus Grahame, has forced Melissa Khan to marry him as part of his overarching strategy as he explains exhaustively in their bedroom on their wedding night. Melissa has only one question; "Then you never loved me?" "Did I ever say I did?" Cletus responds, and leaves the room. This tells Melissa all she needs to know. He loves her. If the answer was "No", he would have come right out and SAID "No" instead of evading the question.
Catch Twenty Two has Yossarian ask the show-stopping question: "Where are the Snowdens of yesteryear?" (It's eventually revealed that Snowden had died horrifically during a bombing run, waking Yossarian up to the Crapsack World around him and causing him to realize that he really, really didn't want to die, not for anything.)
In Fahrenheit 451, Clarisse causes Guy to begin questioning his entire way of living by asking the simple question "Are you happy?" and causing him to realize that no, he isn't. He's unable to automatically smile after that as "she had run off with it and he couldn't just knock on her door and ask for it back."
In The Dresden Files book Small Favor, Michael asks the question "Where is your blasting rod?" to Harry, because Queen Mab of the Winter Court stole it without Harry noticing earlier in the book, and then put Harry's mind into a brainlock that kept him from remembering either his blasting rod or the ability to use fire magic. Harry himself never realized this had happened, and the question sends him into a brief but intense spasming fit once he realizes what had been done to his mind.
In John C. Wright's The Golden Transcedence, Diomedes cites the Silver-Gray cultivation of such questions — such as, if a philosopher tells you it's right to lie, why do you not suspect him of lying when he says it? Loading such questions into the gadfly virus proves crucial.
In the Star TrekNovel Verse, we have "Are you Whole?" for the Andorians. Supposedly asked of the mythical hero Thirishar by all-powerful Uzaveh (AKA Andorian God), the question drives the modern Andorian culture in its entirety. To be truly Whole requires both reassembling in unity the four genders derived from Thirishar (essentially, bonding with three others in an marriage quad) and gaining knowledge of the "missing piece", an elusive aspect of racial knowledge hidden to the Andorian people. See the Star Trek: Deep Space Nine Relaunch in particular.
To Kill A Mockingbird: In chapter 15, a group of men ready to lynch Tom is stopped dead by Scout when she asks one of them how his entailment (ie: an inheritance problem) is coming along. In this case, it's not specifically the question that's armor-piercing so much is that it's coming from the innocent young daughter of Tom's defense lawyer - it breaks the men out of their mob mentality and they quickly disperse in embarrassment, much to the confusion of Scout, who was only trying to make small talk.
The original Fisher King could only be healed by being asked the right question. In some tellings, this is explicitly an Armor-Piercing Question that jolts him out of his self-centeredness; in others it just has unexplained magical properties.
Attempted by Ford Prefect in The Hitchhikers Guide To The Galaxy 1, when he asks the young Vogon guard if he actually enjoys his work. Subverted because the guard is too close-minded and stupid to do more than ponder the question for a minute or two, then resume throwing the stowaways off the ship.
In Tim Powers' On Stranger Tides, a captive pirate decides he'd rather be shot than hanged, so asks one of these ("Is it true what Panda Beecher once told me about you?") of the Navy captain who's questioning him. As Panda Beecher is a criminal who pays Navy officers to smuggle goods, on the one hand, and the owner of a whorehouse catering to "exotic" tastes, on the other, the question pushes the captain's Berserk Button and a fight breaks out. Bonus points because it's an Armor Piercing Shot In The Dark: the pirate actually knows nothing against the captain, he just knows lots of Navy officers do business with Beecher.
Lampshaded (naturally) in the Discworld novels. The philosopher Ly Tin Wheedle was asked "Why are you here?" by a fellow guest at a dinner party (because Ly Tin Wheedle wasn't invited), and took three years to formulate a suitable reply.
Or Wen the Eternally Surprised who, after reaching enlightenment, told his apprentice to ask him a question, anything. His apprentice, who was quite stupid and not at all inclined to be philosophical (...or was he?), just said "Er... what [do you] want for breakfast?" "Ah, one of the difficult ones."
Also parodied with Detritus' interrogation technique, which simply consists of asking the same three questions ("Did you do it?", "Are you sure it wasn't you what done it?" and "It was you what done it, wasn't it?") over and over again for hours until he gets the right answer: "Yes! It was me! I did it! I did it! Now please tell me what it was I did!"
In Jingo, Nobby, of all people, asks some questions that puncture the anti-Klatchian rhetoric going around Ankh-Morpork.
Nobby is actually quite good at these. He'll let Colon go on a rant, seemingly agreeing with everything he's saying, then bring up one of the things Colon said earlier that pokes a great big hole in his logic.
In Good Omens, as Adam Young starts to be overtaken by his demonic heritage, his rambles about his plans to kill off all the grown-ups who've messed up the world and leave things to him and his circle of friends, which includes him divvying up the world among them. One of his friends, Pepper, asks what part of the world Adam wants, and Adam slowly starts to come back to normal as he realizes all he really wants is his hometown of Tadfield.
Perhaps the biggest Crowning Moment of Awesome in Sarum goes to Captain Wilson's wife Nellie, who upon her return to Salisbury is immediately accused by Holier Than Thou Abigail Mason of being a harlot. Not only does the Captain denounce Abigail by asking the crowd, "And who's this pasty-faced scold?", but Nellie — quickly sizing up the situation, in which Abigail and her brother-in-law have been watching her spouse Peter Mason being executed for heresy — declares the Armor-Piercing Answer, before the entire town:
"Why, 'tis Abigail Mason who's just burned her husband so she can get another."
For Artemis Fowl, it's: "Artemis... Isn't that a girl's name?" Artemis later gives his answer with a code phrase that sets the final part of an Awesome Moment plan in action.
In Angela Carter's "A Very, Very Great Lady and Her Son at Home," the lady of the title recounts her mother's advice to overcome her shyness by imagining the people who intimidate her looking ridiculous on the toilet. Her son, who has been attending to her for most of the story, proceeds to ask "And do you look pathetic on the lavatory, mother?" She promptly collapses.
In the fifth Temeraire book, Victory of Eagles, Napoleon has invaded Britain. Laurence, who technically committed treason at the end of the last book by saving the dragons of Europe from biological genocide, is given a stay of execution because the Admiralty needs someone to ferret out pockets of French troops - and he has orders to take no prisoners. It's dirty, dishonorable, and depressing, but he obeys until Tharkay arrives, sees his plans for the next attack, and plainly asks, "What are you doing?" It prompts a small breakdown from Laurence, and a frank assessment of what he is prepared to take responsibility for.
In Fated by Benedict Jacka (the first book of the Alex Verus series) a ghost asks Alex why he didn't run away and hide from more powerful wizards when he could have. Alex gives evasive answers but under repeated questioning admits he stayed to protect another person. It was a revelatory moment for Alex, as he had spent the last few years only looking out for himself.
In A Brother's Price, there is a practice in Queensland which Princess Ren hates - the small children of treasonous families are killed along with them. Her harsher and more pragmatic sister Halley reminds her that no relatives will take a traitor child, and if they do, well...
"Do you really want to be remembered as another Garrosh? Another Arthas?"
In the StarCraft novel, Liberty's Crusade, a reporter confronts Colonel Duke with a Fridge Logic question that probably works on many players - if the Protoss just appeared and started attacking with no warning or communication, how do we know their name?
"Where did we get the name 'Protoss' Colonel? Is that ours, or theirs? And if it's their name for themselves, how come we know it?"
In the Warcraft short story Of Blood And Honor, Eitrigg tells Tirion that the orcs were an honorable people who were corrupted by the warlocks. Tirion asks why the orcs would go along with the atrocities of the Old Horde if they were honorable. Eitrigg responds with the following question, and later points out that Tirion, who is a wealthy noble in addition to a paladin, has never had to sacrifice anything to do the right thing.
Eitrigg: Have you ever stood against the will of an entire nation, human? Have you ever questioned an order, knowing that to disobey meant immediate death?
In Stanley Ellin's short story “The Question,” the narrator is what he refers to as an “electrocutioner” – the man who rigs up the electric chair and throws the switch on condemned prisoners. It's a secretive job (virtually no one knows the narrator does what he does, including his son), but he's proud that he performs it well. He spends the story telling the reader of how he attempted to persuade his son to follow in his footsteps, citing society's need for the death penalty, comparing rapists and murderers to rabid dogs, and justifying his position as “electrocutioner” by saying that someone must take the responsibility for doing a job no one else wants. His son is shocked and utterly refuses to do it, and reacts with horror when his father says, “It's just a job.” The son asks, “Just a job? But you enjoy it, don't you?” As the narrator searches his soul, he reflects on all the men he's watched die gruesomely in his electric chair, and ends the story with the question, “My God, how could anyone not enjoy it?”
In one of the most emotional episodes of Scrubs, Dr. Cox is headed to his son's birthday party and is talking to his best friend, Ben. In the middle of the conversation, the camera switches so that Cox's face is in the foreground, and J.D. walks up to him and asks him what he's talking about. When Cox gives him the expected answer (the topic of the conversation), J.D. waits a Beat and asks "Where do you think we are?" The camera then switches back to where Ben was, except he is no longer there. They were headed to Ben's funeral the entire time.
In "My Fifteen Seconds", Jill Tracy is back at the hospital for unexplained poisoning. Every time Cox and J.D. talk with her, she behaves in her typical over-the-top and frivolous way. It's only later that the two doctors understand she had tried to kill herself. They rush back to the hospital and the question "How have things been going recently?" finally prompts her to tell the truth.
Happened during Season 5 when J.D. saw a dead Jill Tracy wheeled in to the hospital and her mom asks : "Could someone have done anything?". This hits J.D. hard due to him having seen signs that Jill was a Stepford Smiler with suicidal tendencies but kept avoiding her because she's a Motor Mouth. He answers with no but thinks "Unless you mean me."
Used very emotionally in the season three finale of Bones, Brennan to Gormogon's apprentice.
Not quite a question so much as a series of logical statements, as Brennan explains to Booth as he keeps asking Zack to give up the Gormogon without getting a response, "Zack responds to logic." Brennan proceeds to give a series of arguments that seem to justify Zack and the Gormogon's motives, and then delivers the armor-piercing line: "Yet you risked it all so you wouldn't hurt Hodgins."
"Who are you?" by the Vorlons, "What do you want?" by the Shadows; both of them are asked until the subject stops giving superficial answers and starts revealing things about themselves. J Michael Straczynski has a degree in psychology and cited Synanon as an inspiration.
In the fourth season, Sheridan and Delenn point out that the Shadows and Vorlons don't have answers to their own questions anymore. This is part of what convinces them to leave the galaxy once and for all.
Later, more get added. Lorien asks "Why are you here?", and the Spin-Off series Crusade adds "Who do you serve, and who do you trust?" for the humans, and "Where are you going?" for the Technomages.
In Dalek, as the titular creature is about to kill Henry van Statten:
Rose: You don't have to do this anymore. There must be something else - not just killing. What else is there? What do you want? Dalek: (Silence. Turns back to van Statten, and then back to Rose) I want... freedom.
Rose gets another one when the Ninth Doctor, filled with rage, comes running in to shoot the Dalek. Rose's question stops the enraged Gallifreyan in his tracks.
Rose: It couldn't kill Van Statten, it couldn't kill me. It's changing. What about you, Doctor? What the hell are you changing into?
Amy gets one aimed at her by "The Dream Lord" aka the Doctor's Enemy Within during Amy's Choice. He mocks her belief that the Doctor trusts her, and when she stands up to him he simply asks "So what's his name?"
Amy also gets an armor piercing statement from the Dream Lord. It's effective nonetheless.
Dream Lord: Poor Amy. He always leaves you, doesn't he? Alone in the dark. Never apologises. Amy: He doesn't have to. Dream Lord: That's good. Because he never will.
The Dream Lord gets a hefty bag of armor piercing questions to throw at the Doctor:
In series 4, Davros asks the Doctor something along the lines of "How many people have died for you, Doctor?" The answer is: a lot. As we are told, via a brief flashblack to all their faces from just the past three out of 45 years alone.
The Doctor's question to all of Britain about one Harriet Jones, Prime Minister. "Don't you think she looks tired?"
The classic series also presents a, well, classic example in The Pirate Planet, when the Fourth Doctor is confronted with a room filled with entire planets compressed into football-sized spheres and held in place by technobabble. The Doctor has asked the question lightly several times throughout the serial, not in an attempt to hurt the Captain, but to get him to drop his "loud but harmless bully" facade and admit that he has greater plans, but here is where he really hammers it home:
The Doctor: The concept is simply staggering! Pointless, but staggering! The Captain: I'm gratified that you appreciate it. The Doctor: Appreciate it? Appreciate it? You commit mass destruction and murder on a scale that's almost inconceivable, and you ask me to appreciate it?? Just because you happen to have made a brilliantly conceived toy out of the mummified remains of planets? The Captain:Devil storms, Doctor! It is not a toy! The Doctor:THEN WHAT'S IT FOR?! What are you doing? What could possibly be worth all this?!
Martha asks Professor Yana how he knows his watch is broken if he's never used it, getting him to admit he doesn't know... ...and shattering the perception filter keeping Yana from becoming the Master, the Doctor's nemesis.
And the conclusion of Series 6 now gives us the oldest question in the universe, the one the Doctor has been running away from for his entire life. "Doctor who?"
"Asylum of the Daleks" has the Doctor asking Oswin, aka Souffle Girl, "Where did you get the milk?" Sounds like a non-sequitur at first, but...
One prominent instance in Malcolm in the Middle where Commandant Spangler asks Francis "Can you name one thing wrong with your life that you don't blame on your mother?". Having blamed his mother for every problem he's ever had, regardless of how much Insane Troll Logic it took, Francis is stumped.
Pretty much the episode where the aftermath of Reese's backfired prank had resulted in a diatribe by no other than Lois. All about how Malcolm should become president by finishing High School first. Knowing how Malcolm's usual arguments end, Lois asking her own son to doubt potential of becoming a president rendered him speechless.
Several examples of this occur in The West Wing, since it's a show about career politicians with rhetorical training. Sometimes it's the White House staff trying to cut through political facades, like when Oliver Babish interviews Bartlet over his MS, and sometimes it's a reporter, such as Danny Concannon investigating the assassination of a foreign national by US intelligence.
Central to the second-season episode "Noel" is a psychologist asking Josh "How did you hurt your hand?" over and over until he tells the truth.
An amusing sequence occurs in the introduction to the re-election arc, where a potential candidate for President completely flubs the question "Why do you want to be President?". Bartlet's staff giggle incessantly over the completely unorganized and unconvincing response, until one of them asks the other "What would Bartlet say to that question?" and they realize they don't have an answer either.
Abbey Bartlet had helped her husband conceal his MS by secretly prescribing him medication. When his medical condition was revealed, his political opponents also went after Abbey for violating medical ethics. Abbey saw this as a political attack and angrily fought the charges. Donna Moss then pointed out that what she had done was a violation of medical ethics ("Mrs. Bartlet, for crying out loud, you were also a doctor when your husband said, 'Give me the drugs, and don't tell anybody,' and you said, 'Okay.'") and this made Abbey realize what she had done was wrong and she accepted her punishment.
Dr. House frequently does this to enlighten or enrage. It can be hard to tell at first why he's so persistent. He may think it relevant to a diagnosis, he may be trying to manipulate, he may simply be "trying to solve a puzzle", or all of these.
In the first part of the Season 4 finale, "House's Head", the mysterious female bus passenger repeatedly asks House "Who am I?" and "What is my necklace made of?" until House realizes the mysterious woman is a subconscious substitute for Wilson's girlfriend Amber.
In "The C-Word" from Season 8, while undergoing a massive dose of chemotherapy, Wilson hallucinates an 8-year-old deceased former patient, who asks why he died if he did nothing wrong. The question is even more devastating to him than the pain of chemo.
Heroes: Season 3, shortly after Claire is finally caught and victimized by Sylar, her biological mother Meredith (a pyrokineticist) accedes to her wishes to train her in combat inside a trailer so that she can fight villains like Sylar. Instead, Meredith repeatedly asks her "why do you want to fight bad guys?!" while superheating the air inside the trailer, causing Claire to admit the true reason behind her vigilante urges - revenge on Sylar for what he did to her (tantamount to rape.)
Sayid (to Juliette): You said earlier that if you told me everything you knew, I'd kill you. I'm going to test the validity of that statement.
Sawyer: He means "talk".
Juliette: We don't have time for this.
Sawyer: We cleared our schedules. We got all the time in the world.
Juliette: You know it's interesting... that you two are now the camp's moral police. I'm curious Sayid, how long was it before you told everyone on that beach exactly how many people you've tortured in your life? Do they know about Basra? And I'm sure the first thing you did when you got here, James, was to gather everyone in a circle and tell them about the man you shot in cold blood the night before you got on the plane. So why don't we just skip the part where you two pretend to be righteous? I'm taking that medicine back to Claire, and you're going to let me. Because if she doesn't get it, she's going to die. And the last thing either of you need right now... is more blood on your hands.
There's an even better one in Season 1. Locke leaves Boone and Shannon tied up in the jungle, allowing the monster to kill Shannon. After Boone gets free, he comes after Locke with knife, screaming accusations. As soon as he says the words "she died in my arms," Locke delivers his first APQ: "Then why is there no blood on you?" This forces Boone to realize that the whole thing was an hallucination. But then Locke drops his second APQ, asking Boone how he felt when he thought Shannon was dead. Despite his rage, Boone says "relieved," effectively concluding his arc as he sheds his emotional dependence on her.
[Jacob to Ben in the season 5 finale: "What ABOUT you?"
During season 2 of Legend of the Seeker, Richard became affected by a magic-induced rage, and to help him control it, the wizard Zedd kept asking Richard "What are you angry at?", knocking down each of Richard's answers until they got to the real answer: Richard was angry at Zedd for lying to him about heritage and bringing him into the conflict in the first place
The second-to-last episode of Season 1 of The Wire: D'Angelo Barksdale decides to quit the Game:
"Where's Wallace? Where the fuck is Wallace? Huh? Huh? String? String? Look at me! Where the fuck is Wallace?"
And a possible callback at the end of Season 4, when the System fails Randy:
"You gon' help, huh? You gonna look out for me? You gonna look out for me, Sergeant Carver? You mean it? You gonna look out for me? You promise?! You got my back, huh?!"
Cal Lightman of Lie to Me uses this all the time to get a reaction he can read off of someone.
Funnily enough, the same question actually gives her the same reaction twice. First in the future hearing it from Jesse, then again in the present from Ellison.
Emily delivers an Armour Piercing Line to Naomi in Skins during the Katie And Emily episode. Naomi is running away from their relationship (again) until three words stop her dead in her tracks - and bring her straight back for a lot of kissing against the lockers.
In the classic James Newcomer Star Trek: The Next Generation episode, "The Measure of a Man," Picard is forced to defend Data's rights when Commander Bruce Maddox claims he is not sentient and is Starfleet's property, giving Maddox the right to disassemble Data against his will to study and replicate him. Picard's defence is one giant Crowning Moment of Awesome where he questions the real implications of Maddox's work that eventually leaves Maddox shaken and silent.
Picard: A single Data, and forgive me, Commander, is a curiosity: a wonder, even. But thousands of Datas, isn't that becoming a race? And won't we be judged by how we treat that race? Now tell me, Commander, what is Data?
Maddox: I don't understand.
Picard:What is he??
Maddox: A machine!
Picard: Is he? Are you sure?
Picard: You see he's met two of your three criteria for sentience, [intelligence and self-awareness,] so what if he meets the third, consciousness, in even the smallest degree? What is he then? I don't know, do you? (to Riker, who'd been forced to argue for Maddox's side) Do you? (to the judge) Do you? Are you prepared to condemn him and all who come after him to servitude and slavery?
The Fridge Logic here is that if Picard is so careful about the slippery slope that he is pressing to err on the side of caution, warning that it could lead to servitude and slavery to deny rights to something that might possibly show the signs of the aforementioned criteria, then why exactly does he have no similar attachments to other advanced computers, like the Enterprise's (he never asks the ship if it wants to go where he wants it to go), or any other form of equipment? It was even brought up that the only reason there was such a fuss over Data was just because Data looks human(ish). These tough questions never are answered again in the series, of course (though Voyager does take a crack at it with the new Doctor).
Except of course in the episode "The Quality of Life", when the exact same issues were brought up regarding the emerging sentience of the Exocomps, and both Moriarty holodeck episodes ("Elementary, Dear Data" and "Ship in a Bottle"). Plus there was an episode where the ship DID become sentient ("Emergence"), although it was a temporary condition caused by the presence of an alien lifeform, and the crew spent most of the episode unable to communicate with it.
Picard himself is taken aback by Data's question earlier in the same episode, after he suggests to Data to agree to Maddox's procedure for the sake of Starfleet.
Data: Sir, Lt. La Forge's eyes are far superior to human biological eyes, true? Then why are not all human officers required to have their eyes replaced with cybernetic implants?
[Picard is at a loss for words and turns away]
Data: I see, it is precisely because I am not human.
Picard: [shaken] That will be all, Mr. Data.
Law & Order: Ben Stone's cross-examination of an anti-abortion activist who had tricked a woman wanting an abortion into carrying a bomb to the clinic. After the woman self-righteously declared what she had done was just, and that the victim, a former follower of hers who had become pregnant, deserved what had happened, the question came that left her speechless.
If abortion is murder, then no matter how you feel about Mary Donovan, aren't you guilty of the murder of her unborn child?
Another episode involving the killing of an abortion clinic doctor had Jack McCoy questioning the man who had arranged the murder. The defendant was trying to use justifiable homicide as a defense (that he had to protect all those unborn children by having this woman killed). McCoy pierces his armor by asking why then, if he was so sure it was right and justified and necessary, he hadn't done the deed himself instead of just arranging the murder? The man is forced to admit that he believes any killing is morally wrong and thus couldn't go through with it himself, destroying his own defense completely.
Law and Order has tons of examples of these on the witness stand.
Criminal Minds has Constantly Curious Ellie Spicer ask Tim Curry's character (a serial killer) why he kills people. Subverted when he replies that the best question would not be why he kills people, but why he doesn't kill all of them.
The Prisoner episode "The General" shows Number Six defeating a highly advanced computer by Logic Bombing it with a question which he is certain its predictive and logic circuits will not be equipped to answer: "Why?"
Prisoner: It's insoluble, for man or machine.
And in "Hammer into Anvil", after exploiting Number Two's paranoia all episode:
Two: Sent here by our masters to spy on me.
Six: ... Just supposing for argument's sake that I was planted here? ... What would have been your first duty as a loyal citizen?
Shattered Visage, the comic follow-up to the series has this: "Does the presence of Number Two require the existence of Number One?"
The final episode of Blackadder Goes Forth, already bleaker than the other episodes, had Baldrick ask one of these, specifically why World War I happened and why couldn't they all just stop fighting. Even Blackadder had no real response. Not long after, they all go over the top.
In the fourth season of Judging Amy, we get a particularly good example. After Kyle goes behind the other doctors' backs to make sure a patient gets the treatment she needs, the head doctor at the hospital calls him out on his maverick behavior and her disappointment in him:
Lily: Every time I think I'm getting closer to you, you do something stupid, or foolish, and I catch just a glimpse of what you must have been like before you got kicked out of med school.
In Game of Thrones, Varys tells a riddle to Tyrion about a king, a priest, a rich man, and a sellsword. Each of the first three ask the sellsword to kill the other two. Varys asks, who decides who lives and who dies. Tyrion immediately says the sellsword since he has a sword — the power of life and death. Varys then asks why people still believe that kings rule if the sword truly is the only real power in the world. Tyrion has no answer for this.
Later in the series, Tyrion, having had enough of Varys' secrecy, bluntly asks him what he wants. Varys turns it around and asks Tyrion the same question. Tyrion admits that, after being marginalized his whole life, he likes being the acting Hand of the King and is happy about being able to make a real difference in the world.
"No. You are an expert on the Klingon Empire. So, tell me, Advocate. Isn't it possible that there were no civilians on the transport Worf destroyed? Isn't it possible that the ship he saw was sending out false sensor images and that this whole affair was staged so that the only Klingon officer in Starfleet would be accused of a massacre and the Federation would be forced to stop escorting the convoys? Tell me, Advocate, isn't. It. Possible?
In "Tacking into the Wind," Worf discovers Gowron is setting Martok up to fail in battle to either get him killed or disgraced, making the war with the Dominion even tougher. Worf's attempts to resolve the problem fail, and he seeks advice from Ezri. She points out that Gowron is "a symptom of a larger problem": the Klingon Empire itself being corrupt. Worf initially disagrees, but Ezri asks him to name the last Chancellor he respected or one that didn't try to cover up a scandal. Her conclusion is what really gives Worf something to think about.
"Worf, you are the most honorable and decent man I have ever met. And if you're willing to accept men like Gowron, then what hope is there for the Empire?"
The same episode sees Kira trying to help Damar's new resistance movement against the Dominion. Damar is dealt a nasty blow, though, when he learns the Dominion hunted down and killed his wife and son.
Damar: What kind of state tolerates the murder of innocent women and children? What kind of people give those orders? Kira: Yeah, Damar, what kind of people give those orders?
In the final episode of M*A*S*H, Hawkeye is committed after an incident on a bus. The psychiatrist on hand has him relive the scene, where they were stopped at a checkpoint and needed to keep completely quiet, but a woman's chicken wouldn't stop making noise. He says she killed the chicken to keep quiet...but the doctor then asks "She killed the chicken?" This sparks Hawkeye's real memory, that she'd actually smothered her own baby to keep it quiet.
Hawkeye: You son of a bitch. Why did you make me remember that?
Doctor: You had to get it out in the open. Now we're halfway home.
In Red Dwarf, Kryten delivers one to the Inquisitor when making his case for existence.
Inquisitor: In a human, this behaviour might be considered stubborn.
Kryten: But I am not human. And neither are you. And it is not our place to judge them... I wonder why you do?
Argentinian cartoonist Quino made a strip about a man showing to his grandson his collection of books:
Man: By reading all these books I learned who were the Egyptians, Greeks, Romans, Babylonians, Incas, Mayas...
Boy: And we grandpa? Who are we?
(a moment later)
Mom: Where's your grandpa?
Boy: In the library, crying.
Linus does this in one Peanuts strip when he asks a doomsday prophet who has been terrorizing (or boring) the camp kids for a week: "Have you ever considered that you might be wrong?".
In one strip of Calvin And Hobbes, Calvin asks his father, "Dad, how do soldiers killing each other solve the world's problems?" His father has no answer for him.
Two from the arc where Calvin and Hobbes go to Mars to escape Earth's pollution: "Is that your candy wrapper over there?" and "Would you welcome a dog that wasn't house-trained?", both asked by Hobbes after Calvin litters on Mars. Calvin realizes he's part of the problem and he and Hobbes go home so as not to ruin things for the Martians, and partly out of the realization that as human habits cause pollution, it's not right to go to another planet to escape the mess they've caused on Earth.
In one Bloom County strip, Oliver Wendell Jones takes Binkley and Opus on a Mind Screw journey contemplating the nature of the universe, all the while asking "Why?" As the trip gets more and more out of control and Oliver keeps asking why everything is the way it is, Opus gets fed up and asks "Well, WHY NOT!?" which metaphorically brings Oliver back down to Earth.
On the July 11th, 2011 edition of WWE Raw, John Cena delivers one to CM Punk. Punk had spent the entire promo Moving The Goal Posts while talking over his contract to renew with the WWE and trying to win over the audience in the process. Cena comes out and hits Punk with a Kirk Summation, pointing out how big of a Hypocrite Punk is before asking him this question; if you love the WWE universe so much, why are you trying to leave the WWE? Punk, who'd been in full Magnificent Bastard mode all night, gets furious and tries to lay the blame on Cena, but the fact he'd just been offered the very things he'd been complaining about Cena having and more but still hadn't gotten enough to stay in the WWE renders him unable to effectively answer this.
Punk would then piss off Cena, by deriding his claim of being the underdog. He stated that Cena, like his hometown of Boston, has long since become a dynasty, comparable to the New York Yankees. Cena, unable to argue against that claim and angered over the comparison, promptly decked him in the face.
During their 2010 feud in DGUSA, Jimmy Jacobs (at the time an atoning for his past sins) confronted Jon Moxley and tried laying one of these on him combined with Not So Different: "When I look at you, I just see myself in the mirror... Whole life's a struggle, isn't it? Keep fighting. Keep fighting, then what? Then what?"
In Mage The Awakening there is a spell called "The Inescapable Question" which has the capacity to cause any question to cause the hearer to stop and ponder its meaning and answer (it is noted that particularly savvy mages can get the effect by simply asking "Why?").
Hunter The Vigil: vampires around the world will crap their pants upon receiving a piece of paper, or an SMS, or an email, or a phone call, that asks "Who is Cain?" This isn't necessarily because of the significance of Cain; it's because it means the Cainite Heresy is coming for them.
In Hunter The Reckoning the redeemers have this power. They can ask a question, although what exactly the question is and if the monster answers, is not of much relevance. As long as the hunter appeals to the humane side of the target they bring it forward and the creature is overcome with possibly forgotten feelings and emotions of being alive and mortal. The book states that a common question is "Do you remember?"
The Dark Champions villain known as Dr. Enigma has a similar power called The Unanswerable Question that can leave a person in a helpless daze. He touches the victim with a chemical and then asks a bizarre question such as "Why must two and two make five?" or "What color is Tuesday?"
BioShock: "In the end what separates a man from a slave?" note A man chooses. A slave obeys. (It turns out the Player Character has been conditioned in their childhood so they really haven't really been choosing along the way. In fact, this is one for the player too.)
These are a critical element of Wadjet Eye Games' The Shivah. Rabbinic Q&A duels come up multiple times in the game.
One could argue that finding these is pretty much the entire point of gameplay in the Ace Attorney series, since you're trying to peel away lies to uncover truths in the courtroom. Appropriately, the people being asked often react as if they've been physically pierced by the questions.
In Ace Attorney Investigations 2, the new "Logic Chess" system involves having a verbal battle of wits to draw a secret out of someone by way of Dialogue Trees rather than presenting evidence and pressing statements. Hits hardest with the final opponent, Yumihiko Ichiyanagi, when the point of the final round turns out not to be a push to acquire any case-relevant information, but to help find a cause that's enough for a completely broken individual to go on living for.
The player is actually treated to one of these at the end of the second Phoenix Wright game: is it right for a murderer to get off scot-free, in order to protect the life of a completely innocent bystander? (In context, this also amounts to "what is justice?" and "what does it really mean to be a lawyer?") As one player put it, "I have never been so paralyzed by a simple yes-or-no question in a video game."
In Dragon Age: Origins, a conversation between the Dalish Elf and a Chantry Priestess at Ostagar, where they call her on claiming that the Maker only desires peace and love when His Chantry branded the Dalish as heretics, lead an Exalted March against them and destroyed their homeland.
Dalish Warden: You administer blessings to Elves?
Priestess: Of course. The Maker accepts all those who would hear him.
Dalish Warden: And does he steal the Homeland of those who don't?
In one of the final Missions of Grand Theft Auto IV, Niko Bellic finally accomplishes his reason behind moving from "the Old Country" to Liberty City. He's finally tracked down his old war buddy (and the word "buddy" is used loosely) that sold out their troop and resulted in almost their entire squad being slaughtered like pigs, all so the traitor could get money to buy drugs with. Needless to say, in the conversation that follows As shown below), an armor piercer is shot at Niko, that actually effects him...for about five seconds.
Niko Bellic: Strange choices?! How much?! Darko Brevic: (laughing) A thousand. Niko Bellic: (Close to tears) You killed my friends for one thousand dollars? Darko Brevic: (laughing) How much do YOU charge to kill someone? Niko Bellic: (pauses) You ruined me, you fuck!
Mona Sax: What are you so afraid of? What do you want from me?
Max Payne: [narrating] The things I want, by Max Payne. A whisky, a smoke, for the sun to shine. I want to sleep to forget, to rewrite the past, my wife and baby girl back, unlimited ammo and a license to kill. More than anything at that moment I wanted her.
In Star Control 2, there is only one question that can get any meaningful response out of the Ur-Quan Kohr-Ah. While this won't let you avoid fighting them in the game, the first time it was posed to them in the backstory (by the Mael-Num), it locked them up long enough to allow for an escape.
To clarify, it locked one side long enough to other show up. 'The Words' are a simple plea: "Hold! What you are doing to us is wrong! Why do you do this thing?". Both sides come to total stop when they hear it, causing them to justify their actions. The Kzer-Za more quickly explain themselves, while the Kohr-Ah will give the prey who asks substantially more time.
Mass Effect has a question that spurs a centuries-long war that drove an entire species from their planet: "Does this unit have a soul?"
Shepard: They sound like wonderful people. The galaxy is lesser for their loss.
Erinya: Yes, it is.
Shepard: Do you think they'd want you to do this? (*Asari has a meltdown*)
Shepard ends up on the receiving end of more than a few of these due to his-or-her affiliation with Cerberus throughout the second game. Even one of the game's minor villains gets to call bullshit on Shepard's holier-than-thou attitude because of this.
In general, Shepard uses a LOT of these when persuading people, and sometimes regularly in dialogue to keep events moving.
In Mass Effect 3: "Does this unit have a soul?" Which, depending on whether or not you end the war that started with the same question, makes this an EXTREMELY Armor Piercing Question.
During the trial scene in Neverwinter Nights 2, most of your dialogue is composed of these. Your Diplomacy/Taunt/Bluff checks determine the reaction of the opposing lawyer; successes on Taunt checks get really silly angry responses.
"What can change the nature of a man?", a riddle asked by the Night Hag Ravel Puzzlewell, in Planescape: Torment. Ravel killed all those who couldn't give the right answer. As it turns out, her right answer wasn't a 'what' but a 'who': She only wants The Nameless One's answer, because the first incarnation was the one who gave her the question in the first place and she still hasn't found an answer herself. The question essentially drove Ravel to mull over it for an unknown number of millennia and slowly drove her mad.
In Resonance of Fate, this happens to several people at various points, actually, but perhaps the harshest of which is- again- the bridge scene, posed by Lagerfield to Zephyr.
"Tell me! Why did you live while they died? Is your life worth more then theirs?"
In Knights of the Old Republic, you infiltrate the Sith Academy and meet a woman with a tragic past that made her receptive to the Sith philosophy. She was enslaved and abused. She finally escaped and originally trained as a Jedi. However, she wanted revenge for all that was done to her and other slaves. Here is part of the dialogue tree that leads to her beginning to question the ways of the Sith...
Yuthura: I wanted to use the Force to free the other slaves I knew, to fight for what I knew was right. The Jedi restrained me until I couldn't stand it any more. They claim the dark side is evil, but that isn't so. Sometimes anger and hatred are deserved and right. Sometimes things change because of it.
Yuthura: Any failure to get the results I want is due to a lack of power on my part. That can change, in time. As a Sith, my mettle is tested far more than when I was a Padawan. I know this may sound strange, but only my compassion stands in my way, now. Once that is gone, let the slavers beware.
Player Character: But...if you lose your compassion, will you still care about those slaves?
Yuthura: [sounding unsure] I...yes, of course. I—I mean...losing my compassion as in...holding back...
The sequel has a question that can be delivered as the punch line to a series of speeches to erode the will of The Dragon:
The Exile:Sion... Your life... Was it worth living? Darth Sion: ...It was not. No matter how many Jedi I killed... No matter how many lay broken at my feet... The pain would not end. I am glad to be rid of this place.
The amazing scene in Final Fantasy XIII where Hope finally musters up the guts to confront Snow about his mother's death (which he unwillingly contributed to) consists mainly of a barrage of armor-piercing questions that bring the resident Idiot Heroonto his knees in despair. Said questions include "What happens when your actions end up ruining someone's life?" and "How do you pay for what you've done?"
Notably, it is not asked by or to the player character: Ulysses asked it of the Think Tank. This almost caused disaster: it led to the Think Tank trying to break out of the Big Empty rather than being more-or-less confined there.
Though the player can choose to turn this question around on Ulysses during the final battle, though one has to show him that they understand the meaning behind it for it to work.
In Sengoku Basara: Samurai Heroes, Motonari ends up asking Misanthrope Supreme Yoshitsugu about whether his stated goal of bringing misery to all humans includes bringing misery to Yoshitsugu's Morality Pet, Mitsunari. Yoshitsugu, who hadn't even considered the thought of having a human he does not hate up to that point, gets completely stumped.
Runescape has one from the finale of the goblin quests. The god of war has possessed your friend, Zanik. During the fight, she can regenerate indefinitely thanks to said god's power. At one point, she says she has to kill you because humans are the enemy. The player asks her: "but am I, your enemy?"
In The Elder Scrolls V Skyrim, Paarthurnax will respond to the Blades' demands that he be killed with dignity and admits that Dragons like himself aren't exactly trustworthy beings and that he is trustworthy only due to tremendous effort — he fights his tyrannical urges every day. He invites the Dragonborn to ponder one question, one that has actually made many players hesitate to kill him: "What is better - to be born good, or to overcome your evil nature through great effort?"
In Star Wars: The Force Unleashed, Juno Eclipse asks Starkiller why he defied his master Darth Vader and saved her. Starkiller awkwardly answers that he needed her to fly his ship, but she retorts that they both know that isn't true. This foreshadows that Starkiller has feelings for Juno, and that he is slowly becoming a hero instead of Darth Vader's servant.
Makoto: "Different? Uh... The difference..." *beat* "...I'm not..." *begins crying* "I'm not different from anyone else! I'M NOT! I wanna be the same! I just wanted to be the same..."
In World of Warcraft, during the legendary quest chain in Mists of Pandaria, after you head off with Wrathion to use the Thunder Forge as part of your plan, he will ask you if you, by blindly trusting a black dragon in pursuit of power, are any different from Garrosh- who is the enemy of the Alliance and is quickly becoming the enemy to the Horde through his increasingly corrupt and immoral actions.
Inverted in Katawa Shoujo when Rin answers a question from Hisao, leading him to realise something worrying about himself:
Hisao: Remember that sketch you made of me? How you said I looked grim and gloomy or something? I'd like to know what you meant by that.
Rin: Well, you see... We've known each other for two weeks and I've haven't seen you smile even once.
Later on in Rin's route, as Nomiya is angry about Rin walking away from the exhibit and Hisao questions whether the commitment is worthwhile, Nomiya asks Hisao if he has anything comparable to Rin's passion for Art. Hisao, who may or may not have left the club by this point, based on player decisions, silently concedes that the answer is no.
Also, asking one of these of Rin is the key to getting her good ending. Rin laments that what she really wants is for someone to understand her well enough to not have to ask her questions; Hisao asks, "But if you found someone like that, then what?"
Jigoro asks Hisao, in response to him suggesting that he visit his daughter Shizune at Yamaku, ends up asking Hisao when the last time he's called his parents. Hisao is forced to concede that he hasn't done a very good job of keeping in touch with them; other routes show minimal, and usually off-screen contact with them.
A Profile's second route has Miku as the heroine, who is prone to asking Masayuki questions he really doesn't want to answer about his study habits and how he quit track. The answer that he doesn't want to admit is that he really misses being on the track field. Before this, people were too afraid to mention it in front of him.
Youhei, of all people, gets one of these in Kyou's route in CLANNAD, when he forces Tomoya to confront the fact that the Fujibayashi sister he is dating is not the one he actually cares for.
TT: Have you ever looked into the sky without your shades?
When Terezi starts sharing her concerns and doubts with Dave, he is unsure how to respond. He finally asks "Do you want me to tell you to be a better human or a better troll?" She avoids actually answering the question.
Lil Hal springs one of these on Dirk when the latter is attempting to kill him.
It may be subjective, as it's an all-caps comic, but there seemed to be an undertone of intense worry there; "Yes! Of course the glass plates we're eating off of are clean. We use only the finest window cleaner on them... Oh Crap."
Ménage à 3: Kiley to Sonya. "So how long have you had these latent homosexual urges?"
Slightly Damned: Without quite realizing it, Sammy asks Kieri to think about Buwaro's feelings for her, and their recent falling out. The question... stings.
Spina Cage: "Hasn't anyone ever depended on you?" seems to be one for Joven.
Darths & Droids: While Obi-Wan and Yoda are discovering the Jedi Temple massacre:
Ben: Sally, this is serious. You need to play it seriously.
Sally: Just because you do everything Dad tells you to!
Ben: What? No I don't!
Sally:Why are you studying medicine then?!
In Webcomic/Angels2200, Quetz ends up asking this to herself. When Hammer sneaks into her hospital room to check on her, Quetz rather than being appreciative or even concerned for Hammer, contemplates pressing the call button on her bed to summon help in an attempt to get Hammer caught and removed as commander of Icebreaker Squad, unaware that they already know she's in here because of surveillance cameras. Hammer talks Quetz down by telling her that if she betrays her, no one in Icebreaker will want to follow her. Quetz then questions herself as to why she didn't press the button, and ultimately concludes that it's because she wants to belong.
In his phone call to the director of My Pet Monster, The Nostalgia Critic's self-loathing starts to seep in when he gets asked why he's in his twenties and is still watching kid movies.
In Hitherby Dragons, this is the method ii Ma uses to trap others within the Place Without Recourse. They are given a question that they cannot answer without negating everything they believe in — and while that question remains unanswered, they're left in a place where nothing they can do matters at all.
Towards the end of Cats Dont Dance, the animals are telling Danny how much Hollywood sucks for them and how miserable all of their lives are. Danny responds with "Then why are you still here?" causing all of the other animals to go into stunned silence.
("Who are you angry at?") Delivered by Azula and her friends to Zuko in "The Beach".
Also: "Then I have a question for you... what are you gonna do when you face my father?"
There's also a Shout Out to Babylon 5: "Who are you, and what do you want?" Delivered by Iroh to Zuko in "Lake Laogai".
From an exchange between Iroh and Zuko, after finding Aang's Air Bison.
Iroh: What do you plan to do now that you have found the Avatar's bison? Keep it locked in our new apartment? Should I go put on a pot of tea for him? Zuko: First I have to get it out of here. Iroh: [losing his composure for probably the first time ever] AND THEN WHAT?! This is exactly what happened back at the north pole! You had him, and then you had nowhere to go!!
"Where is my mother?"
Done in the Justice League Unlimited episode Patriot Act. An old woman asks a mutated superpowered General Eiling, who had previously taken a serum to gain superpowers, and engaged in a battle with several 2nd, 3rd, and 4th string JLU members with no powers, exactly how many people without superpowers he was going to have to kill in order to save people without superpowers. Followed up with an armor piercing answer when a child responds to Eiling's accusation that superpowered people were a threat by pointing out that he was the only one in the vicinity with actual super powers. General Eiling admits that he has become what he sought to destroy and retreats.
Done earlier in the Justice League episode 'A Better World' from Batman to Batman. The Justice Lords took complete control of their world to eliminate crime, and Batman has this exchange with his counterpart after apparently surrendering to him, and (while parked at a stoplight) witnessing a citizen being taken away by the police for arguing over a restaurant check.
At the end of Ben 10: Ultimate Alien episode, Solitary Alignment, George asks Ben if people doubt his heroic ability as much as they do George's, Ben agrees and stops fighting and they come to a compromise. Ben will get Ascalon if George is defeated.
At the conclusion of the Gargoyles four-part episode, "City of Stone," the Weird sisters ask a series of Armor-piercing questions to Macbeth and Demona. They convince Macbeth to spare Demona's life by asking him about times in his life when murder never solved any of the problems it should have. They convince Demona to give up vital information by asking her whose actions led to her clans' demises (hint: it was hers). Unfortunately, Demona is so deluded that the revelation doesn't last long.
Hudson once said to Xanatos: "Growing old terrifies you, doesn't it?"
Another one from the same episode: "Demona and Macbeth are immortal. Are they happy?"
Kilowog: We know what you're fighting against, kid, but what are you fighting for?
Wreck It Ralph to Sour Bill after discovering a vital clue about Vanellope Von Schweetz and the ensuing conspiracy in her game "Sugar Rush": " If Vanellope isn't supposed to exist, why is her picture on the game console?"
Rarity does this to her sister Sweetie Belle in the My Little Pony: Friendship Is Magic episode "Ponyville Confidential" upon discovering that, in their pursuit of their talent and destiny declaring Cutie Marks, Sweetie Belle and her friends have been writing a slanderous gossip column.
Rarity: Do you really think that writing nasty things and making everypony feel horrible is your destiny?