I was planning to make it a full couple of scenes, but my muse is in a fickle mood, so here's what I have.

Bridge Scene, Act 1

Q: "What is your name?"
A: "I'm Kel-Agent Kelly Fallow. Nice to meet you!"
Q: "...What is your quest?"
"Um...I guess it's to meet new people and get to know more about them. Oh, and protect the canon. What about you?"
Q:"What?"
A:"Why stand around next to a a bridge on the middle of nowhere. I mean, you can't get that many visitors and it's pretty cold. Don't you get lonely?"
Q:"No! Well, somet-"

Bridge Scene, Act 2

"What is your name?"
"Agent Gall, Department of Floaters. PPC. Out of the way...please."
"What is your quest?"
"Kill the Sues, save the canon, and get a paycheck for once. Look, I don't have time for this."
"What is the average lifespan of the American speckled trout?"
"What? What kind of a question is thaaaaaaaaaa-"

Dafydd

Keeper: What is your name?
Dafydd: Dafydd Illian.
[Dafydd is flung into the chasm]

Constance

Keeper: What is your name?
Constance: Constance Illian.
Keeper: What is your quest?
Constance: To fish my husband out of that hole you've just chucked him into.
Keeper: What is your favourite colour?
Constance: Black.
Keeper: All right, off you go.
Constance: Who said I'm crossing? I can fish from here.

Dafydd, Take 2

Keeper: What is your name?
Dafydd: Maglor Feanorion.
[Dafydd is flung into the chasm]

Lou

Keeper: What is your name?
Lou: Louise. The rest is none of anyone's business.
Keeper: What is your quest?
Lou: Honestly? To answer your questions for the entertainment of the readers.
Keeper: ...
Lou: Well, you asked.
Keeper: What is the meaning of life?
Lou: Try and be nice to people, avoid eating fat, read a good book every now and then, get some walking in, and try and live together in peace and harmony with people of all creeds and nations. (Source)
Keeper: ...
Lou: When your author has access to Google, there's not a lot of questions you can't answer appropriately.
Keeper: ... did you just say a hyperlink?
Lou: You're out of questions. But yes.
[Lou crosses the bridge]

Dafydd, Take 3

Dafydd: Do I have to?
Constance: Yes.
Dafydd: Really?
Constance: Unless you never want to get home.
Dafydd: Well, you know, this is a nice place, we could live here...
Constance: Elf-boy. Go. Now.
[Dafydd approaches the Keeper]
Keeper: What is your name?
Dafydd: Canafinwë Makalaurë, son of Curufinwë Fëanáro.
Keeper: What is your quest?
Dafydd: To get home in time to feed my fire lizard and read my son a bedtime story.
Keeper: What will you do if I throw you into the chasm again?
Dafydd: ... set my wife on you. Do you really want that?
[They both look at Constance, who is nonchalantly sharpening a dagger]
Keeper: ... you may pass.
Dafydd: Thanks so much.

Constance, Take 2

Keeper: What is your name?
Constance: I already answered.
Keeper: Oh, right - got a bit carried away there.

Narto

Keeper: What is your name?
Narto: Narto Telyan.
Keeper: What is your quest?
Narto: To cross this bridge because Lou told me to.
Keeper: What is the relationship between you and Lou?
Narto: What sort of relationship do you mean? I mean, we're not relatives or anything, but we have a spatial relationship, a temporal one, we were partners, we- well, you're going to have to clarify.
Keeper: What? I don't even understand what you just said!
[The keeper is thrown into the chasm]
[Narto crosses the bridge halfway, and meets Lou. Narto leans over the side]
Narto: Married, by the way!
Lou: Sort of married.
Narto: So is Diane 'sort of' our daughter?
Lou: You don't have to be married to have kids, Gingernut.
Narto: Really? How fascinating! Do tell me more!
[Exit all]

hS

TOS

Bridge Keeper: What is your name?
Kirk: James Tiberius Kirk.
Bridge Keeper: What is your quest?
Kirk: A five year mission to explore the galaxy.
Bridge Keeper: Which uniform do you think you look the best in?
Kirk: The gold one. But…my Mirrorverse uniform is very sexy… (gets thrown off bridge)

Reboot

Bridge Keeper: What is your name?
Kirk: James Tiberius Kirk.
Bridge Keeper: What is your quest?
Kirk: A five year mission to explore the galaxy.
Bridge Keeper: Will you sleep with Mary Sue?
Kirk: Is she hot?
Bridge Keeper: Incorrect.
(Kirk falls off bridge and lands next to another man)
Shatner!Kirk: Hello, my younger self. Did they ask you the uniform question too?
Pine!Kirk: No, they asked me whether I'd sleep with someone called Mary Sue.
Shatner!Kirk: Did you say…yes?
Pine!Kirk: No, I asked if she was hot.
Shatner!Kirk: They're always hot. But…don't sleep with them. They're…parasites. They drain away your personality, until you are unfit to command, then take command of the ship and lead you to disaster. Do not fall in love with the the Mary Sue.
Pine!Kirk: Thanks. I guess.
Shatner!Kirk: Don't mention it. If you ever need tips for removing them…contact Spock Prime. We faced down many of them.
Pine!Kirk: I'll keep that in mind.
(They work together to climb out of the chasm, meeting their respective Spocks)


Both Reboot and TOS

Bridge Keeper: What is your name?
Spock: Spock.
Bridge Keeper: What is your quest?
Spock: Currently, to find my captain.
Bridge Keeper: May I have your autograph?
Spock: No. (He pulls out a slip of paper and a pen, on which he writes his name. He then hands it to the bridge keeper.)
Bridge Keeper: You were wrong.
(Spock jumps off the bridge to find Kirk)

Bridge Keeper: What is your name?
McCoy: Leonard McCoy. Kirk calls me Bones.
Bridge Keeper: What is your quest?
McCoy: At the moment, to get over this bridge so I can go back and get Kirk and Spock.
Bridge Keeper: How do you play a chord on a violin?
McCoy: Dammit, man, I'm a doctor, not a musician!
Bridge Keeper: That is correct. You may go.
McCoy: …All right then.

TNG

Bridge Keeper: What is your name?
Data: Data.
Bridge Keeper: What is your quest?
Data: To become more human.
Bridge Keeper: What does it feel like to be angry?
Data: I do not know. (holds up hands to prevent keeper from pushing him off) You asked that question because you thought that, as an android, I would be incapable of answering it correctly. However, I have asked humans that very question, and no one has been able to give a satisfactory answer. Therefore, the question is invalid. (pushes keeper off)

DS9

Bridge Keeper: What is your name?
Odo: People call me Odo.
Bridge Keeper: What is your quest?
Odo: To keep order on the space station known as Deep Space Nine.
Bridge Keeper: Can you shapeshift into something for me?
Odo: No.
Bridge Keeper: Haha! I said can you, not will you!
(Odo rolls his eyes as he's pushed off the bridge. Some time later, a smug looking bird is seen flying across the chasm.)

Bridge Keeper: What is your name?
Bashir: Julian Bashir.
Bridge Keeper: What is your quest?Bashir: Currently, to get across this bridge.
Bridge Keeper: Are you in an ersatz homosexual relationship with Garak?
Bashir: Ah, er…no, why do you AAAAAASK! (falls off bridge)

Bridge Keeper: What is your name?
Garak: Garak. Plain, simple Garak.
Bridge Keeper: What is your quest?
Garak: At the moment, to get across this bridge.
Bridge Keeper: Are you in an ersatz homosexual relationship with Bashir?
Garak: Yes.
Bridge Keeper: You may pass.


If I come up with more, I'll post them.

[Before you lies a misty chasm, and across it stretches a rickety bridge. The far side is shrouded by the fog, but by the near end waits a short, tattily-clothed man... the bridge keeper.]

The one trying to pass the bridge is an old man. He walks confidently towards his end of the bridge, unperturbed by the sight that is before him. He sense no ill-will from this so-called bridge keeper. Perhaps he will entertain the bridge keeper for a while, if only to know more of his purpose.

"Now, my good man, can I pass through this bridge? I am in dire hurry, for someone may have need of either my counsel or aid, or both."

"NAY!" shouts the bridge keeper, "I will only let you pass if you answer the questions three."

The old man simply nods in agreement.

1. What is your name?

"I am known by many names, my good friend. It is rare for anyone to ask of it, instead preferring to give me names instead. For now, let me be known as Storm Crow."

2. What is your quest?

"I have many quests, for my duty stretches beyond one land,or nation, or people. I may even have duties that far into the future, that I may have not remembered yet. An old man, you see."

"In fact, I may even found out that my dire need to hurry is useless, as the people that I am in hurry to help have either settled their problems, or even that the problem hadn't occured yet, and their fate makes the problem didn't happen."

The bridge keeper finds this information to be more of a puzzle than an answer. "Then why are you in such a hurry? You didn't know whther the people that you want to help may need it or not."

The old man simply chuckles, "Well, do you?"

"No, AAHHH!!!", and the bridge keeper magically launched from his standing point.

3. A random question (the more random/hilarious the better).

The bridge keeper soon climbs back to his side of the bridge. He brushes off the dust of his cloak. He smiles sheepishly at the old man, embarrased by his last flight. "A final question. What is the height of Minas Tirith?"

"The one in the First Age or the Thrid Age?"

"How do I know?". Again, another free improptu flight ticket for Mr. Bridge Keeper.

Gandalf simply shakes his head. "Radagast must think that my pipeweed is addling my mind if I told him about this."

Marvin

Keeper: What is your name?
Marvin: Marvin Jones.
Keeper: What is your quest?
Marvin: To protect Equestria from Glitter Dos.
Keeper: Who is Best Pony?
Marvin: Fluttershy. No, wait, Twilight! *Flung into chasm* AAAAAAAAHHHHHHH!!!
Keeper (looking down into pit): The correct answer was Rarity.
Marvin (still falling): Liiiiieeeessss!

Printworthy

Keeper: What is your name?
Printworthy: Printworthy.
Keeper: What is your quest?
Printworthy: To protect Equestria from the negative effects of bad writing.
Keeper: What...is the plot of the next Daring Do book?
Printworthy: I really should not tell you; spoilers and such.
Keeper: Oh come on, please? I loved the other books, and the last one left me with so many questions! Here, tell me the answer, and I'll fish out your partner from the chasm for you.
Printworthy: Well, missions have taken up so much of my time, so I don't have a full grasp on the plot, but I do have a general idea. Fine, come closer, I'll tell you what I have at the moment.
*Keeper comes in closer to Printworthy, who whispers into his ear.*
Keeper: Wow. That's brilliant! Thank you so much!
Printworthy: You're welcome. Now, my partner?
Keeper: Oh, yes, one moment.
(The Keeper pulls on a rope on the bridge, causing the chasm to spit Marvin back out.)
Marvin: AAAAAAHHHH!!
Keeper: There you go, one partner and a pass for two across the bridge.
Printworthy: Thank you. Come along, Marvin.
Marvin (to keeper): *groan* Go bugger yourself.
Keeper: I get that a lot.

Jumper

Keeper: What is your name?
Jumper: Well, I have gone by a lot of names over the source of my life, but I am most currently attached to Jumper.
Keeper: Fair enough. What is your quest?
Jumper: To explore the multiverse, and currently as a sort-of side quest, protect it from badfic.
Keeper: What is the source of all magnetism?
Jumper: What was that?
Keeper: What is the source of all magnetism?
Jumper: *thinks for a long while* I would say...The Creation of the Universe.
Keeper:...Well that's not what I am looking for, but I suppose... Go ahead.
Jumper: Thank you.
Keeper: Hmm. I suppose that was a little ambiguous... Oh bugger. *Flung into chasm*
((The real answer to this last question is moving electric charge.))

(Agent Peregrin approaches the bridge, absentmindedly performing an ancient chant)

Bridge Keeper: To cross this bridge, you must correctly answer three questions.

Peregrin: (takes out a pencil and a notebook) I will attempt your questions, though we may be here for some time if any of them relate to geometry. It has been many years since I have studied that field.

BK: What is your name?

Peregrin: I am Peregrin.

BK: What is your quest?

Peregrin: Hmmm ... To research and repair the various kinds of poor fanfiction that persist throughout the multiverse.

BK: Final question then. What are the digits of pi between the 762th digit after the decimal point and the 803rd?

Peregrin: (immediately) Inclusive or exclusive?

BK: I should have specified. Darn. *flies into chasm*

Peregrin: That was unexpected. *crosses the bridge* However, it was quite fortunate that I did not actually have to answer that question. It has been, oh, a century at least since I last was punished with Chapter Four.

Some time later, Agent Tomash approaches the bridge, looking for his partner.

Agent Tomash: You haven't seen my partner, Agent Peregrin, have you? I think he's forgotten what our RC number is again.

Bridge Keeper: To cross my bridge, you must answer three questions correctly. If you fail, you will be thrown into that Imposing Chasm.

Tomash: Sure. Once I do that, can you tell me where Peregrin went?

BK: (in his best Evil Interrogator voice) I'm asking the questions here!

(aside) I've always wanted to say that line.

(in his earlier tone) Well then, what is your name?

Tomash: Tomash, these days. Next question, then?

BK: What is your quest?

Tomash: To fix bad fanfic. Oh, and to find my partner when he wanders off.

BK: That was two quests, but you had the right answer in there, so I'm letting it slide. For your last question, then, what is two plus two?

Tomash: I'm going to channel Peregrin here to make sure I get this right, so what base? I'd think base 10, but your question is a bit ambiguous.

BK: No! Don't say that word! *flies off into the chasm, shouting "Base 10!"*

Tomash: Well, then the answer's four. (He crosses the bridge, where he finds Peregrin.)

Tomash: Peregrin! I've been looking for you. We have a mission!

Peregrin: (lost in thought) Oh. Right. We do. I left the RC in order to gather supplies for our mission, but I seem to have become lost. Do you remember our Response Center number?

Tomash: It's 112358. Let's head back. We have work to do.

The pair wanders off, with Peregrin giving a lecture on some old research of his to distract himself and his partner.

It was too fun the first time, now let's throw in some more OCs.

Krieg:

Keeper: WWWHAT is your name?
Krieg: Me? Well, Ich heiße Krieg Himmel.
Keeper: ...Wwwhat?
Krieg: Ach, warum niemand sprechen meine sprache? I am Krieg.
Keeper: Then WWWHAT is your quest?
Krieg: To offer the services of myself and my gesellschaft to the highest-paying employer. I am a mercenary, you see.
Keeper: WWWHAT are the names of the fallen angels of Christian faith?
Krieg: ...Rather a large number of fallen angels, don't you think? It was a rather brutal uprising, after all.
Keeper: ...Well, yes, but- AAAGH!
*Keeper is launched into chasm*
Krieg: Tsk. Das wäre nicht passiert, wenn die Regeln nicht zu meinen Gunsten manipuliert haben. ("This would not have happened if the rules were not rigged in my favor.")

~

Gabriel Iscandrioc:

Keeper: WWWHAT is your name?
Gabriel: ...Yeah.
*Gabriel flaps his wings and launches himself across the bridge with such force that it blasts the keeper into the chasm *
Gabriel: It's "Gabriel," by the way!

~

Sable Cross:

Keeper: WWWHAT is your name?
Sable: Sable Cross, sir.
Keeper: WWWHAT is your quest?
Sable: Well, I am a Hero, of Estrelain. My quest is to protect the land with my immortal life until I am no longer needed.
Keeper: WWWHAT are your policies regarding recession and employment in your kingdom?
Sable: You'd have to ask my wife, the Queen. I was only king for as long as it took to place my family securely in power, and then I stepped down.
Keeper: Wait, how does that even WOOOOORK!!!
*Keeper is thrown into chasm*
Sable: I don't know either; I was only king for a day!


is there for you to gain

Florestan

Keeper: What is your name?
Florestan: It's Florestan.
Keeper: What is your quest?
Florestan: To scream at bad fanfics.
Keeper: What... is the best way to relieve stress in the morning?
Florestan: Um... Does sex count? 'Cause that's kind of a broad question, don't you know?
Keeper: Hm... yeah, it is a bit of a-- *is flung off the bridge*
Florestan: *sighs* Finally! I swear, if I got launched into that chasm one more damn time...

Eusabius

Keeper: What is your name?
Eusabius: It is Eusabius.
Keeper: What is your quest?
Eusabius: To review bad fanfics.
Keeper: What was the name of the virtuoso pianist who was also a composer and wrote piano concerti?
Eusabius: Would you mind perhaps disambiguating a little?
Keeper: What do you mean?
Eusabius: Was this pianist alive during the Romantic era, or the Twentieth Century? The difference is quite distinct, I trust you understand.
Keeper: Hm... You know, that's a good questio-- *is flung into the chasm*
Eusabius: What a strange encounter... *walks off*

Anneli Rodriguez

Keeper: What is your name?
Anneli: Oh hey, a new guy! Uh, I'm Anneli Rodriguez.
Keeper: What is your quest?
Anneli: Like, it's totally to seek the Holy Grai... Wait, no, it's totally to-- *is flung into the chasm*
Keeper: Aw, darn. I didn't even get to ask her what her favorite color is!

Cinderella

Keeper: What is your name?
Cinderella: Cinderella, my good sir.
Keeper: What is your quest?
Cinderella: To defend the multiverse from bad fanfiction, of course.
Keeper: What... is the one hundred and forty-third element on the periodic table of elements?
Cinderella: What kind of question is that? Even I know the periodic table of elements doesn't go that far, and I never got a muggle's education!
Keeper: *scoots to the side* You may pass.
Cinderella: *blinks* Oh... Uh... Thank you... *passes*

Xanthus Garkaran

Keeper: What is your name?
Xanthus: It's Xanthus Garkaran.
Keeper: What is your quest?
Xanthus: To beat the crap out of Mary Sues and Gary Stus. Why?
Keeper: Does it matter why?
Xanthus: Not really. It did waste your third question though, so I'll just take my time to cross this bridge now if you don't mind. *walks across the bridge*
Keeper: ... Damn it!

Keeper: What...is your name?
Steve: Steve Rogers, Captain in the US military. I'm also known as Captain America.
Keeper: What...is your quest?
Steve: To cross this bridge and catch Loki, so we can get him to tell us where the Tesseract is and keep him from invading Earth with an army of aliens.
Keeper: What...do you have to say about those who believe you and Iron Man are attracted to each other?
Steve: Wh-what?! People think that?!

Keeper: What...is your name?
Tony: You know who I am.
Keeper: What...is your quest?
Tony: To catch Loki and get the Tesseract back so I can find Pepper and do all that stuff she promised.
Keeper: What...did Pepper promise you?
Tony: Well, she...wait. My suit can fly. Why am I just answering your questions? *rises off the ground* Later, man.
Keeper: But...but I've been dying to know!

Keeper: What...is your name?
Thor: Thor Odinson.
Keeper: What...is your quest?
Thor: To find my brother Loki and return him, and the Tesseract, to Asgard.
Keeper: What...is your favorite Midgardian food?
Thor: Hm...it is hard to decide... *flies into chasm*

Keeper: What...is your name?
Bruce: Dr. Bruce Banner.
Keeper: What...is your quest?
Bruce: To retrieve the Tesseract for SHIELD, I guess.
Keeper: What...is the total output in gamma radiation of the Tesseract since the moment it was stolen to now?
Bruce: Depends on what point you think it was stolen at.
Keeper: What?
Bruce: Was it stolen when Loki got away, or when he first had one of his mind-controlled goons pick it up?
Keeper: *flies into chasm*
Bruce: *glances over bridge, shrugs, crosses*

Keeper: What...is your name?
Natasha: Natasha Romanoff. Codenamed Black Widow.
Keeper: What...is your quest?
Natasha: To save Clint. And retrieve the Tesseract.
Keeper: What...happened in Budapest?
Natasha: Sorry. That's confidential.
Keeper: Come on. Please?
Natasha: No. *crosses bridge*

Keeper: What...is your name?
Clint: Clint Barton, also Hawkeye.
Keeper: What...is your quest?
Clint: To shoot Loki in the face.
Keeper: What...do you think you're doing?!
Clint: Pointing an arrow at your face. You have five seconds to step aside or I shoot you.
Keeper: *hurriedly moves out of Clint's way*
Clint: *lowers bow* Thank you. *crosses bridge*

Keeper: What...is your name?
Loki: Loki, rightful King of Asgard.
Keeper: What...is your quest?
Loki: To lead the Chitauri in the conquest of Earth.
Keeper: What...silver tongue turned to lead?
Loki: That's not even a question, you buffoon!
Keeper: *flies into chasm* IT WAS WORTH IIIIIIIIIIT...
Loki: *snarls and stalks across bridge*

Agents first.

Ellipsia
Bridge Keeper: What is your name?
Ellipsia: Ellipsia...
Bridge Keeper: What is your quest?
Ellipsia: I want to prevent Suvians from enslaving innocent canons.
Bridge Keeper: What's a Paladin?
Ellipsia: Uh... depends on what kind of Paladin you mean. You weren't really clear on that.
Bridge Keeper: *gets flung into the chasm*
Ellipsia: *walks over*

Nathan
Nathan: Would you have thrown her off if she had answered with "I'm not entirely sure?"
Bridge Keeper: *crawls back onto the bridge* I'm not entirely sure. *wrings his clothes* What's your name?
Nathan: Birth name? Before or after my mom married again? Forum handle? Is this how I get you to-
Bridge Keeper: *is flung off again*
Nathan: Ha! I like that. *walks over*
Ellipsia: That was mean.
Nathan: Eh.

Saline
Bridge Keeper: What's your name?
Saline: Saline. S-A-L-I-N-E. Not Sallin, not Salin, not Salline, or whatever name pops up in my family.
Bridge Keeper: What's your quest?
Saline: I'm trying not to get bored.
Bridge Keeper: ...are you evil?
Saline: ...uhm. That's a trick question. *is flung into the chasm* You're not being fair here!

Priyala
Bridge Keeper: What's y-
Priyala: Priyala. Or so I remember.
Bridge Keeper: *stares* Wha-
Priyala: I want to stop people from being Sued.
Bridge Keeper: HOW ARE YOU DOING THAT?!
Priyala: I can read your mind.
Saline: *from the chasm* F### you, a##hole!
Priyala: *runs over*

And now, for two of my Storyverse characters.

Jack
Bridge Keeper: What's your name?
Jack: Jack. No last name.
Bridge Keeper: What's your quest?
Jack: Quest? Well, I teach computer science, maintain the school computer system and, occasionally, help saving the world.
Bridge Keeper: Wine or beer?
Jack: Nothing. I can't get drunk.

Dacoron
Bridge Keeper: What's your name?
Dacoron: Dacoron.
Bridge Keeper: What's your quest?
Dacoron: I don't have one any more.
Bridge Keeper: Everyone has a quest.
Dacoron: Does my original purpose count?
Bridge Keeper: I'll let that slide.
Dacoron: I was built to commit wartime atrocities.
Bridge Keeper: *stares*
Dacoron: *stares back*
Bridge Keeper: Should we skip the third question?
Dacoron: Yes. *walks on*

Gaspard

Keeper: What is you name?
Gaspard: Gaspard De Grasse.
Keeper: What is your quest?
Gaspard: Right now? Saving up enough money to go to university by working in a high-risk, low pay environment.
Keeper: Terran, zerg, or protoss?
Gaspard: Well, it's all got to do with player preference-- *Is thrown off bridge*
Keeper: *Leans over edge* Fool! Zerg is the only race worth playing!


Angus

Keeper: What is you name?
Angus: M' name is Angus MacFarlane.
Keeper: What is you quest?
Angus: Defending my assigned canon continua!
Keeper: How much do you weigh?
Angus: *Lunges forward, hauls the Keeper off his feet and dangles him over the edge* SAY AGAIN?
Keeper: Nononononononono-- put me down! Put me down! What I meant to say was: what is your daughter's name?
Angus: *Throws the Keeper back onto the bridge* Her name is Sophie. Have a good day. *Walks over to the other side, fuming*


Penny

Keeper: What is you name?
Penny: Penny Chang! What's your name?
Keeper: Doesn't matter! What is you quest?
Penny: Oh, you know, keeping watch the multiverse and stuff. Nothing exciting, really. Hey, what do you do for a living? I mean, you can't stay on this bridge all day long, asking three questions to people who want to cross, right? That's just silly! You've gotta have a house or friends or a life or something.
Keeper: Hey, I ask the questions around here!
Penny: Well, that's just rude. I'm trying to have a polite conversation here! Didn't your parents teach you any manners when you were a child?
Keeper: No. *Is thrown off the bridge*
Penny: What a strange person. *Walks to the other side*


Yakov

Keeper: What is your--
Yakov: *Opens a portal to the other side of the bridge* Sorry, but I don't have time for this, m'ster. Happy hour is in ten minutes at Rudi's!
Keeper: B-but wait!
*Yakov steps into the portal*
Keeper: *Silent for a few seconds* Is this legal?

1. What is your name? John Egbert.
2. What is your quest? Um I don't know yet
3. Are you a homosexual? ...

Keeper: What is your name?
Crowley: A. J. Crowley. Look, have you seen--
Keeper: WHAT is your quest?
Crowley: I'm looking for someone. Have you--
Keeper: HOW fast can an angel fall?
Crowley: ...you threw him off the bridge, didn't you, you--
Keeper: Wrong answer! *tosses Crowley off the bridge*
*Crowley can be heard blessing all the way down, and then--*
Crowley: *muffled* Aziraphale?
Aziraphale: *also muffled* Oh, hello, Crowley. Did you come looking for me?
Crowley: *still muffled* No, I just happened to fall down the same bloody chasm you did.
Aziraphale: *also still mufffled* I see. Thank you, my dear.
Crowley: *still--oh, you know* Don't mention it. Any thoughts on getting out?
Aziraphale: We could fly, I suppose. Only, we'd have to be rather careful not to bounce anyone against the sides--
Crowley: ...angel, have you been having a tea party down here?
Aziraphale: What? Certainly not.
Crowley: ...
Aziraphale: Well, alright, but only a little. They all looked so tired, poor things, so I said, why don't we all have a nice cup of tea? And so we've been talking. It's really rather sad, Crowley, the poor dears have literally been through hell--
Crowley: *groans* Angel, please tell me you haven't been crossing canons again.
Bobby Singer: No, that's definitely not Crowley we know. Since you asked, and all.
Aziraphale: You see? He's really not so bad, I did tell you...
Crowley: Aziraphale, you do realize what these people do, right?
Aziraphale: Of course I do.
Crowley: They hunt demons, angel.
Aziraphale: Yes, well...
Crowley: Sometimes they even hunt angels.
Aziraphale: *shocked* Oh, I'm sure that's not true! You really must stop listening to rumors, dear boy.
Crowley: I didn't have to listen to rumors, I watched their television series--
*this continues for a while. We'll leave them to it, with the brief note that no one gets killed. Or maimed. Or discorporated. And they all got out of the chasm at some point.*

--
Well that...grew. Hope it was enjoyable.

~DF

Boarder!Sergio Turbo

Bridge Keeper: What is your name?
Sergio: Sergio [censored for privacy]
Bridge Keeper: What is your quest?
Sergio Turbo: Currently, finish my school course and get a job. Oh, and obviously writing for the PPC.
Bridge Keeper: Who won the 2012 Formula 1 championship?
Sergio Turbo: ... You want to pick a fight don't you? [insert lenghty rant here about how the Red Bull F1 car was blatantly out of the rules]... and so tell me: you want to know the official champion, or the one who actually would've won it if FIA did its job impartially, AKA the one who morally won it?
Bridge Keeper:...
Sergio Turbo: Your question was ambiguous.
Bridge Keeper: Not again...

Bridge keeper is thrown into the chasm.

I'll do my Agents tomorrow. And yes, I'm a tifoso.
One who backs his affermations with actual proofs, though. (See the blog post I made on the Wiki after the 2012 championship ended. It is pretty much the rant I left out here.)

Let's try, then, precious.

Keeper: What is your name?
Jacques: Agent Jacques Bonnefoy, currently. *looks the Keeper up and down* And you are?
Keeper: ...what is your quest?
Jacques: That's a bit of an odd name, isn't it? Do you get a lot of comments, ...what is your quest??
Keeper: ... *throws Jacques into the chasm*

Reader: Oh, hello. Do you mind if I--?
Keeper: First you must answer three questions!
Reader: ...really? Well, alright. Go ahead.
Keeper: What is your name?
Reader: I go by the Reader right now.
Keeper: What is your quest?
Reader: ...currently, to get to the other side of this bridge.
Keeper: ...Would you ever--
Jacques: Now that was just unfriendly.
Reader: What was?
Jacques: He pushed me into the chasm!
Reader: What?
Keeper: Oh, it's not harmful. I get tossed in there all the--
*the Keeper is tossed into the chasm by Jacques and the Reader* *Jacques and the Reader cross the bridge*
Jacques: So, why did you want to get to the other side of this bridge, anyway?
Reader: ...I have reason to believe that my TARDIS is over there.
Jacques: You 'have reason to believe'?
Reader: Don't ask.
Jacques: ...did you lose your TARDIS?
Reader: *glares* I will throw you into that chasm, Bonnefoy, so help me.
Jacques: Touchy...

Keeper: What is your name?
Dawn: Dawn McKenna.
Keeper: What is your quest?
Dawn: I...don't have one at the moment.
Keeper: ...acceptable. For now.
Dawn: For now?
Keeper: For now!
Dawn: ...oh...
Keeper: What do you do when a man comes at you with a raspberry?
Dawn: Oh, I know this one! Release the tiger.
Keeper: Correct. Go away.
Dawn: Remember to eat your bananas! They're a good source of potassium. *skips across the bridge in an attempted Luna Lovegood imitation*

Keeper: What is your name?
Kozar: I am Kozar.
Keeper: What is your quest?
Kozar: To slay Mary-Sues in battle.
Keeper: Are Daleks supreme at Cluedo?
Kozar: Not anymore.
Keeper: True. You may pass.
*Kozar crosses the bridge*

"What is your name?"
[I don't have one.]
"...what is your quest?"
[To analyze the canonical probability of the speed of an unladen swallow exceeding that of a swallow carrying two coconuts and a Mary Sue.]
"..."
[...]
"Are you sentient?"
[Would you believe me if I said yes?]
"Can you talk?"
[I can flash words on a screen.]
"That doesn't count as talking."
[But you're responding.]
"..."
[Do I get to throw you off the bridge now, or is this only a model?]
*The Keeper runs away*
Edgar's CAD: [The Knights who say Ni triumph again! Ni! Ni! Ni! Bring me a SHRUBBERY!]

--
Hey, anybody can cross, right? :D

~DF

~Scott~

Rookie agent Scott was infinitely frustrated by the bridge keeper, who forced him to answer his little riddle before he could cross the bridge after the fleeing Sue. As his impatience grew, his usually more keen senses began to slip.

"WWWHAT! Is your name?" The bridge keeper demanded.

"Rookie agent Scott, PPC, Department of Bad Crossovers, Assassin's Creed specialist," Scott recited in agitation.

"WWWHAT! Is your quest?" The bridge keeper asked next.

"I'm after that damn Sue you let by, like an idiot!" Scott snarled.

"WWWHAT! Is the color formed by the combination of blue and orange?" The bridge keeper asked one last time.

"I- what? What kind of question is- OHNOOOOOO!!!"

Scott was launched by the force of his incorrect answer into the fiery chasm, abs exploded in a ball of fire against the walls.

~

~Kira~

After having seen his partner get tossed like a table, Kira was on high alert for his questions.

"WWWHAT! Is your name?" The bridge keeper demanded.

"Rookie agent Kira, PPC, Department of Bad Crossovers, Assassin's Creed specialist," Kira answered quickly.

"WWWHAT! Is your quest?" The bridge keeper squawked.

"I'm pursuing a Mary Sure guilty of messing with the canon of Assassin's Creed and Monty Python," Kira replied.

"WWWHAT! Is the temperature where Absolute Zero occurs?" The bridge keeper asked one last time.

"W-what? I'm a PYROMANCER, I don't do low tempera-AAAAAUGH!!!" Kira screamed as he, too, was launched into the chasm. Fittingly, he froze on impact rather than exploding into flames.

~

~Monster Hunter Ethan Darrow ~

Ethan was in no real hurry to cross the bridge. After all, his contract was in a whole other country, and he still had several days of travel to cover before he got there.

"WWWHAT! Is your name?" The bridge keeper asked.

"Ethan Darrow. I hunt big scary monsters," Ethan said with a cheeky grin.

"WWWHAT! Is your quest?" The bridge keeper asked once more.

"See previous answer," Ethan replied. The bridge keeper seemed to accept this.

"WWWHAT! Is the approximate weight of a greatsword?" The bridger keeper asked once more.

"Eastern or Western?" Ethan countered.

"What?"

"Do you mean Eastern, like in Asia, or Western, like in France?" Ethan asked.

"...Well, you see, uh, I was just- GAAAAAH!!!"

The bridge keeper was launched by the force of his own folly into the chasm he guarded, and exploded in a ball of flames. Meanwhile, Ethan whistled happily as he casually crossed the bridge.

Eledhwen
Keeper: What is your name?
Eledhwen: Do you mean the name given at my birth, the name chosen with the foresight of my mother, the name I was given after a certain event that had to do with stars, or the name I hid under while fleeing from a Mary Sue Factory?
Keeper: ...
Eledhwen: It is so dreadfully ambiguous.
Keeper: Oh, bugger. (thrown into chasm)
Eledhwen: (crosses) At least he did not ask this question of Aragorn or Túrin Turambar.

Christianne
Keeper: What is your name?
Christianne: Christianne Marian Shieh.
Keeper: What is your quest?
Christianne: To protect the Multiverse from Suvians.
Keeper: What do you get when you cross a seagull with an octopus?
Christianne: ...A feathery mop that says 'mine' constantly?
Keeper: The correct answer is 'Squawktopus'...
Christianne: {takes out a gun)
Keeper: (hastily) But you did describe the thing, so I suppose you pass.
Christianne: Good! (skips off to join Eledhwen)

The Disentangler
Keeper: What is your name?
Dis: My name is lost in the mists of time, in the heart of the Medusa Cascade - wait, no, that's the Doctor. I'm the Disentangler, or Lachesis, or this convoluted Gallifreyan name that would take me a good five minutes to say.
Keeper: What is your quest?
Dis: To explore strange new worlds, to seek out new life and new civilsations, to boldly go where no Time Lord has gone before - crap! No, that's the Enterprise -
(The Disentangler is thrown into the chasm)

The Agent
Keeper: What is your name?
Agent: The Agent.
Keeper: What is your quest?
Agent: To make sure my partner does not get herself killed... again...
Keeper: How do you make a soufflé?
Agent: A soufflé isn't a soufflé; a soufflé is the recipe.
Keeper: ...fair enough.
Agent: (passes)

The Fisherman

Bridge Keeper: What is your name?
Fish: That doesn't have as straight an answer for me as it would for most people. Regardless, I'm called the Fisherman.
Bridge Keeper: What is your quest?
Fish: Defending the multiverse. From... well just about everything it seems. Oh, and trying not to get killed along the way.
Bridge Keeper: If I wanted to fit three 64-dimensional entities inside a 4D Sienna-Volsky trap, how much energy would I require?
(The Fisherman's eyes go wide for a moment. He starts babbling, frantically trying to calculate in his head. He picks up a stick.)
Fish: Mind if I do some working out? Go on, ask her the questions, come back to me.

(The Keeper nods, and the Fisherman begins scratching formulae into the dirt.)

Evie
Bridge Keeper: What is your name?
Evie: As the person who rescued me had absolutely no imagination or sense of shame, it is Evie. Encapsulated Virtual Intelligence Entity.
Bridge Keeper: What is your quest?
Evie: What he said. With the added burden of stopping him from practicing his hobby of 'doing the most insane thing possible'. Which is harder than it looks, believe me!
Bridge Keeper: Twilight or Mortal Instruments?
Evie: Oh for the love of... fine. Mortal Instruments. Only because I've been to the Twilight continuum and seen how bad it is. Maybe MI isn't so bad.

(Evie is allowed to cross. The Fisherman suddenly stops his calculation and stands up.)

The Fisherman, cont.

Bridge Keeper: Do you have an answer?
Fish: Do you?
Bridge Keeper: I do not understand.
Fish: You said "If you wanted to fit three 64-dimensional entities...". Well? Do you?
Bridge Keeper: That is not the question.
Fish: Logically, there were two questions in your response. That is ambiguous without clarification. So, unless you feel like taking a swim, shall we just forget this whole thing?
(The Bridge Keeper looks at the chasm behind him, and then nods. The Fisherman smiles and runs to catch up with Evie.)

Evie: What's a Sienna-Volsky trap?
Fish: No idea. Don't even think it exists. Why are we here? What is here anyway?

...To bad I don't have any okayed agents yet. Drat.

Cyba

Bridge Keeper: What is your name?
Cyba: Cyba Zero.
Bridge Keeper: What is your quest?
Cyba: To rid the multiverse of bad spelling, bad punctuation and bad grammar!
Bridge Keeper: What is your favourite colour?
Cyba: Red!
(Cyba crosses the bridge without incident.)

Sigma

Bridge Keeper: What is your name?
Sigma: Sigma One.
Bridge Keeper: What is your quest?
Sigma: Perfection... (She clamps her hands to her throat.) Er, I mean to make my ship look nice!
Bridge Keeper: First answer only!
Sigma: AAAaarg...huh? (She is surprised not to go flying into the chasm.)
Bridge Keeper: What were the names of the first two PPC agents?
Sigma: Jay and Acacia. (She starts towards the bridge.)
Eagrus: Wait... you mean perfection was the right answer?
Bridge Keeper: Yes.
Eagrus: SIGMA!!!!
Sigma: (She legs it across the bridge as fast as she can.)

Eagrus

Bridge Keeper: What is your name?
Eagrus: Eagrus Khan.
Bridge Keeper: What is your quest?
Eagrus: To learn magic and rid the world of bad spelling... but only after I remind Sigma to ignore her tendencies!
Bridge Keeper: What colour is your hair?
Eagrus: (Glares.) Wilver. (He runs after Sigma.)
(Two sets of snickering can be heard from somewhere in the mist, but they stop abruptly as Eagrus arrives and starts lecturing.)

Phi

Bridge Keeper: What is your name?
Phi: Phi Six.
Bridge Keeper: What is your quest?
Phi: To discover a cure for Stu-ness.
Bridge Keeper: Which is better, magic or tech?
Phi: Tech, OBVIOUSLY!
Eagrus: (from somewhere in the mist) NO IT ISN'T! MAGIC IS ALWAYS BETTER!
Phi: (dashes across the bridge) TECH!

(The magic versus tech debate continues to be audible for quite some time.)