Bob is trying to tell a story or joke, or ask a hypothetical or rhetorical question. He's interrupted constantly by requests for unnecessary extraneous details, quickly derailing the story into a "Shaggy Dog" Story or a Metaphorgotten. Common culprits are the Constantly Curious, the missing-the-point Cloudcuckoolander or the Mouthy Kid who's just trying to get on his nerves. A Bad Liar or someone who Cannot Tell a Joke may do this to themselves, adding unnecessary detail or going back and changing things.
Compare Derailed Fairy Tale, where the listener insists on adding his own details in; Sidetracked by the Analogy, where a listener focuses on the irrelevant details of an analogy; and Distracting Disambiguation, where they interrupt to needlessly clarify terminology.
If the speaker is sidetracking himself, it might be a case of Disorganized Outline Speech, where he doesn't really know what point he's trying to make in the first place, or Metaphorgotten, where unnecessary deviation sends an analogy off track.
- In Seitokai no Ichizon, a rather basic math problem gets derailed in this way.
- In the Disney Channel Original Movie Pixel Perfect, the computerized character interrupts her creator's description of what falling in love feels like with questions like this.
- In Monty Python's Life of Brian, telling the Parable of the Talents (Matthew 25):
Brian: There was this man, and he had two servants.
Arthur: What were they called?
Arthur: What were their names?
Brian: I don't know. And he gave them some talents.
Eddie: You don't know?!
Brian: Well, it doesn't matter!
Arthur: He doesn't know what they were called!
Brian: Oh, they were called 'Simon' and 'Adrian'. Now?
Arthur: Oh! You said you didn't know!
Brian: It really doesn't matter. The point is there were these two servants?
Arthur: He's making it up as he goes along!
- In fact, the Pythons loved this kind of gag. Just in the Dennis Moore sketch John Cleese got lost in discussions about his target practice, British botany, European history, human anatomy and Not Actually the Ultimate Question while trying to rob some nobles.
- In the famous opening scene of Monty Python and the Holy Grail, King Arthur's attempt to summon the Lord of the local castle derails into a discussion of how exactly King Arthur acquired a coconut shell in Medieval England, and ends with an argument over the migratory patterns of swallows.
- Also from the Pythons, or at least Michael Palin, John Cleese, and Graham Chapman, comes How To Irritate People. In the show, which is a collection of sketches like Monty Python's Flying Circus, a man tries to tell his employer, who is visiting for tea, a joke he heard. Actually his wife wants him to tell it, and she keeps interrupting him to input unimportant details.
- Subverted in Phenomenon. Somebody asks John Travolta's character how old a person would be now if they were born on the 5th of March 1987 (or was it the 7th of July 1976? No, it was the 28th of October 1928...) Anyway, he asks a bunch of questions, the last one being "Where was he born?" The exasperated questioner asks what that has to do with it. "Well, if he were born in New York City he'd be..." and gives the age right down to the minute. He never does explain, though, how a person's gender affects their age.
- In Blade Runner, Holden asks Leon to imagine a hypothetical situation where he's walking in the desert and finds a tortoise on its back, the idea being to evoke an emotional response in order to determine if Leon is really human. Leon misses the point entirely (or, it is strongly implied, PRETENDS to miss it) and wants to know which desert, why he's there, etc.
- In Stand by Me, Vern likes Gordy's story about Lard-Ass but isn't quite happy until he knows whether there was an entry fee for the pie-eating contest.
- In Pirates of the Caribbean: The Curse of the Black Pearl, Jack Sparrow manages to hijack a ship by leading guards Mullroy and Murtogg to one such conversation.
- In Take the Money and Run, we see an interview with someone who saw something related to to the protagonist, a career criminal. The interview subject mentions he was drinking juice, and gets distracted trying to remember what kind of juice it was.
- In Saki's short story The Story-Teller, the story-teller is so successful with the children because of his ability to readily answer their irrelevant questions and incorporate them into the story.
- In his "Corfu Trilogy", Gerald Durrell relates that this was the only way he was able to learn history. His tutor told him all about Lord Nelson's butterfly collection and the names of Hannibal's elephants.
- In one of his stories, Ephraim Kishon tries to tell a joke to a Swiss gentleman, who then uses this trope. The dialogue ends like this:
Kishon: It doesn't matter which tunnel! For all I care, it could be the Schlesinger tunnel!
Swiss: The Schlesinger tunnel? Now that's funny! Ha-ha-ha...
- At the end, Kishon is so frustrated and ashamed, he hangs himself with an indestructible Swiss tie.
- This is the reason C. S. Lewis gives for doing a flashback to narrate the story of Prince Caspian. He says that if he showed the story through Trumpkin (the last chapter ended with Trumpkin saying he'll tell the children what had happened) it would take longer as he'd have to stop for all the interruptions. So he takes over for the time being, and then the next chapter begins with the children reacting to the finished story.
- Sherlock Holmes has a tendency to appear to do this, such as in The Adventure of the Blanched Soldier, where he interrupts a story to ask about the newspaper someone was reading. However, being Holmes, everything is a means to an end and an important detail in solving the case.
- A frequent occurrence on the Discworld. Samuel Vimes lampshades it in Guards! Guards! by saying that if a god showed up in Ankh-Morpork saying "let there be light," he'd get no further because of all the people saying "what color?" Of course, Vimes is frequently guilty of this himself in future books.
- The Abbott and Costello sketch Jonah and the Whale: Lou's trying to impress a pretty girl with a joke, but Bud keeps interrupting with demands for details.
- On The Wire, Prez tries to set his class a Train Problem and they pester him for pointless details (which side of the city this guy is from, what the purpose of the trip is, etc.), distracting from the basic maths problem he was trying to get across.
- On The Office (US), when asked which five books he would want on a deserted island, Dwight is obviously thinking too hard about it and asks whether there is any firewood on the island or whether he lost his shoes before he got there.
- Dwight loves this trope — when asked whether it is just for a man to steal a loaf of bread to feed his family, Dwight just adds his own details — the bread is poisoned, and the kids aren't even his.
Stephen Fry: What I want you to do first is tell me all about the twelve Frenchmen and the twelve mosquitoes. Dara?
Dara Ó Briain: Once upon a time... there were twelve Frenchmen, called 'Appy, Sleepy, Arrogant, Furieux, Choses comme ça, Bof, and Zut Alors. And...
Phill Jupitus: That's six!
Dara: Fenêtre... er, Boulangerie, er...
Alan Davis: Le Table!
Dara: La Table, of course, and Jambon et Fromage, the twins. And they used to travel around with mosquitoes, solving adventures.
Phill: And what were the mosquitoes called?
- In How I Met Your Mother, when Ted wakes up with a strange girl in his bed and a pineapple on his nightstand everyone tries to figure out who the girl is and how Ted hooked up with her ... except for Marshall, who's fixated on getting details about the pineapple. And they never do figure out what the hell the pineapple had to do with anything.note
- In Friends, Joey tells Ross a story about France which he swears is a guaranteed pass at getting laid. When Ross tries to repeat the story to a woman, it quickly devolves into this, just because she's genuinely curious about his time in Europe and he's a Bad Liar.
- In an episode of The Suite Life of Zack and Cody, Maddie is directing a student film with the help of the dim lifeguard, Lance, who plays the role of the wealthy male lead.
Maddie: Okay, Lance, remember: You're rich.
Lance: Rich who?
Maddie: No, I mean you have money.
Lance: So I'm rich, and my name is Rich?
Maddie: No! No, your name isn't Rich!
Lance: What's my name then?
Maddie: It doesn't matter!
Lance: Then why can't it be Rich?
- In an episode of The Suite Life on Deck when Bailey tries to tutor London, we get this exchange:
Bailey: Your bus leaves the station at—
London: (scoffs) I would never take the bus. I would take my private jet.
Bailey: Right...Your private jet leaves the bus station at 6 a.m.
London: 6 a.m.? I would never get up that early!
Bailey: (getting ticked) What time y'think you're gonna get there?
London: I don't know. Ask my chauffeur. He's the one driving me.
Bailey: (really ticked now) So let's assume that your chauffeur has gotten you to your private jet at say, noon.
Bailey: You'l have lunch on the plane!!
London: (claps) Goodie!! Wait, what are we having?
- In an episode of The Suite Life on Deck when Bailey tries to tutor London, we get this exchange:
- This was Mr. Kimball's schtick on Green Acres. He would constantly interrupt himself to make corrections or qualifications, both unnecessarily pedantic and complete 180-degree retractions.
- An episode of Stargate Atlantis had Mckay trying to ask the team a hypothetical question that involved whether they would be willing to stop a train that was going to hit a group of ten people by redirecting it so it killed a baby. The thought is quickly lost as the team question why the people wouldn't simply save themselves and whether they could outrun the train.
- In Scrubs, Carla tries to use a metaphor to explain why they should help Elliot. It does not go well.
- Carla: If J.D. were drowning and he told you he didn't want you to save him, wouldn't you do it?
Turk: That depends. What if there're hot chicks at the pool? Maybe he wants one of them to jump in and save him?
Carla: Let's say there's no women.
Turk: There's always women at the pool, baby!
Carla: Fine. He's in a pond.
J.D.: Oh, I would never swim in a pond! They're infamous for serpents!
Turk: You could swim at the Y on Tuesdays — men only.
J.D.: Have you been to the Y on Man Night? Not me.
Carla: N — oka — fine! Turk's the one who's drowning!
Turk: Oh! So now a brother can't swim!
- Israeli skit show Domino featured a skit in which a scout leader tries to tell a group of girl scouts a fairy tale, only to be bombarded with questions like these. It gets to the point she mentions a bear showing up, and one of the girls asks how old the bear is.
- In an episode of Frasier, Martin ends up doing this to himself. Frasier and Niles are trying to write a book about sibling rivalry but are stuck for ideas, and hit on the idea of using examples from their own personal history to start off. They ask Martin for some, and he remembers a really funny story about a time the family took a vacation to a summer house near a lake... but, much to Niles and Frasier's frustration, gets hung up on trying to remember what the lake was called, to the point where he wanders off without actually telling the story so he can look it up.
(Frasier, Roz, and Martin hear the doorbell buzz)
- Frasier and Roz are convinced that the Barracuda will be stopping by Maris' suite for an evening of passion; however, Martin is not up to speed on the latest turn of events:
Roz: It's the Barracuda!
Martin: Who's the Barracuda?
Roz: He's a sleazy Latin lounge singer Maris is going to sleep with to get back at Niles for kissing Mimi!
Martin: Who's Mimi?
Frasier: A horny society boozer and the Mrs. O'Leary's cow of our current predicament!
Martin: Who's Mrs. O'Leary?
Frasier: A woman in Chicago who— oh, I don't have the time!
- On Ricky Gervais's XFM show, Karl Pilkington's stories were very prone to this. It was an especial problem when it came to his "Rockbusters" clues, which Ricky would often interrupt to warn listeners that whatever detail Karl was trying to settle to his own satisfaction might be completely irrelevant to the actual answer.
- Played with in a That Mitchell and Webb Sound sketch revolving around one man trying to tell another man a brain teaser; the reason the second man keeps requiring constant clarifications is partly this trope, and partly because the brain teaser is a bizarre combination of Knights and Knaves, the Monty Hall Problem and the Fox-Chicken-Grain Puzzle.
- In South Park: The Stick of Truth, when the protagonists finally face off against Clyde, they try to tell him that the mysterious green goop he's been using isn't Taco Bell green sauce, which eventually leads into a discussion about how Taco Bell now have the green sauce in packets.
- The story as written in the instruction manual for Cubivore was written in this manner. For example, the story begins by saying the game takes place in "a certain place", and a second party asks where exactly. This prompts the narrator to restart the story, this time insisting he doesn't know where the game takes place.
- In El Goonish Shive, the villain currently known as "Not-Tengu" tries to explain that "Tengu" is just his screen name and is on the verge of revealing his true name when Nanase and Charlotte question and comment on how he looks almost nothing like the actual mythological creature.
- As a meta example, a lot of serial webcomics have this happen to the stories themselves. A creator will post a page, and there will be tons and tons of questions and comments and speculation and possible plot-hole pontificating, which the author will then have to spend at least half of the next page providing an answer for. Example: "Why didn't character X do THIS?"; the next update, the characters try that, only to have it fail, or they ask themselves that and come up with an answer. One suspects that comics like The Order of the Stick and Grrl Power would be a lot shorter if the characters didn't have to address every other concern raised by the fans from one page to the next. However, this may also be a good thing, and gives the illusion that the author and characters really did take into account everything, leaving little room for criticism after the fact.
- The Mighty B!: The main character was trying to tell a joke:
"A leprechaun walks into a bar. Wait, you're not supposed to know it's a leprechaun yet..."
- The story gets progressively worse from there.
- In a The Grim Adventures of Billy & Mandy episode, a bookworm (after accidentally possessing Billy's cat) tries to tutor Billy in math, and asks him a classic two-trains question. Billy... makes one of the trains blue, full of clowns named Carl and Larry, with a conductor named Tim who is a vegetarian but secretly sneaks bacon when no one is looking.
- The Simpsons:
- In the episode "Lisa's First Word", an exhausted Marge is trying to get a young Bart to sleep with a typical prince-and-princess story, and has just ended on Happily Ever After. Bart manages to get her to sleep this way, then causes mischief.
- In "Blood Feud", Homer is trying to get Bart to help Mr. Burns unconditionally with his rare blood, as he expects that Burns will give an extravagant gift in return. He tells the "Bible story" of a rich lion who had a thorn stuck in his paw, and nobody could pull it out until Hercules was hired to help. Bart asks how a lion got rich and Homer Hand Waves it as something that could happen in the olden days.
- Played straight in Finding Nemo, to show how uptight and unsociable Marlin is.
Marlin: All right, I know one joke. Um, there's a mollusk, see? And he walks up to a sea,—Well he doesn't walk up, he swims up. Well, actually the mollusk isn't moving. He's in one place, and then the sea cucumber, well they...I mixed up. There was a mollusk and a sea cucumber. None of them were walking, so forget that I—
Bob: SHELDON! Get out of Mr. Johansenn's yard, now!
Marlin: Well, I actually, I do know one that's (chuckles) pretty good. A mollusk swims up to a... No, no, he doesn't swim up, what is he...? He was already there. And a sea cucumber is-is... standing next to him. They don't stand. They grow in one place, but they do lean. Let me start over. There was a sea mollusk and a sea cucumber. And they were both... They were both... Well, they were— They were like friends. No, no, they didn't know each other. 'Cause now, one's gonna ask something that a friend wouldn't know. Um... The sea cucumber looks over to the mollusk. Right? And, he doesn't really look, he sort of glances. Actually, he was in the middle of a sneeze. That's sort of the important thing 'cause you gotta imagine the sea cucumber sneezing. So he sneezes, and then you know the way you do when you sneeze, your head sorta turns accidentally somewhere? So he looks over to the right and he sees the mollusk. And so, he looks at the mollusk and he says, "Hey, not during low tide." (laughs under his breath) Y'know, I didn't get that exactly right. See, let me tell you something: the mark of a really funny fish, the joke doesn't have to go exactly right. It's delivery!
- The film's Visual Commentary presents an extended take on the sea cucumber and mollusk story from an Albert Brooks recording session dated March 2002:
Marlin: So just then, the sea cucumber looks over at the mollusk and says "with fronds like these, who needs anemones?"
- And then averted at the end, after the adventure has taught Marlin to lighten up.
—But what about...