This is a subversion of Popcultural Osmosis. When used in-universe, it's usually as a means of showing the difference between people from two different groups (usually generations) in which a character from Group A makes a pop culture reference (or mentions a famous person or movie or work) and one of four things happens:
"Who's X?" — The person from Group B doesn't get it at all because of a failure of Popcultural Osmosis. This seems to be the most common.
"Oh, X! He was in Y, right!" — The person from Group B gets it wrong because of a failure of Popcultural Osmosis (and he's guessing).
Agent 355 from Y The Last Man never gets pop culture references; at the end, when Yorick brings up Moonlighting he explains what it is "before you ask". In the Distant Finale, set 60 years after the rest of the story, when Yorick asks his young clone, if he knew that Elvishad a twin brother, he asks: "Who's Elvis?"
Using in-universe media, Transmetropolitan sees this happen to Spider Jerusalem. When a band comes up on the TV, he mentions an earlier musician that did the same genre better, then asks Channon if she's heard them:
Little Rock: Who’s Bill Murray? Tallahassee: Alright, I’ve never hit a kid before. I mean that’s like asking who Gandhi is. Little Rock: Who’s Gandhi?
Also done in reverse with a hilarious scene where Little Rock is trying to explain the concept of Hannah Montana to Tallahassee, which crosses into Real Life, as that scene was, in fact, the two actors just talking as they left the camera running.
In Sister Act 2, Delores wants to hear her students sing, so she singles them out and has them sing "Mary Had a Little Lamb". One girl doesn't know it. Yet oddly enough, she does know the theme from The Love Boat. This is truth in television for a lot of first and second generation immigrants.)
Live Free Or Die Hard: Generational differences are a major theme in this belated sequel, and so variations of this come up frequently. For instance, Justin Long's character fails to understand what "Fortunate Son" by Creedence Clearwater Revival is — to him, it's noise. (The writers and McClane are hit with Isnt It Ironic here, but oh well...)
William: Is this your first film? Actress: Well... actually, it's my 22nd! William: Any favorites among the 22? Actress: Working with Leonardo. William: DaVinci? Actress: DiCaprio. William: Of course. And is... is he your favorite Italian director?
In How Do You Know, George tells Lisa how his mother left his father after watching Kramer Vs Kramer, but she's never seen the movie, and doesn't get why his story was supposed to make her see him in a different light.
Occurs in Jolly Roger: Massacre at Cutter's Cove when a character brings up Dirty Harry ("Dirty who?")
Ridzik: Captain Danko, congratulations. You are now the proud owner of the most powerful handgun in the world. Danko: Soviet Podbyrin, 9.2 millimeter, is world's most powerful handgun. Ridzik: Oh, come on, everybody knows the .44 Magnum is the big boy on the block. Why do you think Dirty Harry uses it? Danko: Who is Dirty Harry?
Lori: Is that my ringtone? What is that? Cause it sounds negative. John: No. I-it's from The Notebook.
Denis Domaschke in Goodbye Lenin is a West Berlin amateur filmmaker showing off his talent to Alex Kerner, his East Berliner co-worker just after the fall of the Berlin Wall. He displays a wedding video he made referencing 2001ASpaceOddity - which Alex has never seen or heard of due to cultural isolation.
The World Of Henry Orient is about two young teenage girls, Valerie and Marian, who develop a crush on concert pianist Henry Orient. Valerie's mother finds out and gets Valerie into trouble, which Marian doesn't appreciate. Boothy brings up her own childhood crush on John Barrymore, and Marian asks, "Who's he?"
Barclay grunts softly. "War of the Worlds." Gould blinks. "Huh?" "Nineteenth-century novel," Barclay says.
In a Scrubs episode, the Janitor tells Eliot that he changed the address in his personel file to "1 Cemetery Lane" because Dr. Kelso keeps calling him "Lurch". Eliot just looks at him in polite incomprehension.
Shirley: You remind me of Sam and Diane... I hated Sam and Diane. Anne: Who are Sam and Diane? Shirley:(furious) Okay, I get it! You're young!
Another example is when they are suggesting Abed change his personality:
Abed: You're gonna Can't Buy Me Love me. You know, transform me from Zero to Hero, Geek To Chic? Troy:Ohhhhh, he wants us to Love Don't Cost a Thing him. Shirley: Ohhh! Troy:Cant Buy Me Love was the remake for white audiences. Shirley: That's so uncomfortable when they do that, I can't believe they didn't insult anyone.
Temperance "Bones" Brennan's Catch Phrase for virtually any Pop Culture reference: "I don't know what that means." (She notably did know who Stewie was when it came up.) She is sliding from Type 1 to Type 2, albeit slowly. In one episode, she tries to console Sweets (who's just broken up with his girlfriend) by offering to take him to the "bowling rink"....
Sawyer constantly uses pop-culture references in his sarcastic quips and derisive nicknames. This backfires when he calls another character "Bobby", and specifies that he's referring to The Brady Bunch, only to get the response "What the hell is The Brady Bunch?" This exchange implies that the character grew up on the island and has little knowledge of the outside world.
Sawyer himself fell victim to this in a Season 6 episode where Hurley mentioned Anakin, prompting a response of "Who the hell is Anakin?".
Sam on Quantum Leap occasionally fails to get Al's pop-culture references, such as in "Glitter Rock," when he doesn't know who Pete Townshend is, leading to a Who's on First? exchange. This is mostly due to time-travel-related memory loss, although (as in this example) it might occasionally occur just because Sam is a huge nerd.
The scene in Angel (which, not by chance, is similar to the Captain America example, above) where the green-skinned demon Host of Caritas reveals that his actual name is Lorne:
Lorne: Though I generally don't go by that because — Green. (points to his face) Cordelia: Huh? Angel:(smiles) Right. Lorne Greene. (Cordelia and Wesley stare at him)Bonanza? Fifteen years on the air not mean anything to anyone here? Okay, now I feel old.
Holtz is warned about this when he's brought forward in time to the present day. He takes any strange references in stride:
Recruit: So, what, you're going to go all Mr. Miyagi on me?
Holtz: You will find that your modern pop culture references are lost on me.
Giles is unaware of Spider-Man or Jimmy Olsen. Spider-Man came out in America in 1962, when Giles would have been about 8, if we go by Anthony Head's age. Giles has likely heard of Spider-Man and Superman, but doesn't know any details about them. He never gave any indication that he read comic books/watched American cartoons as a kid, so there's no reason to suppose he's lying just to maintain his image as Stuffy British Man. (There's definitely reason to suppose he's lying about never having done magic prior to becoming Buffy's Watcher...)
Apparently, Reid's never heard of the sitting in a tree song. He's also completely unaware of Twilight.
And then there's this:
Rossi: This from someone whose favorite album is The Beatles' White Album. Hotch: Just because Manson liked it doesn't mean that it has to be ruined for the rest of us. Reid: That's why I stick to Beethoven. No chance of negative associations. (beat) JJ: ... really? You've never heard of a movie called A Clockwork Orange?
Hilariously subverted by Rossi, who knows Niko Bellic is a character from Grand Theft Auto.
Sheldon will often not get references of popular subjects he deems to be beneath him.
Sheldon: I know everything about the universe. Penny: What is Radiohead? Sheldon:(pause) I know everything important about the universe.
In the All In The Family episode "Archie and the Computer", Mike complains about the increasing role of computers in society:
Mike: Pretty soon, we're not gonna be names, just numbers! It's Nineteen Eighty Four! Archie: Eh, shut up, you don't even know what year is!
In the Doctor Who episode "The Empty Child", Rose jokingly refers to the Doctor as "Mr. Spock". Jack, who's from the future, doesn't get the reference and assumes it's actually the Doctor's name.
Happens a lot in Star Trek due to the various alien races interacting with a mostly human main cast. The largest examples are Data's various failures in Star Trek: The Next Generation and Kira being frustrated several times by Sisko's references to baseball and never having heard of Captain Kirk in Star Trek: Deep Space Nine.
In the episode "Bad Guys", Cameron compares someone to John McClane. Daniel doesn't understand. Teal'c, who is not even from Earth, explains, Die Hard.
Vala also regularly complains about her teammates using Tau'ri pop culture references, which she never get.
Comes up twice in Stargate Atlantis, both time involving Neil De Grasse Tyson and Dr. Keller. First, in "Trio", Colonel Carter uses Brian Greene and Neil De Grasse Tyson in a game of "Who would you rather?", explaining to Keller that she chose physicists who were on TV so Keller should know them (she doesn't.) A season later, in "Brain Storm", Tyson introduces himself to Keller and adds "from television" when she seems confused.
In one episode of How I Met Your Mother, Robin mentioned several canadian celebrities in a row, none of which her friends knew about.
Barney: What's the opposite of name dropping?
In the Seinfeld episode "The Stranded" Elaine quotes the line "Maybe the dingo ate your baby?" from A Cry in the Dark. The woman she's saying it to doesn't get the reference.
Monk: In "Mr. Monk and the Foreign Man", the African visitor compares a situation in a laundromat to Friends. Monk assumes that it is an African TV program.
Also, in "Mr. Monk Gets Lotto Fever," Natalie tries to teach Monk that their friendship is comparable to Simon and Art Garfunkel, to no avail as Monk is unfamiliar with the duo, mistaking Garfunkfel for Garfield and for a carbuncle.
Castle: In "Last Call," the eponymous character is quite disappointed when nobody gets his Jaws reference:
Lanie: Classic indicators point to deliberate blunt force, so I’d say no. This was no boating accident.
Castle: Then we'd better close the beaches.
[Beckett and Lanie stare at him blankly]
Castle: No boating accident? Chief Brody? Hooper?
[They still don't get it]
A bit character in NCIS thought one of his employees was childish for being into video games; said employee apparently ran a Skyrim message board in his spare time. After he insults McGee by assuming (correctly) that he's into dweeby role-playing games, McGee responds, "I used to, but then I took an arrow to the knee." The guy looks confused and glances at McGee's legs.
In the Weezer song "El Scorcho", the singer sees this as another attractive trait of the girl he's wooing: "I asked you to go to the Green Day concert. You said you'd never heard of them. How cool is that?"
Whateley Universe: Phase, being a Fish out of Water, often fails to get the anime and cartoon jokes that his teammates make (he has had to sneal away and search for the reference on the internet), while his teammates sometimes don't get his jokes (because classical lit jokes go over so well with high schoolers).
In Screwattack's review of the 16-bit adaptation of Judge Dredd, Stuttering Craig claimed he'd never heard of the original comic and was going by the movie.
This page of Gunnerkrigg Court, where it indicates that Annie barely knows anything about pop culture because (as we learn elsewhere) she grew up in a hospital.
Kat: Welllll, he's not perfect! I mean, he thinks The Prodigy's Fat of the Land is better than Music for the Jilted Generation. (Antimony thinks about this for a panel) Antimony: I have no idea what you just said.
Antimony is similarly confused when Kat refers to "the Princess Mononoke look you got going on!"
The comic El Goonish Shive had this happen with Grace when confronted with a Santa look-alike. Of course, this is someone who was cut off enough from society to ask the question "World War Two?! How many have we had!?"
Raven: Have you considered Mount Doom? I'm sure we could rustle up some sacrificial hobbits... Abraham: I... What? Raven: Mount Doom? A fictional volcano? How dare you survive to this age and not get that reference.
And again, same story:
Damien: Who are you?
Elliot: Tell me your name, horse master, and I will tell you mine.
Later in the series, Omi will frequently attempt to make a pop culture reference or use a common figure of speech but badly misword it, prompting another character to correct him, only for Omi to misinterpret the actual reference.
Omi:(taunting the villain) Defeating you will be a piece of pie. Clay: Cake, you mean a piece of cake. Omi: Cake? This is no time for food.
In one instance, Omi miswords one of his attempted references so badly that none of the other characters can figure out what he was actually trying to say.
In Family Guy Brian once took Frank Sinatra, Jr. out club hopping, where his attempts to flirt with one vapid young woman fall completely flat because she doesn't recognize any of the names Sinatra keeps dropping. Brian has intervene and stop the increasingly frustrated Sinatra from backhanding the girl.
Brian himself had this happen when he attempted to hit on another vapid girl, mentioning that he's an author. It falls flat as the girl appears to have no idea what books are, leading Brian to resorts to explaining it's like an iPad made out of paper.
In American Dad, Stan's repeated bafflement at things Steve mentions probably is the reason they haven't bonded well. Notably, during a father-son road trip when Stan needed a door to complete the DeLorean he was restoring, he's continuously annoyed and confused when Steve drops references to Back to the Future, which he claims to have never heard of.
In The Simpsons 2011 episode; when Cheech and Chong are making a reunion tour — ironic considering The Simpsons ran throughout the 90s, but Comic Book Time may apply:
Bart: Who the hell are Cheech and Chong? Homer: Cheech and Chong were the Beavis and Butt-Head of their day! Bart: Who are Beavis and Butt-Head?
A.J.: Have you ever heard of Evel Knievel? Lev: No, I never saw Star Wars.
Live Free Or Die Hard: When John McClane finally gets to "Warlord"'s place, his reluctant ally tries to pass him off as another of the culture, which fails fast. Notable is when McClane fails to recognize a cutout of Boba Fett and tries to cover it by saying he's only familiar with Star Wars. (McClane's smirk seems to suggest he's just screwing with "The Warlord" with that one.)
In Waxwork, one of the young people asks if the Phantom of the Opera figure's mask is the original from the movie, and the owner is surprised that someone made a movie about the Phantom. It's implied that the owner is not merely pop-culture clueless, but that he knows the Phantom actually existed in the movie's Verse and is amazed Hollywood would resort to filming his tale.
For those who are unfamiliar with these artists (due to age, musical taste, or geography), they have similar artistic styles, but Springsteen is much more famous around the world, and particularly in the US.
In its episode guide to Lois And Clark, SFX magazine explains that Perry's anonymous source Sore Throat (who actually refers to the line "Follow the money" at one point), is a parody of Deep Throat ... from The X-Files.
Basically the reason Covered Up and Sampled Up exist (just see the opening quote for the former entry).
In Linkara and Spoony's crossover review of "Warrior #1", Spoony mocks the Ultimate Warrior's disjointed speech patterns by quoting Col. Campbell's infamous line from Metal Gear Solid 2 near verbatim (only adding a "Hoak Hogan" to keep with the theme). Months afterward, TGWTG fans who apparently never played MGS2 would often spout "I need scissors! 61!" when talking about the Ultimate Warrior, as if believing the line only came from that review.
In "The David Bowie Drinking Game" (which, true to its name, is loaded with David Bowie shout outs), Spike says that Rarity was kidnapped by "scary monsters and super creeps!" Twilight corrects him: "It's scary monstersand nice sprites!" Everyone else is aghast at Twilight's ignorance, and at the episode's end Twilight admits that she has no idea who Bowie is.
In "The Longest Episode", Pinkie shares her The Lord of the RingsSelf Insert Fic, and her audience tells her that she's ruining a classic book. Pinkie is shocked to realize that "There's a book of Lord of the Rings?"
In a Robin annual, Huntress tells Robin it was a clever idea of his to wear mirrors under their ponchos (to blind their enemies in a gunfight). He says he got the idea from an old movie. She says "A Fistful Of Dollars, huh?" and he replies "No. Back to the Future III."note It might make you want to Headdesk when you realize Marty got the idea from seeing that very scene from A Fistful of Dollars in Back to the Future Part II, and that Marty had identified himself as Clint Eastwood upon arriving in 1885.