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Bob makes a historical/cultural/pop culture reference and Alice thinks he is referring to something entirely different. Bob corrects Alice but this only leads to another correction, which only confuses Alice again. Bob makes another correction and so on and so on.
Just one mistake and this would just a simple misunderstanding, however string together a chain of these and Hilarity Ensues.
Due to the nature of this trope with multiple cultural references in quick succession, some of the allusions may fly over the audience's head. This usually doesn't actually hurt the comedic potential though.
See Who's on First? for this trope dealing solely with people with unfortunately confusing names.
Abbott and Costello's famous "Who's on First?" comedy routine, where Abbott tries identifying the players of a baseball team to Costello, but Costello's constant misinterpretation of the players' names and nicknames as non-responsive answers leads to Abbott constantly invoking the trope ... and leaving Costello even more confused and frustrated!
In a funny caption post to this image on DeviantArt, Azula from Avatar: The Last Airbender finds herself one cell away from a man who frustrates her and the security guard to no end!
Random other prisoner: "Look on the bright side! You can't send me adware anymore!"
Azula: "That was E-zula, idiot!"
Random: "Nor dress in weird Afro attire!"
Azula: "That's Shaka-Zula!"
Random: "Or dress like a spider!"
Random: "Nor kill Cleopatra..."
Azula: "That was an asp!"
Random: "Nor possess Dana!"
Azula: "Aaargh!!! Slammit!!! That was Zuul!!! I'm in Hell, aren't I?"
Random: "Hmm...just don't become a fill-in for Bruce Wayne, okay?"
Azula (frustrated): "THAT WAS AZRAEL!!!"
Guard: "I don't care if it was Frosty the Freakin' Snowman! Keep quiet in there! I'm trying to play Sudoku down here!"
Random: "Cool! Don't let Sudoku come out of your TV!"
On Fibber McGee and Molly, the character of Mayor LaTrivia was subjected to these practically Once Per Episode. They'd usually involve him innocently using some figure of speech, which Fibber or Molly (or both) would either take too literally or otherwise misinterpret, sometimes on purpose. LaTrivia's subsequent attempts to clear things up would only create more confusion, making him increasingly flustered and confused and generally reducing him to sputtering, incoherent rage by the time his visit was over.
One not involving Mayor LaTrivia, from "Cleaning the Closet":
Fibber: Remember that spring we were up there, and those people were selling flowers on the street corner? Trailing arthritis, I think they were.
Molly: You don't mean trailing arthritis, you mean trailing arbutus.
Fibber: I do not; Arbutus was a guy in Shakespeare. He's the guy who stabbed Caesar in the toga.
Molly: No, that was Brutus.
Fibber: No, you're thinking of that fairy tale: Puss and Brutus.
Molly: No, you that wasn't Puss and Brutus, and what you mean is arbutus.
Fibber: If that's arbutus, what's arthritis?
Molly: Arthritis is when your joints swell.
Fibber: Well, that's what I say. Any place that sells flowers on every street corner is a swell joint.