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The entertainment value comes from three layers:

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In the world of comedy, few scenarios are as ripe for slapstick and awkward humor as the "fish out of water" trope. When you combine that with the slightly risqué, yet comical nature of 20th-century lingerie marketing, you get a subgenre of comedy that holds a distinct place in pop culture history. The entertainment value comes from three layers: Here

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The phrase "the lingerie salesman's worst nightmare" refers to a specific viral video and internet meme involving a person wearing an elaborate, often absurd or "cursed" outfit that humorously defies the expectations of a traditional lingerie setting. Origin and Context