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I'll play your game, you rogue.

I'm on to you, Trebek!

Come on, you nancy boy!

I found these used as some kind of meme. So I googled them but only to have found that those came from SNL Celebrity Jeopardy! which I've never seen once. Could anyone be kind to tell me what are those meaning and why they are funny and when to use them, please?

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According to thefreedictionary, play someone's game means:

To engage or participate in something according to the design, intentions, or constrictions created by someone else

For You rogue, I found this definition from Cambridge dictionary:

a person who behaves badly but who you still like

I'm on to you means:

I'm watching you and I'm aware of what you are doing. (In sense of a threat)

According to thefreedictionary, nancy boy means:

Used as a disparaging term for an effeminate man, especially one who is gay.

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While helen's answer addresses the meanings of some of the particular phrases and idioms, the key to why this is funny is the long-running TV game show Jeopardy!

The SNL skit mimics the format of the game show, and uses the name of the host (Alex Trebek). If I recall correctly, the disruptive player in the skit is pretending to be actor Sean Connery.

The skit is, as far as I can tell, funny because the disruptive player disrespects the play of the game, misinterprets the clues to be crude phrases, and continuously insults the host. This kind of social humor is difficult to explain, especially because I don't get most of it.

The humor is situational and not really a matter of language.

I suggest you do not behave in this way or use these phrases. The phrases are not funny in isolation, and at least "nancy boy" is likely to be offensive.

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You can forget about these phrases. You would never use them.

They're not funny in and of themselves; they're funny because of the absurd contrast between the "rough-and-tumble" character of spy James Bond (as played by actor Sean Connery) in a grotesque caricature of his "lady-killer" ways with all of the charm stripped away, and the mild-mannered character of the host of the Jeopardy TV show, Alex Trebek. That TV show is about trivia, word puzzles, and things of that nature.

  • James Bond is more refined than the "your mother, Trebek" phrases used by the Connery character, I don't think Bond is the connection here. – Deolater Aug 20 '18 at 14:52
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    @Deolater. I don't disagree. It's rather a grotesque caricature of the "lady-killer" aspect of the Bond character in which the refined charm is stripped away. – Tᴚoɯɐuo Aug 20 '18 at 15:27

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