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The clip below of the Battle of Wits scene from The Princess Bride (IMDB), the character Vizzini (Wallace Shawn) says:

You’ve fell victim to one of the classic blunders! The most famous is never get involved in a land war in Asia, but only slightly less well known is this; never go in against a Sicilian, when death is on the line! Aha ha ha ha… (and then keels over, dead.)

What does the line "never get involved in a land war in Asia" refer to? I don't understand the reference. Does it connect to the plot in some way I'm missing, or is it completely unrelated?

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  • @Jeeped Yes, I'm definitely not planning on doing this, but does the reference have anything to do with the movie's plot, or is it an unrelated reference? – uhoh Sep 28 at 3:17
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    Vizzini is exercising hubris during a 'battle of wits' with the other guy. His megalomania demands that he show his superiority by performing the typical villain monologue. This involves labeling the other guy's actions as a classic blunder. He goes on to describe two other classic blunders. The first is the one mentioned above. The second is 'never go in against a Sicilian, when death is on the line!' Since he falls dead from the poison after saying this, he is proven wrong and the other guy is the better of the two despite Vizzini's high opinion of his former self. – Jeeped Sep 28 at 3:24
  • @Jeeped okay this helps, thanks! – uhoh Sep 28 at 3:33
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Getting involved in a land war in Asia is a classic blunder in the real world. Examples from before The Princess Bride include:

  • The Korean War
  • The Vietnam War
  • The Russian War in Afghanistan

All three were land wars in Asia that have been seen as mistakes. Grave mistakes. Epic blunders. Arguably the most famous classic blunders.

You could also include multiple failed attempts to invade Russia from Europe, the most famous of those being Napoleon’s march into Russia that basically destroyed his once powerful army. Very famous blunder.

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    Thanks, any thoughts on "Does it connect to the plot in some way I'm missing, or is it completely unrelated?" – uhoh Sep 28 at 4:42
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    Hitler made the same blunder centuries later – MissouriSpartan Sep 28 at 11:41
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    @uhoh To me it’s an example of taking down the fourth wall. This land of Florin seems to be not real and not of our time, but long ago. So it doesn’t make sense for Vizzini to know about 19th and 20th century land wars in Asia. Or we could suppose that in the world of The Princess Bride, there is also an Asia and coincidentally all land wars there have been blunders. Mainly I think this line speaks to Vizzini’s character, not to the plot. He’s not only smart, he’s learned in history and politics and war. And of course it’s mainly meant as a joke for the audience. – Todd Wilcox Sep 28 at 21:05
  • @uhoh You could just as well ask about why going in against a Sicilian when death is on the line is a blunder. To me that’s a reference to the Italian mafia, and again we don’t have a lot of good reasons outside of that line to assume there even is a mafia in the world of the movie. That’s also meant as a joke. – Todd Wilcox Sep 28 at 21:09
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    Also, the Grandfather is reading the story to his Grandson. It's possible that he's ad-libbing while telling the story, but they show this as the characters actually saying these things because the Grandson wouldn't get the joke, so in his mind, they actually said them. – user1118321 Sep 29 at 1:07
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"Never fight a land war in Asia" is one of those weird aphorisms that is widely known, but on which nobody agrees who originally said it. It has variously been attributed to Bernard Montgomery (British General), Dwight Eisenhower (American General and later President), and Douglas MacArthur (American General).

The line was in the original book by William Goldman which was published in 1973. At the time, the US was trying to extricate itself from the Vietnam War. Many Americans thought the war a terrible mistake, and "Never fight a land war in Asia" was a frequently heard "obvious truth". A significant fraction of the viewers of the 1987 film would have clear memories of that period of American history.

As @ToddWilcox notes in a comment, the line worked as humor (at least back then) because it brazenly breaks the fourth wall and inserts a highly topical meme from the "real world" into a fairy story where it makes no sense: there is no indication of Asia even existing in the world of The Princess Bride.

As the origins of the quote lapse into obscurity, the humor of it may begin to fail.

  • Thanks for your additional insight! – uhoh Sep 30 at 3:51

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