The sentence with the most prepositions at its end -- does it really work?

What did you bring that book that I don't want to be read to from out of about 'Down Under' up for?

I was wondering whether this sentence is actually correct and if it is, whether someone could explain which preposition points to what in that sentence.

Solution 1:

It's technically (almost) correct, but obviously a pathological case for the fun of it. Moving the prepositions into their "standard" positions and adding the appropriate pronouns gives:

For what [reason] did you bring that book about 'Down Under', out of which I don't want you to read to me, up [here]?

That is, from back to front:

• for refers to what (what for = why)
• up refers to bring (bring that book up)
• about refers to Down Under, which is just a title
• out of or from (but not both) refer to that book (out of that book)
• to refers to the speaker (read to me)

The from out of bit is incorrect, as you can tell if you try to rearrange the sentence to involve both from and out of: it should be either from (the book) or out of (the book).

Though you should usually avoid doing so excessively, it's perfectly correct in many cases to shift a preposition to the end of a clause and omit the pronoun (such as which or whom) that would otherwise be involved:

To whom are you talking?
Who(m) are you talking to?

There's a long history of prescriptivist grammarians considering it incorrect to end a clause with a preposition, but there's such massive precedent in favour of doing so, and it's so common in ordinary speech, that you can't legitimately make the claim that it's outright wrong. And for certain examples, as the above, it sounds so awkward and stilted to use the “correct” form that that form cannot possibly be the truly correct one.

Solution 2:

The "for" in the end refers to "What" at the beginning of the question.

"What for?" means "For what reason?" or "for what purpose?", so you could say the question this way as well:

For what reason did you bring that book...

You bought another hat? What for? You already have lots.

About the question being correct... It's too complex for me (I'm not a native speaker) but even if it's correct, it's written in a very complex way, it's not really clear.

Solution 3:

The sentence actually breaks a couple of common patterns in English that have nothing to do with preposition stranding.

Firstly, in English (but not all languages), speakers tend to postpose relative clauses even though that means the relative clause doesn't surface right next to the element it modifies. So in a case like this:

(a) John bought the cups that Daniel had been looking for for him.

(b) John bought the cups for Daniel that he had been looking for.

word order (b) is more natural. This isn't really to do with the postposed preposition: if you substitute "had been wanting", (b) is still generally the more common/natural word order.

Then, perhaps conversely, in so-called "picture" expressions ("a photo of Jane", "a book on flower arranging", "an impression of disgust", where you can't say "*a flower arranging's book", "*a disgust's impression" etc), it seems a bit more usual to keep this expression together. So it is odd to separate "about 'Down Under'" from "book" in this way, even ignoring the other syntactic features of this sentence.

Whilst neither of these patterns is a 'hard and fast rule', they're two unusual features of syntax which the sentence has.

Or in other words, the unusualness of this sentence isn't per se to do with the postposed prepositions.