My answer to the question I posed earlier about five ‘that’s in a row is “The teacher thought that that that that that student used was extraneous.”
What’s interesting about this question isn’t that an English sentence exists with a large number of repeated words in it — “Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo” takes the cake for most surprising sentence in that category — but because of the universality of the rule. In fact, it is possible to construct a grammatically-valid sentence using any number of repeated ‘that’s.
Let’s start by breaking down the five-that example. We start with a sentence that includes a that quotes from somewhere else: “The teacher thought the ‘that’ the student used was extraneous.” We can then begin to pile in our own extraneous thats, placing them around the quoted that: “The teacher thought that the ‘that’ that the student used was extraneous.” Closer, but not there yet. Of course, in everyday speech, people say “that that” all the time — “I don’t know what it was that that man was thinking”, “She said that that has not changed yet.” So we just reference everything with thats, and we’re good to go: “that that ‘that’ that that”.
But since we’ve come this far, we might as well go a little nuts. After all, we’re quoting a ‘that’ in there, aren’t we? What can’t that that (uh oh) refer to its own set of nested that statements?
“The teacher said that that ‘that that “that” that that’ that that student used was definitely extraneous.”
The nesting here can be, of course, infinite.
Now, winners. (You can read the answers by clicking on the notes link on the original post.) shouting-love answered it the precise way I did, with the centered quoted that. Phonic Shotgun instead quoted two ‘thats’ into his answer. thisisthebookthatiwrite, I’m not entirely positive that the comma you used was strictly grammatical, but close enough. serratedserenades used a similar construction - a dash to offset one of the thats for redundancy. And, just to drop names, harperbooks mentioned their Latin teacher using the “had version”, which I assume is James while John had had had had had had had had had had had a better effect on the teacher. Phew!
I mentioned the puzzle as coming from David Foster Wallace, and that’s definitely where I first heard it, but I have no idea if it’s older than that; it probably is.