Andrew Sullivan points me in the direction of "Politics and the English Language," a classic essay by George Orwell. I've listed some gems.

On Fascism:

The word Fascism has now no meaning except in so far as it signifies "something not desirable."

On modern English:

I am going to translate a passage of good English into modern English of the worst sort. Here is a well-known verse from Ecclesiastes:

"I returned and saw under the sun, that the race is not to the swift, nor the battle to the strong, neither yet bread to the wise, nor yet riches to men of understanding, nor yet favour to men of skill; but time and chance happeneth to them all."

Here it is in modern English:

"Objective considerations of contemporary phenomena compel the conclusion that success or failure in competitive activities exhibits no tendency to be commensurate with innate capacity, but that a considerable element of the unpredictable must invariably be taken into account."

This is a parody, but not a very gross one.

On political euphemisms:

Consider for instance some comfortable English professor defending Russian totalitarianism. He cannot say outright, "I believe in killing off your opponents when you can get good results by doing so." Probably, therefore, he will say something like this:

"While freely conceding that the Soviet regime exhibits certain features which the humanitarian may be inclined to deplore, we must, I think, agree that a certain curtailment of the right to political opposition is an unavoidable concomitant of transitional periods, and that the rigors which the Russian people have been called upon to undergo have been amply justified in the sphere of concrete achievement."

The inflated style itself is a kind of euphemism.

Here are David Foster Wallace's solutions to the "that that that that that" puzzle. If you want to play along, you might want to click the preceding link and read the puzzle before viewing the solutions below.

Now:

Five
"He said that that that that that writer used should really have been a which."

Six (using what DFW calls the "medial-question-mark-in-sentence trick")
"He said that? that that that that that writer used should have been a which?"

But I prefer Nacho's solution:

Eight
"Do you know that that “that” that that “that” that that Nacho bolded precedes is italicized?"

If you're having trouble parsing that, check out his explanation.

David Foster Wallace says in The Oxford American Writer's Thesaurus:

It so happens that you can occupy a bright child for most of a very quiet morning by challenging her to use that five times in a row in a single coherent sentence...

(Bold emphasis mine.) I consider a "bright child" in DFW's world to be an adult with above-average intelligence in my world, so why don't you all give it a shot? You may want to think of your answer before looking at any comments.

I'll update with the answer in a day or two.

Update: Here's the solution.