I'm not sure Josh's logic quite works as to what is correct versus what sounds stupid.
However, the National Association of Good Grammar (NAGG... really) published a statement that "Twenty Ten" was what they decreed we should use.
Admittedly, they didn't say it was correct because, mathematically, "Two Thousand Ten" is the proper verbal date. "Twenty Ten" was recommended not because it's correct (as it's not) but because English speaking societies tend to shorten dates in this manner (as evidenced from "Nineteen Ninety Nine") for brevity. In spite of of all those many years of speaking it incorrectly - culturally it's the norm. Hence the recommendation of "Twenty Ten." Again, culturally, Twenty follows Nineteen so the weight is given to how we've grown accustomed to saying things. It's been wrong all these years but we've at least been consistent.
The hope was to stave off this horrible, kitten-killing, cultural habit of calling it "Two Thousand..." as so much ground was lost in the single-digit years (2000-2009) that it was felt now was the time to take a stand once and for all lest we truly screw ourselves into the ground by not getting out of the habit.
There was a certain irony in reading the author's statement in that he referred to these previous years as "aught" and then the number ("Twenty Aught Nine" - the year we just completed). This didn't phase him.
He did, however, acknowledge this only goes so far in things concerning cultural habits... such as Arthur C. Clarke's books "2010: The Year We Make Contact" or "2001 A Space Odyssey."
Linguistics Professor George Lakoff said:
""It's not wrong to say 'two thousand ten... and it's not like 'twenty ten' is the right way."
His explanation involves cognitive reference points, standards of speech and recognizing as anachronistic the notion that grammar can be right or wrong as people and cultures evolve."
He agreed that Twenty Ten would take over because it's how we roll.