Not quite righteous enough for the win, but still bringing the heavy PWNage for a Runner-Up position:
http://sandiego.craigslist.org/csd/app/1429984086.html" rel="nofollow">Air conditioner - evaporative type - $33 (Normal Heights)
Does it get the nod for the nonchalant "yeah, we suppose this is the wrong time of year to be selling this" tone? Nope. For the ambivalent pricing strategy? Nope. It gets the Runner-Up spot because of http://en.wikipedia.org/wiki/Evaporative_cooling#Evaporative_cooling" rel="nofollow">this. Intrigued by "evaporative cooling," I did some research. Fascinating stuff! Especially the parts about evaporatively cooled airplane engines during the Thirties and the fact that evaporative coolers make use of something called http://en.wikipedia.org/wiki/Excelsior_%28wood_wool%29" rel="nofollow">excelsior.
When all is said and done, tricking me into learning something isn't quite enough to clinch the big victory. What is it that takes it to the next level, goes above and beyond? Well:
http://sandiego.craigslist.org/csd/for/1430620266.html" rel="nofollow">30 Gallon Hot Water Heater (GAS) - $50 (Normal Heights)
Nothing screams "going above and beyond" quite like redundancy!
Hmmm, whatever shall I do with all this hot water I have lying around? Ah ha! I shall heat my hot water! But how? Of course, with a Hot Water Heater--the last heater for heating hot things you'll ever need! Plus, at the bargain basement price of $50, I just have to swing by the ATM machine and grab a little cash. I consider myself lucky, living in a world where I'm never too far from an Automatic Teller Machine Machine.
Redundancy occurs in speech too. The phrase "equally as" pops up in conversation all the time, e.g. "equally as unnecessarily redundant." Very strange. Not by any means as strange as the warped construction "a whole nother." As opposed to the first nother? Or maybe some other nother? The "nother" pops up in http://en.wikipedia.org/wiki/A_Whole_Nother_Thang" rel="nofollow">all sorts of places within the twisted lexicon of modern English.
"Aw, c'mon, Pike" you want to say. "That's just the evolution of the language. Give it a break."
Which, of course, raises an interesting point. Somewhere back amongst the foggy ruins of time there was a point at which the language was much more flexible. Heck, read "Gawain and the Green Night" and the same word receives different spellings within the confines of the same verse. And that's Middle English. Old English is basically unreadable. Even much later, things were still in flex. Everyone has some comment on the enormity of Shakespeare's contribution to the language. Words from "alligator" to "puke" are attributed to his invention.
Broadly speaking, it's seems to me as though the evolution of the language has gradually slowed over the past millennium or so, with a possible terminus at the acceptance of the Oxford English Dictionary as the definitive record of what words are and are not part of the grapholect. Then again, bizarre neologisms ("PWN" or "w00t" being personal favorites) want nothing more than to show us that there's plenty of room in the books for new words.
Of course, that doesn't necessarily indicate that things are still evolving. Variations within a theme don't strictly count as outright changes. Look at the biological evolution of homo sapiens: literally hundreds of thousand of years of growth and devlopment separate twenty-first-century peoples from the earliest iterations of human-kind. We've gone from cave painting to Rothko, from pointy sticks to iPhones. Yet we remain the same species, simply varying within the theme.
Now, I'm neither an evolutionary theorist (I mean, I'm fond of the http://en.wikipedia.org/wiki/Aquatic_ape_hypothesis" rel="nofollow">aquatic evolution theory, for it's novelty if nothing else) nor do I really see the point in questioning the finer points of these things. I'm deliberately painting this picture of human/linguistic evolution in very broad strokes to illustrate an interesting tangent, borrowing tools and terminology, adapting them to my purposes. If anything, I think the idea that the evolution of a language might be closing down--if not already closed--fascinating. At what point does change become impossible from within a given paradigm? Is it feasible that language (or even biology) might be headed towards a sort of degree-zero? Can that degree-zero actually be achieved, or is the movement inherently asymptotic, with every new "PWN" or "w00t" representing another incremental step towards nonsense and a self-sustaining attempt to keep things moving when there's nowhere to move to?
Either way, I doubt the hot water really needs heating...