I'm having a hard time understanding the thesis of the Deadspin comparison of Dane Cook to Louis CK. I love the idea of over-analysis, naturally. But I think this is just expositional masturbation. (Which of course means I love it. But I'm worried that it's pretty meaningless).
To address one of the questions they raise: Yes. Critically acclaimed comedians ARE more similar to each other than non, that's just the cycle of criticism. If someone showed up sounding like Lou Reed today, nobody would really give a shit. But Lou Reed back then was critically huge because the idiom of rock music didn't have a "you don't need polished music, you just need honesty" standard-bearer. At that point, half-competent unpolished music was important by virtue of it's visceral nature and lack of polish, but today that doesn't do anything to move the art form forward. That happened to comedy in the mid nineties, after the sienfeld era was over, it became enough just to talk about your life, with a dash of humor.
Today's most critically acclaimed comics are the ones who are the funniest while being the least universal. Louis CK is just plain funny but when he calls his daughter an asshole or used the N-word and the F-word like he owns the place, that's pretty challenging to pre-existing standards. So Louis wins for being effective AND avant-garde. Jeff Dunham, on the other hand, has jokes that a five year old can appreciate, which means that to enjoy his jokes, critics wouldn't be utilizing any portion of their brain that makes them feel smarter than anybody else.
Dane Cook is a critical disaster, because his point of view is always over-amplified by his high energy (and, obviously, loudness). It doesn't take a genius to like a loud, overly-confident person making fun of things, which is why so many teenagers love him and critics hate him (and that goes for back in 1999, when his jokes were actually effective for their own quality--as opposed to today, as his jokes are watered down by the heaviness of his personality and the amount of material being required of him yearly by trillionaires).