This might not be anything special for comics. But it works for him because he has a great every man quality, and because he's white and not Jewish, which makes him somewhat of an abnormality in comedy. As said before, he tends to cloak his observations in unbelievable storylines, but his whole shtick boils down to an exercise in making the absurd totally believable and relatable. Which he does quite well.
That said, when I was watching last night, I grew to hate Dane Cook, even though I was frequently laughing. And this is because he is a guy who knows full well that he is the most popular comedian in America.. And he knows that, looking out from the stage into the darkness, there are thousands of guys that want to hang out with him and thousands of girls that want to have sex with him. Because he knows these things, and because he's an egomaniac, he often gets lazy with his jokes, and just relies on his trademark tactic, which, when employed, makes him suck balls:
