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This is just a theory.
I read a story about how he was one of the first stand up comics to use the internet to promote themselves on a massive scale. This was back in the Myspace days and he would send out mass emails and promote himself. At one point he had one of the most popular pages on the site.
My theory is that this allowed him to bring stand up comedy to many people who would otherwise not really follow it and they liked it because, well, they didn't know any better. Not to mention, if you expose yourself to millions of people you will no doubt find some of them that like your brand of humor. It is all a numbers game and Cook figured out how to play it.
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