Why is Bill Simmons the funniest writer on the internet? This is a topic I've been pondering for some time. I don't have all of the answers, but I do have a lot of them.
1) Since he's not close to the people he writes about, he is willing to write negatively about them. So, if he does give a player praise I pay attention because it is unlikely to be simply politically correct hackery. Unless it is about the Red Sox. He also pushes boundaries regarding the WNBA all the time, so much so that I almost feel guilty reading it. But ultimately his willingness to push envelopes is a good thing and it separates him from the pansies who are worried about some vague and distant future.
2) Many of his ideas are outrageously overambitious. He once claimed to be doing a series on the "Best 72 Sports Movies of the Past 33 Years," wrote up 8 of them in a haphazard order, and hasn't written a thing about them in 4 years. This ambition infects all of his ideas, including the "Real Men of Genius Hall of Fame," countless variations of fantasy sports, and that a few kids should tape their attempt to reenact Ferris Bueller's "eight hour" escapade in Chicago to see whether it is possible. Most of these ideas will never come to fruition, but that doesn't matter to me.
3) He loves lists. I love lists, too.
4) His knowledge of intentionally or unintentional comeies of the 1980's and 1990's is nigh-encyclopedic, and he references specific moments in them all the time. Theoretically, every time he does this he risks alientating readers that don't understand the reference. But in practice this doesn't seem to be an issue. Perhaps the people that do understand the reference feel that they can relate especially well to him and become more loyal, and this benefit more than outweighs the costs. Or perhaps I am simply underestimating how many people have seen these movies. At the end of the day, Shawshank is the number one movie in the world, ever, The Godfather is number two, and the rest of the movies he refers to aren't so shabby either. Because if you have seen the movies the references are sometimes hilarious. Indeed, I went out of my way to watch both Teen Wolf and Boogie Nights in large part so that I could understand what Simmons was writing about.
5) The e-mails that he posts from his readers are legitimately funny. This fact is usually attributed to the quality of his readers, but to me the simpler explanation is that his own comedic filter is highly refined. To be funny in real life, one must be quick witted. But to be funny on the internet, the most important quality is to be able to recognize whether or not something is funny, because time is not really the primary constraint. Thus, it is one's sense of humor that truly separates the heavyweights from the welterweights on this strange and newfangled series of tubes.