Bill Simmons is my favorite columnist and his columns provide critical analysis and deep humor. He writes for ESPN.com and ESPN the Magazine and you can find his writings at the Sport's Guy's World. Prior to being hired by ESPN, he ran his own site called The Boston Sports Guy. Part of what makes him so great is that his success highlights the meritocracy of the internet. He was a guy blogging about sports who was so funny that he was hired by the preeminent sports brand and is now one of its biggest draws.
Bill's writings sit at the intersection of sports and pop culture. He also details many aspects of his personal life. While his writings get publicity for their humor, his analysis is extremely thorough and he calls attention to often overlooked themes. For example, in writing about the 2009 NBA Finals he explored the following theme: Did the '09 Lakers really like each other, or was it like a Bill-Hillary thing?
My favorite columns are the draft diaries (he keeps a running journal as he and his father watch the NBA draft commenting on the players' clothes, entourages, awkward hugs with David Stern and the ridiculous commentating by the announcers who use phrases like tremendous upside potential), his travel recaps (where he details his weekend in Vegas with friends or trips to the Super Bowl or All Star Games, and mailbags (where readers submit questions and hypotheticals and he answers them eg. Q: Did your Clippers just win the draft lottery or did Blake Griffin lose it?
His pop culture references are hilarious as he weaves asides about The Karate Kid, the Real World/Road Rules Challenge or The Hills into thoughtful analysis of sports topics. He has also introduced certain themes which have entered into the sports consciousness like The Ewing Theory (when a team improves by losing its best player who had never won a championship) The Levels of Losing (quantifying how painful a loss is) and The Tyson Zone (where an athlete's behavior is so crazy that people would believe any story about him) In addition he has been threatened by Isiah Thomas who objected to Bill's skewering of his general manager abilities. For those of you who like sports and like laughing…check him out.
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