June 9, 2011 -- "Sports Guy" Bill Simmons might just be the most successful professional sports fan of all time, getting paid to watch four hours of sports TV every day and then write about it -- or even just talk about it.
"It's a good life. I like it," he said, laughing.
A Web content-generating machine, Simmons, 41, has built up a laundry list of titles: columnist, podcast host, author, producer of ESPN's "30 For 30" documentary series, and he's now thrown his weight behind Grantland.com, the new ESPN-owned sports and pop culture website, as part of his transition away from his column.
"The new website is going to be 70 percent sports, 30 percent pop culture, and it's going to try to fill up some of the voids that I feel like are out there," he said.
Based at ESPN in Los Angeles, Grantland, which launched Wednesday, will showcase a powerhouse roster of writers, including pop culture critic Chuck Klosterman and Malcolm Gladwell, the best-selling writer for The New Yorker. Nevertheless, Simmons insists that he's still the "Sports Guy."
"I've got the title, but I'm old now," he joked. "My son slept until 7:20 today, and I was excited it was the latest I've gotten up in five years."
Touted as a pioneer of the Web, Simmons has been writing his "Sports Guy" column for ESPN.com over 10 years. He started it in Boston, where he was one of the first web-only columnists that existed anywhere.
"I was one of the first people who realized, 'Hey this is different from newspapers, this is different from magazines, how do I take advantage,?'" he said.
The concept for the column stemmed from Simmons' goal to write from perspective different from the average sports reporter.
"I had to figure out a way to write the column in a way I could pull the reader where I was when I wasn't going into locker rooms," he said. "So I wrote about things my friends and I were talking about, arguing about sports movies, talking about players, not in the way that reporters were doing it, going into the locker room, getting quotes."
With a typical column reaching the 6,000-word range, Simmons is a man with opinions on everything from Larry Bird's divinity ("I call him basketball Jesus," he said. "His autobiography, 'Drive,' we refer to as the Bible in my house."); to Lebron James' facial hair: ("The beard was awful. I forgot how weird the beard was."); to Gene Hackman's coaching ability in the iconic 1986 movie "Hoosiers" ("Bad coaching here too... Jimmy's missed one shot the whole game and you decide to use him as a decoy for the biggest player of your season -- what coach would do that? He was overrated.")
Movie references are a staple in Simmons' columns, and he admits a weakness for possibly over-utilizing his favorites.
"The ones I actually use too much are 'Boogie Nights,' any of the 'Rocky' movies, 'Shawshank' definitely, probably, and 'Godfather,'" he said. "I need to wean myself off of those four."
A hopeless Boston sports fan, he's still pained by the memory of Red Sox first baseman Bill Buckner's fielding error during Game 6 of the 1986 World Series, which may have that cost the Sox a long-sought Series title. The Buckner moment still ranks in the "top 7 or 8" worst moments of his life, he said.
Jimmy Kimmel Jokes That Bill Simmons Is 'Not a Very Good Athlete'
Simmons has garnered a wide audience, with more than 1.4 million Twitter followers and hundreds of thousands of readers every month, including late night comedy host Jimmy Kimmel.
When Kimmel was the host of Comedy Central's "The Man Show," he said Simmons' column was his homepage.
"Sports takes itself very seriously," Kimmel said. "Sometimes they have fun, but for the most part, there's a lot of self-righteousness?and Bill mixed sports and television and movies, and it's not so much a sports column as much as it is the kinds of stuff you talk about with your friends."
In fact, Kimmel liked Simmons' column so much that he hired him to write for his show, "Jimmy Kimmel Live" on ABC, when it launched in 2003.
"There are personalities that have come out of the Internet, but most of them are clowns, most of them are people playing with a light saber and singing crazy songs," Kimmel said. "Bill is someone who is actually creating quality material for the Internet, and I think he's one of the first people to do that."
Simmons left Kimmel's show in 2004 to return to his ESPN column, but the comedian, who remains Simmons' close friend, also is the keeper of some of his secrets.
"Bill's not a very good athlete," Kimmel said. "'The Sports Guy' -- not such a sports guy! 'Sports-watching guy' should be his name."
Simmons' questionable sports abilities are not the only criticism he hears. Some have said that his columns are too wordy and that his 700-page best-selling book, "The Book of Basketball," is too long.
Former MSNBC commentator Keith Olbermann took a particular dislike. He blasted the Simmons last year on his show, saying, "I am again left to marvel how somebody can rise to a fairly prominent media position with no discernible insight or talent."
While Simmons acknowledged that there are some people who don't like what he does, he said it's all about striking a "balance" with those that do.
"I think it's the law of averages," he said. "If you have anything, you have a lot of readers, and you're also going to have a lot of people who don't like reading you. It just seems like there's going to be a balance."
Forging ahead with Grantland.com and sort of leaving "The Sports Guy" behind, Simmons said that regardless of his professional progress, his ultimate legacy lies in making sure his kids don't grow up rooting for anyone but Boston, particularly the longtime Red Sox foe, the New York Yankees.
"I would just feel like I had failed as a parent [if they were Yankee fans]," he said. "I'm not going to let that happen."