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."