WASHINGTON -- Bill Simmons is about to get on a riff.
The ESPN.com writer makes hay of commenting on the whole spectrum of sports and pop culture, but he can't really critique ESPN, a frustration he alludes to frequently in his "Sports Guy" column, read by some 500,000 people a month.
His buddy Joe House, an occasional character in the column and his tablemate at a Starbucks in Washington, smiles knowingly as Simmons works into a metaphor.
"I guess we're like T.O. and Donovan McNabb," he says of himself and ESPN. "God, I guess that makes me T.O."
He pauses to think for a moment. "I'll be T.O.," he decides.
Outside, fans in Boston Red Sox jerseys are lining up to get signed copies of Simmons' new book.
But inside, he's on to the next metaphor. He compares himself with a pitcher, signed by the New York Yankees to win 20 games but told to do so without his slider. "Yeah, I can win 20 games without the slider," he says. "But it's like if I could throw the slider, I could have a Bob Gibson season."
"We'd all like to see you with the slider," House says.
It's a combination of ego, banter with friends, wordplay and love for sports that will be familiar to Simmons followers.
But just eight years ago, the would-be Gibson of writers wasn't sure he'd ever be able to share his world with anyone beyond friends and family.
For a while, his plan to become Boston's next great sports columnist had gone fine. He had earned a campus following at Holy Cross and taken a job covering high school games for the Boston Herald. And he knew he had that voice, the one that would make readers feel they were arguing sports with a buddy on the next barstool.
But after three years, he was still organizing Chinese-food lunches and writing blurbs for the back of the section while the senior writers - ones he considered awfully pedestrian - showed no signs of leaving the jobs he wanted.
So he quit. Moped around his apartment for a while. Took a job tending bar. Until the damnedest thing happened.
Simmons started producing a Web page for America Online's digital community in Boston. He figured hardly anybody was reading, so he tried all the devices he'd always imagined - writing sports like he talked it with his pals, cracking jokes about pop culture, making his dad and his girlfriend characters.
Within a year, his friends were getting e-mails from third parties saying they just had to read this Simmons guy. Within four years, ESPN called offering an online writing job. Within five, he was balancing his ESPN columns with writing for ABC's Jimmy Kimmel Live. Last month, ESPN published his first book, a chronicle of his Red Sox fandom called Now I Can Die in Peace.
Simmons, 36, is the most successful in a new breed of online sports columnists who've made their bones without ever toiling in the local paper.
He's sort of like the king of bloggers, paid by ESPN to preside over a world he has created, one in which The Karate Kid is a classic film, referenda on his next intern can last for months and Ewing isn't the name of a 7-foot center but of a unified theory on the overrated superstar as albatross.
Simmons makes no pretense of being an insider, the traditional province of sportswriters. Instead, he taps into the collective, those conversations you have while drinking beer with your buddies - fleeting perhaps, but the essence of day-to-day friendship.
He can knock out a thousand words, easy, on an analysis of how many points Jimmy Chitwood scored in the championship game of Hoosiers. Or he can tug the emotions with a piece about the Red Sox or the late Len Bias. He's wildly parochial, writing more about the Patriots, Red Sox and Celtics than all other teams combined.
"I think part of the reason he's been so successful is that he's this new kind of sportswriter who makes the reader feel there isn't this chasm between their lives and his life," says Chuck Klosterman, a writer for Spin and Esquire who, like Simmons, is a cultural collagist. "They feel like they know this dude from somewhere else."
The late columnist Ralph Wiley once wrote to Simmons: "They want you to write about them; your stories of your Vegas rides with your boys, their P.O.V., it's so relatable to them, it's like they finally have their perspective put forth in such a funny, knowing way - a lot of them would rather be you than Roger Clemens."
Wiley nailed Simmons' intentions. He grew up feeling his favorite writers were like friends, and he wanted to create the same feeling for his readers.
Simmons says his incessant blending of sports and pop culture reflects the way he and his buddies talk.
"I mean, there are 10 phrases in Boogie Nights that if we use them, he's going to know what I'm saying and I'm going to know what he's saying," he says, nodding to his friend House.
House gives an affirming nod on the Boogie Nights bond.
"But I think it's painful when other writers try to force it," Simmons says, wondering if he has trademarked the style.