If you harbor any aspirations of being a writer, and are looking for some inspiration, the story of Bill Simmons isn't a bad place to start. Back in the late '90s, the Massachusetts native was writing by day and bartending by night (albeit with a master's in journalism from Boston University and three years with the Boston Herald under his belt), debating just what to do with his life, when he decided to dedicate himself to writing about the thing he held most dear: Boston sports. Dubbing himself the "Boston Sports Guy," he started a blog, which was promptly picked up by AOL's Boston site, and readers flocked to it.
Gone was the inherently faulty assumption of impartiality; finally, a sportswriter was tackling sports in a way readers could connect to on a level that was practically primal! Not only that, but Simmons' writing style was perfectly suited for the new digital platform; the disappearance of word counts limited by the tyranny of column inches meant he could embrace his enthusiastically verbose style. (This is, after all, a man who just last week confessed on his podcast that he "can't even fart in 680 words.") And his lack of desire to draw a line between his love of sport and his fondness for all other facets of pop culture (weaving TV and film analogies throughout his columns, along with as many 90210 references as humanly possible) only served to open the door to an even larger readership.
Simmons landed at Page 2, the less traditional, more irreverent section of ESPN's website. While maintaining his ever-popular column, he also managed to pull off a year-and-a-half long stint as a writer for Jimmy Kimmel Live!, and write two bestsellers: Now I Can Die in Peace, his treatise on his tumultuous life as a Boston Red Sox fan; and The Book of Basketball, a 754-page tome on all things hoops. On top of all that, this phase of his career also saw the launch of his hit podcast "The B.S. Report" in 2007, and the establishment of the company's much-celebrated documentary series 30 for 30 in 2009, which Simmons had a big hand in shaping.
This led to Simmons carving out his very own slice of ESPN's Internet presence: the much-beloved, and recently dissolved, Grantland. With Grantland—named in honor of legendary early 20th-century sportswriter Grantland Rice—Simmons was able to build an outlet through which his love of pop culture would no longer need to be relegated to footnotes; it shared top billing with the sports coverage.
Grantland embraced longform writing, and ushered a number of up-and-coming writers into the spotlight, running pieces on everything from Sumo Wrestling to Broad City to the crisis in Ferguson, MO. Sadly, the site met its end shortly after a public fracas between Simmons and the parent company; he rode out the remaining days of his expiring contract in a vow of media silence.
Then came the news that Simmons had struck a deal with HBO for a weekly talk show, and the return of his podcast. His fans welcomed this with open arms, but were left waiting to learn what was to be the fate of his column-writing. They began to breathe easy once more with the announcement last month of his new website, The Ringer. For now, theringer.com houses only a logo and a cryptic description—but on a recent episode of his podcast, Simmons has indicated that a newsletter should be launching in the coming days.
Bill Simmons made his name with an approach to sports writing that paired two deeply relatable aspects of fandom—reckless emotional abandon, and deep-dive obsessiveness—and he showcased an eye for talent with his stewardship of Grantland. The unveiling of the Ringer leaves his fans optimistic that those practices are all alive and well.
Ready to become Bill Simmons's biggest fan? Familiarize yourself with these five stand-out pieces before The Ringer launches.
In his introductory Grantland column, Simmons shares his experience of working for Jimmy Kimmel Live! in its formative days, writing with the unique brand of excitement that accompanies the start of a new project.
When a move to L.A. means he can't uphold his annual tradition of watching the NBA Draft with his dad, Simmons uses his column to muse about the beautiful lunacy of his father's love of New England sports, and how it informed his own path.
To stay on top of all Simmons-related affairs, feel free to obsessively check up on theringer.com until it goes live.