Origins For eight years following grad school, Simmons lived in
Charlestown working various jobs. mainly "answering phones... organizing food runs, [and] working on the Sunday football scores section." unable to get a newspaper job, Simmons "badgered" into giving him a column, and he started the web site
BostonSportsGuy.com while working as a bartender and waiter at night. His second column was "Is
Clemens the Antichrist?", which became one of the most e-mailed articles on the site that year. In the first sixteen months Simmons wrote for Page 2, its viewership doubled. Simmons wrote a column per month for his page titled "Sports Guy's World." As a lead columnist, conceived the idea for
30 for 30, a series of 30
documentaries commemorating the 30th year of the "ESPN era." The series premiered in October 2009, with "King's Ransom" directed by
Peter Berg. Simmons served as
executive producer on the project until he left ESPN in 2015. In May 2007, Simmons began a
podcast for ESPN.com called
Eye of the Sportsguy. In June 2007, the podcast was changed to
The B.S. Report with a new theme song written by
Ronald Jenkees. Simmons created one or two hour-long podcasts a week, generally carrying one theme throughout, talking to everyone from sports and media notables to his friends. averaging 2 million downloads a month. Simmons began writing a bi-weekly but convinced ESPN after three years to give him 1,200 words. In October 2007, it was announced that Simmons joined the television series
E:60 as a special contributor. In May 2010, it was reported that Simmons and ESPN came to an agreement on a new contract, although no official announcement was made on the terms. Since 2009, Simmons has also been a moderator and panelist at the annual
MIT Sloan Sports Analytics Conference. Starting in the
2012-2013 NBA season, Simmons joined the
NBA Countdown pregame show as a panelist/contributor during ESPN/ABC's coverage of the
NBA. He left the show prior to the 2014–2015 season in order to debut
The Grantland Basketball Show, ESPN's first Grantland-branded television program. ESPN announced in May 2015 that Simmons' contract, which was due to expire in September 2015, would not be renewed.
Jimmy Kimmel Live! In the summer of 2002,
Jimmy Kimmel began trying convince Simmons to write for his new
late-night talk show, which was to premiere after
Super Bowl XXXVII the following winter. Simmons refused for most of the summer because he did not want to cut back on his columns and move to the West Coast away from his family and Boston teams. Simmons left Boston and moved to
California in November 2002 and began working in April 2003 as a comedy writer for the
Jimmy Kimmel Live!. Simmons has since referred to it as "the best move [he] ever made." after a year and a half of writing for the show, in to focus full-time on his column. The website's name was a reference to deceased sportswriter
Grantland Rice, Sports blog
Deadspin had previously reported in 2010 that Simmons was working on a "top secret editorial project." Some key contributors to the website included
Jalen Rose,
Zach Lowe,
Kirk Goldsberry and
Wesley Morris. In August 2014, ESPN announced that Simmons would be leaving
NBA Countdown to produce an 18 episode primetime show for ESPN through his site called
The Grantland Basketball Show—later changed to
The Grantland Basketball Hour—which would debut in October 2014. In these episodes, Simmons discussed NBA-related current events as well as some of his more popular sports columns with his co-host Jalen Rose. Special guests included fellow journalists, pop culture celebrities, as well as current and former coaches and athletes. Months after ESPN decided not to renew its contract with Simmons, ESPN shut down the Grantland website on October 30, 2015.
HBO In July 2015, Simmons announced he had signed a new multi-platform deal with
HBO starting in October 2015. As part of this deal, he would host a weekly talk show,
Any Given Wednesday. The show premiered on June 22, 2016. It was cancelled in November 2016. Simmons's multimedia deal with the network continued, and he announced plans for future projects at HBO. The documentary aired on
HBO on April 10, 2018. In late July 2018, it was revealed HBO decided to renew Simmons's contract to remain with the network moving forward.
The Ringer Simmons announced the launch of his new website,
The Ringer, on February 17, 2016. The site was to be run as part of his venture, the Bill Simmons Media Group, that launched in the fall of 2015. The media group includes several podcasts focusing on different aspects of sports, pop culture, and technology, and features writers from The Ringer website as podcast hosts. The website also hired a number of staffers who formerly worked with Simmons at Grantland. In May 2017,
Vox Media announced it had entered into a deal to provide advertising sales and access to its publishing platform as part of a revenue sharing agreement. Simmons retained editorial control of the website. In February 2020, Simmons announced that
Spotify was buying The Ringer for approximately $200 million, with
Daniel Ek describing The Ringer as "the new ESPN." Simmons stated that The Ringer would maintain content and editorial independence. At The Ringer, Simmons is CEO, writing less than during his previous endeavors. He also hosts
The Bill Simmons Podcast, which regularly rotates through conversations and interviews with Hollywood personalities, professional athletes, other media
pundits, old friends, and his family. Regulars include his college roommate Joe House,
Sal Iacono,
Ryen Russillo,
Chuck Klosterman, and Simmons' father. In June 2020, Simmons received criticism for the lack of racial diversity in The Ringer following email comments he made to
The New York Times, particularly that: "It's a business. This isn't Open Mic Night." Critics noted that Simmons employed his nephew as a producer and had created a podcast for his teenage daughter. In October 2025, a number of Ringer podcasts, including
The Bill Simmons Show, were acquired by
Netflix for exclusive video distribution on the Netflix platform. ==Writing==