[8] Simmons was an only child and grew up in Marlborough and Brookline, Massachusetts, before moving to Stamford, Connecticut, to live with his mother after his parents divorced when he was 9.

[12] As a child Simmons read David Halberstam's book The Breaks of the Game, which he credited as the single most formative development in his sportswriting career.

[14] He also restarted the school's parody newspaper and started a 12-14-page, underground, handwritten magazine about the people in his freshman hall called "The Velvet Edge.

in political science (his primary focus was the Middle East, which he often cites in his columns by way of saying his sportswriting career has nothing to do with his degree) and a GPA of 3.04.

[15] Subsequently, while living in Brookline, Massachusetts, he studied at Boston University, where he received his master's degree in print journalism two years later.

[1] In 1997,[18] unable to get a newspaper job, Simmons "badgered"[1] Digital City Boston of AOL[19] into giving him a column, and he started the web site BostonSportsGuy.com while working as a bartender and waiter at night.

[15] Simmons gained fame as "The Boston Sports Guy"[22] which earned him a job offer from ESPN[14] in 2001 to write three guest columns.

[35] Simmons created one or two hourlong podcasts a week, generally carrying one theme throughout, talking to everyone from sports and media notables to his friends.

[9][24][29] 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.

[9] Simmons served as the editor-in-chief of Grantland, a website owned by ESPN covering sports and pop culture that launched on June 8, 2011.

[55] A documentary on André the Giant was co-produced by HBO Sports, the WWE and the Bill Simmons Media Group, with Jason Hehir directing.

In late July 2018 it was revealed that HBO decided to renew Simmons's contract to remain with the network moving forward.

[60] On May 30, 2017, Vox Media announced that it had entered into a deal to provide advertising sales and access to its publishing platform as part of a revenue sharing agreement.

He hosts The Bill Simmons Podcast which regularly rotates through conversations and interviews with Hollywood personalities, professional athletes, other media pundits, old friends, and family.

Regulars include his college roommate Joe House, Sal Iacono, Ryen Russillo, Chuck Klosterman, David Chang, 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.

[69] The book is a collection of his columns, with minor changes and lengthy footnotes, leading up to the 2004 World Series victory by the Boston Red Sox.

[26][73][74] When Simmons first started his website, he wrote what he thought friends would enjoy reading because he never understood how people could be sportswriters while claiming they did not care which team won, in the name of journalistic objectivity.

[77][82][83] This led to Thomas threatening Simmons on Stephen A. Smith's radio show in early 2006, saying that there would be "trouble" if they ever met in the street.

[87] Simmons faced widespread critique in 2013 when he linked local fans' ambivalence about Memphis Grizzlies's chances to lingering trauma surrounding the assassination of Martin Luther King Jr.[88][89] In September 2017, Simmons voiced his support for Jemele Hill, who became involved in controversy after tweeting her personal views on Donald Trump.

[91] On April 26, 2022, Simmons drew criticism from current and former NBA players over his comment stating "...fuck Jalen Green" when discussing his choices for All-Rookie first team.

[92] Simmons later clarified that the expletive was a joke and not a personal attack, and that he was simply indicating his preference for Herb Jones as a candidate for the All-Rookie team.

[93] In June 2023, when referring to the mutual decision of Spotify and Prince Harry and Meghan, The Duchess of Sussex's Archewell productions to end a $20 million agreement and part ways after only 12 episodes of a single podcast (Meghan's Archetypes podcast) and one holiday special, Simmons labelled the Prince and Duchess "fucking grifters".

"[103] In late 2009, Simmons was punished by ESPN for writing tweets critical of Boston sports radio station WEEI's The Big Show.

[105] On September 24, 2014, ESPN suspended Simmons for three weeks for criticizing NFL commissioner Roger Goodell's handling of the Ray Rice domestic violence case.

[106][107] During his podcast, Simmons stated that Goodell was lying when he claimed that he did not know what was on the tape that showed Rice punching his fiancé in the face and knocking her out in a hotel elevator.

[106][107][108][109] On May 8, 2015, ESPN president John Skipper announced[110] that the sports media conglomerate would not be renewing Simmons's contract, which was set to expire in September 2015.

[8][112] His father, William Simmons Jr. (born 1947), also referred to as "The Sports Dad", was the superintendent of schools in Easton, Massachusetts, for more than 15 years.

[24][115] He was a longtime fan of the Boston Bruins and the NHL, but claims that their poor management led to his completely losing interest in them until the 2008 playoffs.

[121] Simmons also has created numerous internet memes, most notably the Ewing Theory[122][123] (though the idea was originally proposed by a reader[122]), The Tyson Zone[124] and the Manning Face.