#115: Part 1 With Imperial Twilight: Did Bill Help Destroy Sportswriting? Plus, Bill's Evolution From Fan to Rich LA Insider, Why Hasn't He Been Cancelled & Challenging Russillo's Tape Grinding Claims

The r/BillSimmons Podcast

Welcome to Episode #115! We had on fellow podcaster Imperial Twilight and went for over two hours - so like our recent two episodes, we're breaking this into two parts.

We kick off Part 1 by talking about Bill's background - how much of his persona is real and how much has he exaggerated his Boston fanhood over the years? Imperial thinks Bill's everyman sports fan persona is more of a LARP than what's been let on.

Next we ask whether Bill is more of a homer now than he used to be - or, is he simply a more insufferable homer now? Is Bill worse when his teams are good or bad? We discuss his strong dislike of Pete Carroll in the late-90s when Pete was actually a decent coach, and how Bill became the poster boy in the 2000s for the annoying Patriots fan. We discuss how the perception of Simmons' homerism has changed since he stopped writing.

We then talk some Simmons & Russillo and challenge Ryen's tape grinding - have they discussed the new NBA trends in inbounds passes? It appears not - so how much tape is Russillo really grinding? And we wonder about Cousin Sal's humor - why is he not funny at all outside of the Simmons pod? And how was Kimmel funny on his late night show when Bill and Sal were writing bits? We also reminisce about some of Carolla's epic movie pitches including Pedof-Isle

Did Bill Simmons change sports writing or did he destroy it? Imperial argues that Bill's initial foray into the medium changed sports writing and eventually destroyed it. Bill created a lot of copycats and diminished the idea that the beat writers had unique insights - and why not read a fellow fan? Imperial tells us a story of talking 3 hours with Bob Ryan and his meticulous preparation and work that went into writing about the Red Sox; could Simmons could have ever been a Bob Ryan; working sources, being on-site, talking with front offices.

Next we hit on Bill's evolution over the years. Did Simmons evolve from everyday sports guy to rich guy? Was Simmons always the rich guy at heart? How and when did he go from outsider to insider? We talk about the evolution where Bill went from "I'm a sports fan like you" to "I'm Bill Simmons"; Imperial remembers when Bill covered Super Bowl week without even staying for the game. We next hit on 30 for 30 and how some of the details they left out in certain docs showed that Bill was becoming an insider quickly, and that this went against one of Bill's original premises of his writing - calling out the insiders.

We finish up Part 1 asking why Bill sat out the 2024 Podcast Election - how did the Podfather not partake? And why didn't Bill claim he felt vindicated as a podcaster when they factored so heavily into the election outcome? We ask why Kamala didn't go on his pod, and wonder why hasn’t Bill been the subject of cancellation attempts with all the content from his past.

If you liked the show, be sure to stay tuned for Part 2. Follow Imperial on Twitter at @ImperialTwilite and listen to his podcast on his substack at https://imperialtwilight.substack.com/