Bill Simmons Is De-Apexing

It's been an eventful year for Ringer founder and podcast host Bill Simmons. He ended 2025 and began 2026 at a peak in popularity, thanks to his performance on a podcast titled "Bill’s 50 Most Rewatchable Movies of the 21st Century," which earned him the kind of crossover appeal he's rarely enjoyed. Just before that, he signed a deal to have to have several Ringer podcasts licensed to Netflix. Then he got to tell the world about how the Jaylen Brown trade happened during his colonoscopy. For the last eight months or so, Simmons has been, to borrow a phrase, on Apex Mountain. But mountains are slippery, and Simmons has been steadily sliding back to sea level over the last few months. Consider the following pieces of information: During episodes of The Rewatchables, Simmons established a new segment in which he uses ChatGPT to produce, in Roger Ebert's voice, a review of a movie that Ebert never got to write about, on account of him being dead. ChatGPT recently became a presenting sponsor of The Bill Simmons Podcast, and during his first attempt at reading the ad copy he pronounced it "ChatGBT." On the Aug. 9 episode of his podcast, he once again brought up the fact that he does not wear a seatbelt when he drives. On the Aug. 25 episode of a Ringer podcast about historic box-office flops, he wore an Anduril hat. Where one even acquires an Anduril hat is not a question that can be answered by a person in my tax bracket. On the most recent episode of his podcast, he gave a detailed description of his participation in proxy betting. Because he lives in California, where sports gambling has not been legalized, he calls his daughter's boyfriend, who lives in a state where sports gambling is legal, gives him his FanDuel login information, and has the boyfriend place bets on his behalf. FanDuel, with whom The Ringer signed a lucrative sponsorship deal, explicitly prohibits proxy betting.

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