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.

In addition to all this, there appears to be some dissent within the ranks. Sean Fennessey and Amanda Dobbins, co-hosts of The Ringer's movies podcast, were recent guests on a podcast called Talk Easy. Two specific moments were clipped and widely aggregated (Gah! The aggregators!), in which Dobbins and Fennessey seemed to be at odds with their boss's decision-making. In the first, Fennessey says he doesn't like it when Simmons does the Roger Ebert ChatGPT bit, and Dobbins is shocked to discover that ChatGPT sponsors podcasts on The Ringer:

In the second, Fennessey expresses some consternation over the fact that his podcast has been licensed to Netflix, as the deal creates a conflict any time he wants to cover a movie that is released by Netflix.

A couple things: Media industry job titles have never been more fake. How else do you explain a guy whose name is near the tippy-top of The Ringer's masthead saying, "It's not my decision," when asked why he doesn't prevent a chatbot from puppeteering Roger Ebert's corpse on a podcast he co-hosts? Also, while I take Fennessey's point about the conflict being raised by his company's licensing deal with Netflix, wasn't The Ringer producing a weekly TV show about Game of Thrones that aired on HBO way back in 2016? That horse left the barn a long time ago, brother.

As for Simmons, he'll surely come out of this run of mildly bad press unscathed. If he wants to hurry up the process and put the spotlight on someone else's questionable moral and business decisions, he can always just remind everyone that Andy Greenwald, the co-host of one of his company's longest-running podcasts, is a consulting producer on the new Harry Potter show.