Founder of The Ringer Takes Flak From Co-Hosts for A.I. Antics

By the Editorial Team · Thursday, September 3, 2026

Bill Simmons has faced backlash from co-hosts and listeners for using AI-generated content to mimic late critic Roger Ebert’s movie reviews on his podcast “The Rewatchables,” sparking ethical concerns and internal disagreements. This controversy coincides with an ongoing legal investigation into Simmons’s involvement in prohibited sports betting activities, underscoring increasing challenges around AI use and regulatory compliance in media.

Bill Simmons, the founder of The Ringer and a prominent podcaster and sports columnist, is facing criticism from his co-hosts and some listeners over his use of artificial intelligence on his film podcast, “The Rewatchables.” Simmons has employed ChatGPT, an AI language model developed by OpenAI, to simulate the movie reviews of the late film critic Roger Ebert, a practice that has drawn ire for being seen as disrespectful to Ebert’s legacy and incongruous coming from a writer.

The controversy intensified after co-hosts Sean Fennessy and Amanda Dobbins publicly expressed discomfort with the use of AI to channel Ebert’s voice, particularly since OpenAI has become a sponsor for the show. During an interview on the podcast “Talk Easy,” Fennessy acknowledged reservations about using AI-generated content in this way, stating that some members of The Ringer’s team, including himself and frequent co-host Chris Ryan, consider the practice “not cool.” Dobbins appeared surprised upon learning of the sponsorship, highlighting the tension surrounding the issue. Simmons, Fennessy, and Dobbins did not respond to requests for further comment.

The use of AI to recreate Ebert’s critiques has been a recurring point of contention among Simmons’s co-hosts and some listeners. Previous episodes featured banter over the legitimacy and appropriateness of relying on ChatGPT to replicate Ebert’s opinions, with co-hosts pushing back against the segments. Simmons has reportedly curtailed the practice at times, following co-host feedback.

The debate over the use of AI reflects broader societal concerns, including questions about copyright, creative authorship, and the ethical implications of artificial intelligence. OpenAI’s technology has been at the center of a legal dispute with a major news organization alleging copyright infringement by AI systems, a claim denied by OpenAI and its partner Microsoft.

Separately, Fennessy voiced concerns about a separate conflict involving The Ringer’s licensing arrangement with Netflix, which recently took exclusive rights to some of the company’s shows. Fennessy suggested that a film podcast covering Netflix releases might face an inherent conflict of interest under these conditions. A Spotify spokesperson, representing The Ringer’s parent company, noted that The Ringer retains creative control over its programming.

In addition to the AI controversy, Simmons addressed a recent legal issue involving his participation in sports betting. Over the weekend, Simmons disclosed that he had asked his daughter’s boyfriend to place wagers on his behalf on FanDuel, which is prohibited under Massachusetts law. The state gaming commission has since indicated it is investigating the matter. On his podcast, Simmons apologized for the oversight, acknowledging his misunderstanding of the regulations and joking about the personal consequences for his daughter’s relationship.

These incidents mark a challenging period for Simmons and The Ringer, highlighting the evolving complexities media figures face amid advancing technology and regulatory scrutiny.

This article was reported by synthesizing coverage from multiple independent news outlets to present a balanced, unbiased account. Read about our editorial standards. Spotted an error? Let us know.