90: Confessions of a Dangerous Mind with Jason Bailey

Phil and Emily are joined by film critic and author Jason Bailey to revisit Confessions of a Dangerous Mind, George Clooney's 2002 directorial debut based on Chuck Barris' unauthorized autobiography. Jason is the author of Gandolfini: The Real Life of the Man Who Made Tony Soprano, now available in paperback. Chuck Barris created The Dating Game and The Gong Show. He also claimed to have secretly killed 33 people for the CIA. Charlie Kaufman wrote the screenplay, Sam Rockwell stars as Barris, and Drew Barrymore and Julia Roberts co-star. Before Clooney made it, the film passed through David Fincher, Darren Aronofsky, Sam Mendes, Bryan Singer, Johnny Depp, Ben Stiller, Sean Penn, and Mike Myers over nearly a decade of development. The three dig into what Clooney kept and what he stripped from Kaufman's original script, whether Sam Rockwell's performance holds the whole thing together, and what Roberts and Barrymore bring to a film that never quite commits to its own tonal chaos. They also get into Clooney's arc as a director, a genuinely promising debut followed by a filmography of diminishing returns, and whether Confessions of a Dangerous Mind holds up as his most interesting work two decades on. Jason says yes, unequivocally. Emily loved it then and is reconsidering. Phil never fully clicked with it. They all agree the ending is something close to perfect.+ Follow the show and guests: Podcast Like It's... Phil Iscove: Emily St. James: Jason Bailey: Patreon (bonus episodes and video): Hosted on Acast. See acast.com/privacy for more information.

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90: Confessions of a Dangerous Mind with Jason Bailey is an episode from Podcast Like It's 1999 by Phillip Iscove.

This episode is 1:35:54 long.

This episode was published on Apr 17, 2026.

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