92: Synecdoche, New York with Angie Han

Phil and Emily are joined by Angie Han, TV critic at The Hollywood Reporter, to discuss Synecdoche, NY (2008), Charlie Kaufman's audacious directorial debut and the film Roger Ebert called the best of the 2000s. Kaufman wrote and directed this hallucinatory portrait of Caden Cotard (Philip Seymour Hoffman), an ailing theater director who uses a MacArthur Fellowship to build a life-size replica of New York City inside a warehouse. As the decades pass and his art consumes his life, the film tunnels deeper into mortality, creative obsession, and the quiet horror of living in a body that won't cooperate. Originally conceived as a horror film with Spike Jonze, Synecdoche, NY opened in October 2008 against High School Musical 3 and Saw 5, made $4.5 million on a $20 million budget, and has since been ranked among the greatest films of the 21st century by the BBC, the Guardian, and Time. Phil finds it deeply triggering as a self-described hypochondriac. Angie has seen it a dozen times and finds it weirdly soothing. Emily thinks it's funnier than people give it credit for. All three dig into why this film bombed commercially and became a critical touchstone, what it means to watch it in your 20s versus your 40s, and why it still doesn't have a Criterion edition. Follow the show and guests: Podcast Like It's... — Phil Iscove — Emily St. James — Angie Han — 💜 Patreon (bonus episodes and video): Hosted on Acast. See acast.com/privacy for more information.

You can listen to 92: Synecdoche, New York with Angie Han online on Radio and Podcast. Open the player on this page to stream the available audio.

92: Synecdoche, New York with Angie Han is an episode from Podcast Like It's 1999 by Phillip Iscove.

This episode is 1:37:24 long.

This episode was published on May 1, 2026.

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