Kaufman, 66, reinvigorated Hollywood at the turn of the millennium with a series of surreal, hilarious and deeply philosophical screenplays for films like Being John Malkovich, Adaptation and Eternal Sunshine of the Spotless Mind (for which he won a best original screenplay Oscar).
As he explains on the episode, Spike Jonze, who directed Malkovich, was meant to direct the project, which was inspired by a prompt from then-Sony Pictures co-chair Amy Pascal, who asked the duo if they would consider making a horror film.
"I didn't want to do genre horror movie. I wanted to do something that was scary to me," Kaufman explains. "Illness was a big thing [that scares me], relationship struggles and alienation from others and from children, isolation and loneliness. Obviously, mortality."
What he came up with is a strange and elaborate story about a theater director named Caden Cotard (played by the late Philip Seymour Hoffman) who suffers from all the aforementioned tribulations. But after he stumbles into a windfall in the form of a MacArthur Fellowship genius grant, he decides to recreate his downtrodden life inside a massive Manhattan warehouse. The project spans decades and grows increasingly Byzantine and bizarre.
Jonze ultimately got pulled away by his Where the Wild Things adaptation, and helming duties fell to Kaufman for what would be his directorial debut.
The film featured dozens of speaking parts, filled by some of the top working actors in independent cinema at the time, including -- in addition to Hoffman -- Michelle Williams, Catherine Keener, Jennifer Jason Leigh, Hope Davis and Dianne Wiest.
"It was incredible," Kaufman says. "Everybody I asked agreed to do it."
As for his star, Kaufman recalls Hoffman as being "a very hard worker. When we were in prep, it was very difficult to get in touch with him. And I remember my producer was very, very upset about this."
"But like his agent or his manager said, when Phil is working on a project, that's what he's working on. He doesn't do any other business. And it was true. When he came on to our set, that's all that he was doing for the amount of time that he was shooting that movie. He did nothing. He focused on Caden Cotard and this film," he recalls.