After many years of radio silence on Elaine May’s Crackpot, a comedy starring Dakota Johnson that was planned to be the 92-year-old filmmaker’s fifth and final directorial feature, we finally got an update earlier this year. During the Madame Web press tour of all things, Johnson confirmed it’s still in development and they are working on casting. Now we have an update on an additional cast member and the one roadblock that’s preventing the film from getting underway.

Sebastian Stan, who now has A Different Man and The Apprentice in theaters, revealed on The Big Picture podcast that he’s attached to the film and what precisely is holding up production. “I have this thing, I don’t know if it’ll ever get going. I have this thing that Elaine May was going to direct. It was going to be her last film and her first film since Ishtar. It’s this crazy, kooky comedy,” Stan said. “It’s supposed to be with Dakota Johnson and myself. We’ve been trying to find a shadow director for Elaine May for the insurance company. So if anybody out there is hearing this and you want to fucking shadow Elaine May for her last film, let’s go do it! I mean, The Birdcage is one of my favorite fucking movies of all time and that’s totally a comedy in the [same vein] of When Harry Met Sally… and all that great stuff. So I’m all over it. It’s just, weirdly, some things come together and other things you wait for.

For those unfamiliar with a shadow or insurance director: it’s a common Hollywood practice for most aging filmmakers in case a health issue were to arise during production. In perhaps the most famous example, Paul Thomas Anderson acted as an insurance director by shadowing Robert Altman on 2006’s A Prairie Home Companion. Here’s hoping Stan’s wish can come true and we get to see one more May-directed feature.

In the meantime, for more on May, we caught up with Carrie Courogen, whose excellent book Miss May Does Not Exist: The Life and Work of Elaine May, Hollywood’s Hidden Genius recently arrived. Discussing what May’s career could have been post-Ishtar, she said, “She was a director mostly because it was a form of quality-control rather than having something specific visually that she wanted to communicate. It’s more like she had a script and she wanted to make sure the final version was as true to what she had on the page as possible. So I think she probably would have gone in the direction that her plays went in, almost always very focused on the same sort of themes of betrayal and relationships between two people. Mostly men and women. But they probably would have been smaller. I think Ishtar was a fun experiment. It was like a let’s-see-if-we-can-do-it-to-do-it sort of thing. I think she probably would have gone back to the realm of more independently shot films and smaller productions, more like Mikey and Nicky, more like The Heartbreak Kid. “

As we await more updates on Crackpot, listen to Sebastian Stan’s below.

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