Kieran Culkin is an Oscar winner – Who would’ve thought? The child who made every heart melt with his adorable presence in Home Alone and pretty much everyone miserable as Roman Roy in Succession did it again in Jesse Eisenberg’s A Real Pain. With an incredibly moving performance that keeps the viewers hooked from minute 1, Culkin proves worthy of the belated Oscar.
![Kieran Culkin and Jesse Eisenberg in A Real Pain (2024) [Credit: Searchlight Pictures].](https://fwmedia.fandomwire.com/wp-content/uploads/2025/03/03133417/Kieran-Culkin-and-Jesse-Eisenberg-in-A-Real-Pain-2024-Credit-Searchlight-Pictures-1-1024x683.jpg "Jesse Eisenberg: Emma Stone “Blackmailed” Kieran Culkin Into Staying When He Almost Dropped Out of ‘A Real Pain’ 4")
However, if the 42-year-old had had his way, A Real Pain would have never materialized, and there would be no award season riddled with hilarious bits and speeches from Kieran Culkin as he blazes past one ceremony to the next. Diagnosed with a case of cold feet, the Succession actor refused to do the role – that is, until Emma Stone blackmailed him into getting back on board.
Jesse Eisenberg’s A Real Pain almost fell apart
![Kieran Culkin and Jesse Eisenberg in A Real Pain (2024) [Credit: Searchlight Pictures].](https://fwmedia.fandomwire.com/wp-content/uploads/2025/03/03133349/Kieran-Culkin-and-Jesse-Eisenberg-in-A-Real-Pain-2024-Credit-Searchlight-Pictures-1024x576.jpg "Jesse Eisenberg: Emma Stone “Blackmailed” Kieran Culkin Into Staying When He Almost Dropped Out of ‘A Real Pain’ 5")
Kieran Culkin really knows how to liven up a scene, but A Real Pain almost lost out on casting him as Benji when he decided to drop out of the movie.
It was one of the few scripts that made the 42-year-old actor laugh out loud while reading it, and he has been nothing but effusive of Jesse Eisenberg as a writer, director, and scene partner during this award season. However, given his audition process (or the lack thereof) and his sense of insecurity, Culkin thought better of his role and decided to drop out at the very last minute.
Emma Stone, who serves as an executive producer on the film (and also dated Culkin from 2010-11), got involved immediately and told him that although she understood and supported his decision to back out, the whole movie was going to fall apart without him. In an interview with AP, Culkin later admitted that Stone had used “reverse psychology” on him to get him to do the film.
Kieran Culkin was blackmailed into doing A Real Pain
![Kieran Culkin and Jesse Eisenberg in A Real Pain (2024) [Credit: Searchlight Pictures].](https://fwmedia.fandomwire.com/wp-content/uploads/2025/03/03133416/A-Real-Pain-2024-Credit-Searchlight-Pictures.jpg "Jesse Eisenberg: Emma Stone “Blackmailed” Kieran Culkin Into Staying When He Almost Dropped Out of ‘A Real Pain’ 6")
At the Palm Springs Film Festival, Jesse Eisenberg took to the stage after screening for a self-moderated Q&A session, during which he revealed the uphill battle to get A Real Pain on the road – both literally and figuratively.
Despite casting Kieran Culkin without auditioning him, the actor was the best choice to play Benji – as was proven by his sweeping win this award season. However, Culkin’s decision to drop out got Stone fired up in full producer mode as she scrambled to save Eisenberg’s film.
In the Q&A, the latter revealed (via Collider):
[Kieran] was trying to drop out of the movie two weeks before we were shooting. Like all the money had been spent, and he was trying to drop out in New York. So one of our producers, Emma Stone, essentially like blackmailed him to come back to the movie behind my back, and literally took him off the plane with his kids and flew to Poland with him.
I have a video of her holding his kid’s hands going through customs like a proof of life video that he made it.
Cast as Benji Kaplan, Kieran Culkin plays mismatched cousin to Jesse Eisenberg’s David Kaplan as the pair travel to Poland to learn more about their family history as they tour across Holocaust sites in the country and honor their grandmother. The film explores generational trauma and the impact of the Holocaust on American Jews.
The film won Kieran Culkin a Golden Globe, a Screen Actors’ Guild Award, a Critics’ Choice Award, and the Oscar for Best Supporting Actor in 2025.
A Real Pain is currently streaming on Hulu and is available to buy/rent on Prime Video and Apple TV.
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