'Escape at Dannemora' Director Ben Stiller on Filming in a Real Prison and Developing Trust With the Community

Escape at Dannemora S01E05 Still - Publicity - H 2019
Wilson Webb/SHOWTIME

Showtime's drama meticulously re-creates the events that led to the infamous escape of two inmates aided by the correctional facility's seamstress.

With a true story as unbelievable as Showtime's Escape at Dannemora, Ben Stiller wanted to leave little to the imagination. When presented with a spec script by Brett Johnson and Michael Tolkin, he originally turned down the project because it lacked the necessary details to tell the story of two inmates who escaped upstate New York's Clinton Correctional Facility with the help of a prison seamstress. Everything changed when New York State's inspector general released a 150-page report that provided Stiller with the particulars he needed to commit. 

THR spoke with the 53-year-old executive producer/director about the intensive research process and how he received permission to shoot at the real prison.

Could you have done this project without the inspector general's report?

It was integral because the first scripts they wrote were an imagining of what happened. They didn't have that much information, and I initially passed because I felt I didn't know enough about what went on. That report had all of those details of how this relationship developed between this woman, these two inmates and how they were able to escape. Researching it went on for about a year.

When producing a true story, does the pressure of accuracy weigh on you at all times?

It does. Ironically, we find that what people actually do is sometimes more fantastic than something you could make up. The fact that it's true is what's so interesting about it. I made every attempt to find out what really happened and tell the story as accurately as possible.

How did you end up shooting at Clinton Correctional Facility?

The New York State Department of Corrections allowed us access through a meeting we had with New York State Gov. Andrew Cuomo. We didn't think we were ever going to get it, but luckily, we got to film in some of those places where all this happened.

Because the escape humiliated Dannemora, how did you assure locals that they'd be respected?

Some people were definitely a bit wary because when the escape happened, Dannemora was descended upon by the media for about a month — and then everybody left. So I felt it was important that we developed trust and let them know that we were trying to tell the story as truthfully as possible. We made some really good friends there, such as ex-corrections officers and people in law enforcement. We worked with all locals at locations where things actually happened. That made a big difference, especially in re-creating the manhunt.

Was episode five's tracking shot the most difficult to produce?

Definitely. The inspiration for the shot was GoPro footage that law enforcement made a few days after the escape, where they retraced Sweat's escape. We pulled that shot off across our entire seven-month shoot in Dannemora, New York City, Yonkers, Pittsburgh — wherever we could find tunnel sections.

Is there another nominee that you're looking forward to meeting at the ceremony?

I'm looking forward to crossing paths with the Game of Thrones people. I was also really taken by Chernobyl.

Interview edited for length and clarity.

This story first appeared in an August stand-alone issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.