Ben Stiller On Directing 'Escape At Dannemora,' Nominated For 12 Emmys

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Ben Stiller arrives at the 71st annual DGA Awards at the Ray Dolby Ballroom on Saturday, Feb. 2, 2019, in Los Angeles. (Chris Pizzello/Invision/AP)
Ben Stiller arrives at the 71st annual DGA Awards at the Ray Dolby Ballroom on Saturday, Feb. 2, 2019, in Los Angeles. (Chris Pizzello/Invision/AP)

The Showtime limited series "Escape at Dannemora" tells the true story of how two inmates escaped from a prison in upstate New York in 2015.

The seven-episode series stars Benicio Del Toro and Paul Dano as the inmates Richard Matt and David Sweat, and Patricia Arquette as Joyce "Tilly" Mitchell, the prison employee who helped them break out of the prison. The series, which is directed and executive produced by actor Ben Stiller, was nominated for 12 Emmy Awards.

Stiller says what drew him to the story was how “fantastic” it was that these events happened. Matt and Sweat, who were both in prison for murder, escaped the Clinton Correctional Facility by digging a tunnel out with tools given to them by prison employees. Almost three weeks after their escape, Matt was shot and killed by U.S. Border Patrol agents and a couple days later, Sweat was captured by a state trooper.

“I was very curious about how something like this could actually happen,” Stiller says. “And as we learn more about it and the human relationships that were going on in that prison between the people who work there and the inmates, that to me was really fascinating.”

Staying true to the story was very important to Stiller, who says he wanted to portray just how horrible the conditions in the prison were that led the two inmates to escape.

“To actually see what the day-to-day life was in there, especially for these two inmates, was important, I think, so you could sort of get why they were working so hard to get out,” he says. “But then also we wanted to let the audience know what they did to get in there so that if you are rooting for them, you're going to be hopefully a little confused as to why you're rooting for them.”

Interview Highlights 

On the importance of accuracy 

“It was important to me only because I didn't know a lot about this world, and I felt a little bit scared I was gonna get it wrong. So I really kept on going back to what actually happened, and I thought, 'Why not just try to just tell the story as realistically as possible?' Because I think we've seen a lot of prison escape movies or television shows, and what's interesting to me about this one is that it actually happened. It's a real story. So how does that actually happen? What are the steps that occur? How do the relationships form? And who helped who, and how do you actually cut your way out of a cell in 2015 without anybody knowing?”

On how prisoners and employees reacted to filming at Clinton Correctional 

“I didn't have a chance to interact with the prisoners as much. We went into the tailor shop where Tilly Mitchell, who Patricia Arquette plays, worked and the two inmates worked, and she was a civilian supervisor. So we went through that tailor shop, and I think for them, it was probably a little bit inconvenient that we were filming there. I think for the corrections officers there they were concerned about how we were going to portray the story. I think there were mixed feelings going in there with us.”

On what he learned about prison life 

“One of the biggest things that just hit me at first was just how heavy and oppressive the feeling was in the prison and that prison has been there, Clinton Correctional, has been there for over 100 years, and you feel the weight of it. As I got to know the people who were working there and the systems that are in place there, I learned a lot about what's not working in the prison system, which we know I think, if you're aware of what's going on in our country, we know that the prison system is flawed. But what I learned was that the corrections officers who work in these prisons are not motivated to really necessarily take chances that they would have to to do their jobs really well because of how dangerous it is, and there's a sort of generational complacency that has happened in some of these prisons because people have worked there for years and years at very low pay. And there's not a lot of incentive to put yourself on the line. Then you see just how tough it is for the inmates too.

“You get that feeling like this isn't really helping people though, you know, it's obviously a necessary thing. So that was part of, I think for us, telling this story was trying to show that ecosystem that exists in there and how all of those factors contributed to the escape.”

On if Matt and Sweat could have broken out without help from prison employees

“No. I mean, they needed to get the tools smuggled in and they needed access. There are things that just happen in the everyday life of the prison like being allowed to go in the catwalks to fix electrical circuitry if there's an inmate who does that well, or in Richard Matt's case to hide his paints because he had a relationship with Gene Palmer, who was one of the corrections officers who he would give paintings to. So there was this sort of barter relationship and that type of thing goes on all the time in prisons. It doesn't necessarily always lead to an escape. And the same thing in terms of physical relations between prisoners and prison workers — that happens all the time. I talked to somebody at Clinton who told me that what happened between Tilly and Richard Matt and David Sweat having sexual relations, it happened many many times at Clinton over the last 20 years that he was aware of. It just never was really brought out because there wasn't an escape that it resulted in.”

On how this series is a departure from his comedic background

“I don't know if it's my comedic background as much as I was just always wanting to make movies. Since I was nine or 10 years old I knew I wanted to be a director, and the movies that I grew up watching were dramas and comedies. And you know in the ‘70s, the genres were a little less well-defined. I think there were movies that were very serious that had humor in them, and then a lot of the comedies were a lot more edgy and realistic. That kind of thing … influenced me a lot. The movies I think you see when you're a kid really stick with you, so I think that's what it was more than anything.”

On what he enjoys about directing compared to acting 

“I would say that I might like [directing] more actually. I love acting and I love the experience of it, but it's a very very specific thing that I feel like you're constantly trying to figure it out. But as a director what I enjoy is that you kind of have a sense of what you want the thing to be, and then things happen within it that are totally different than you ever imagined. But having that sort of point of view about the creative project to me, I think I do enjoy that more, and I love the collaboration of working with actors. I love watching actors work and having a chance to maybe collaborate with them in some way to bring out their best and let them have the freedom to do their thing.”

Julia Corcoran produced and edited this interview for broadcast with Todd Mundt. Samantha Raphelson adapted it for the web. 

This segment aired on August 13, 2019.

Jeremy Hobson Former Co-Host, Here & Now
Before coming to WBUR to co-host Here & Now, Jeremy Hobson hosted the Marketplace Morning Report, a daily business news program with an audience of more than six million.



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