Ben Stiller Unlocks An 'Old-Fashioned' Prison Break In 'Escape At Dannemora'

TERRY GROSS: This is FRESH AIR. I'm Terry Gross. Our next guest, Ben Stiller, is nominated for an Emmy for directing the Showtime series "Escape At Dannemora." The series is nominated for 12 Emmys. Stiller is best known for his work acting in and directing film comedies and recently for playing Michael Cohen on "Saturday Night Live." "Escape From Dannemora" (ph) is a change in direction. The seven-part series is based on the true story of two inmates who escaped from a maximum-security prison in upstate New York in 2015. The series isn't just about planning and executing the escape. It's also a character study of those two inmates and the prison employee who helped them escape.

Both inmates, Richard Matt played by Benicio Del Toro and David Sweat played by Paul Dano, worked at the prison tailor shop where prison uniforms were made. They convinced the civilian employee who ran the shop, Joyce "Tilly" Mitchell, to get them the tools they used to escape by digging through the basement walls and steam pipes of the old prison. The two prisoners were able to manipulate her through sexual relationships with her. They told her they wanted to be with her after they escaped. What they really wanted was for her to be with them just long enough to drive the getaway car and get them to a safe place. She's played by Patricia Arquette, who's also nominated for an Emmy. We'll hear from her a little later.

The series opens with Arquette's character Joyce "Tilly" Mitchell in jail, this time as an inmate, not an employee. She's being questioned by the New York state inspector general who's investigating the escape. The inspector general is played by Bonnie Hunt.

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BONNIE HUNT: (As Catherine Scott) Nice to meet you, Joyce.

PATRICIA ARQUETTE: (As Joyce "Tilly" Mitchell) Everybody calls me Tilly.

HUNT: (As Catherine Scott) Tilly it is.

ARQUETTE: (As Joyce "Tilly" Mitchell) Joyce is my mother's name. When you call me Joyce, I feel like you're talking to my mother.

HUNT: (As Catherine Scott) Is your mom still with us?

Oh, good. I love knowing my mom's just a phone call away.

ARQUETTE: (As Joyce "Tilly" Mitchell) I already talked to the cops.

HUNT: (As Catherine Scott) Four times in seven days, I understand.

ARQUETTE: (As Joyce "Tilly" Mitchell) Yeah. So what is this?

HUNT: (As Catherine Scott) Let's not get into any details until the stenographer gets here. I mean, even though it's all taped, it's actually more accurate. This girl, especially - she's been with me 15 years. I did a comparison, and I was right.

ARQUETTE: (As Joyce "Tilly" Mitchell) Are you with the state police?

ARQUETTE: (As Catherine Scott) Please - no, I'm the inspector general for the state of New York.

ARQUETTE: (As Joyce "Tilly" Mitchell) Oh, so the post office?

HUNT: (As Catherine Scott) No, the post office is federal. I'm state. So if there's any corruption in the state agency, it's my job to find it and stop it, whether it's a state park or the Port Authority, and I report directly to the governor.

ARQUETTE: (As Joyce "Tilly" Mitchell) Am I going to lose my job?

HUNT: (As Catherine Scott) Should you?

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GROSS: Ben Stiller, welcome to FRESH AIR. And congratulations on "Escape At Dannemora." You were able to actually shoot at Clinton Correctional Facility in Dannemora, where the story is set. Did you have any protection when you were shooting in there? Did you feel like you needed any? Did the correctional facility feel like you needed any?

BEN STILLER: The first trip that we took in there, we got ushered into a little trailer that - sort of a permanent trailer. They had set up a meeting room in there. And the superintendent and the deputy superintendent and a bunch of people who were administrators at the prison gave us a talk and told us what we were going to be doing and the tour we were going to be taking and basically said this is a dangerous environment. They were going to do everything they could to keep us safe and keep things as low-key as possible. But the reality is, you know, you're in a prison. So you don't know what could happen.

And they tried to walk us through spaces at times when prisoners weren't there in the spaces. So, like, we were actually ushered into sort of this small, little office area when you first walk in where the corrections officers can lock themselves in to, you know, turn on lights and things like that. And because the timing was off, they had all - there were probably about 12 of us from the crew - we all kind of jammed into that little office while they let the inmates go out for lunch because we were - they were behind schedule. And that was a really strange experience because (laughter), you know, we're all jammed into this little office. And then, you know, the inmates were looking at us. We were looking at them.

And you know, they're human beings. They're people. But, you know, I'm sure they had their thoughts about - what are we - you know, what are these visitors up to? And then you just see, you know, the reality of life for these people, which is regimented. And it's - and obviously, they're all there for a reason. But as - you know, in terms of, like, the human condition of it, it's pretty heavy.

GROSS: You did meet with David Sweat, the survivor of the two inmates. He's the one who's played by Paul Dano. So he had, on July 4 - I forget what year it was - July 4...

STILLER: 2002.

GROSS: Thank you. He and some friends had robbed a fireworks - was it a fireworks and munitions store?

STILLER: Yes, I think it was a fireworks and gun store - something.

GROSS: And so they stole a lot of stuff, and they're going through what they got when a police car - well, it was actually a deputy sheriff - pulls up.

STILLER: Right.

GROSS: And do you want to describe the crime? It's pretty horrible.

STILLER: Yeah. I mean, it is. It is. They were a bunch of teenagers. I think he was - I'm not sure how old he was - maybe 20 or something like that. And he'd already had a record and had been in detention before. And they had, yeah, robbed this store, and they were transferring these guns from a pickup truck into his car or the other way around.

And this deputy was on patrol in Broome County, N.Y. He just happened upon seeing them in this parking lot. He saw something was going on, and he pulled into the parking lot. And he got out of the car, started to draw his weapon and, you know - and announced that he was police. And David Sweat shot him, I think, 13 times and then ran him over with his car. And then his friend came over and picked up the officer's gun and shot him two more times. And that's - you know, that's what he did to be sentenced to life imprisonment.

GROSS: And the really - I mean, it's absolutely horrible that he shot this deputy sheriff. The fact that after shooting him 13 times, then he gets - then the killer gets in a car and runs him over. That's just twisted. I mean, that's just sadistic and twisted. And here you were talking to him.

STILLER: Yeah.

GROSS: So how much of that did you keep in your mind? How much of it did you try to block out while you were talking to him and trying to get as much information and insight from him as you could?

STILLER: You know - well, to me, that's what the interesting thing is about incarceration and kind of this story that we're telling and how people act in life. And they can do a horrible thing, and then life goes on. And then, you know, they're - and they act normally or they, you know, are not - you know, they don't act like a monster. So if I'm just being totally honest, it was easy for me in the moment with him to let that go as I was asking him details of the escape.

I'm not saying that's a good thing, you know? It's not something I'm proud of, but the - so as I learned more about what he had actually done - and actually, when we filmed the scene, to, you know, have a small feeling of what that reality was and what happened - it actually, you know, it affected me much more. And then as the reality of the show came on the air and the fact that the officer's relatives were going to see this - you know, all of that brought it much more home to me. And I just say that in that it's - trying to, like, illustrate that I think it's easy sometimes for human beings to disconnect, and I think I was probably a little guilty of that when I was sitting across from him.

GROSS: Let's talk about the crime that landed the other escapee in prison for murder, and that's Richard Matt, who's played by Benicio Del Toro in the series - and oh, man, talk about gruesome.

STILLER: Yeah.

GROSS: He killed his former boss. I have to confess, I had trouble watching the scenes of the murder and torture, so I'd like to know how far you wanted to go with it because you really - I know you really want to convey the horror of this crime, the brutality of this person who you might have had some sympathy for in previous episodes because you don't show the murders till the end of the series. So you had a lot of decisions to make about how detailed to show the murder and the torture.

STILLER: Yeah. I mean, it's sort of a judgment call. It came down more as we were editing it. It got less and less in terms of what we saw. But it's very brutal and, I mean, the intention behind it was, hopefully, as an audience, you, you know, are jarred because you've developed this sort of - I don't know - impression of who these guys are based on who they've been for the last five hours of the series, who were just guys in prison trying to get out, which is what your experience would be of them if you met them the way I met David Sweat - as a guy just sitting there across me. But the reality is that they did these brutal crimes, so that's why I felt it was important to have it be shocking and brutal as a viewer after sort of being lulled into the reality of who they were now.

GROSS: If you're just joining us, my guest is Ben Stiller. He directed the seven-part Showtime series "Escape At Dannemora," which is nominated for 12 Emmys. We'll be right back after a short break. This is FRESH AIR.

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GROSS: This is FRESH AIR. Let's get back to my interview with Ben Stiller. He directed the seven-part Showtime series "Escape At Dannemora," which is nominated for 12 Emmys. It's based on the true story of two murderers who escaped from Clinton Correctional Facility in upstate New York in 2015.

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GROSS: So one of the ways they escaped is that David Sweat found this, like, giant hot water pipe that was turned off for the summer. He cut a hole in that, crawled out of that. It led to a manhole cover that he was able to open, and that's what ultimately led them to escape. Did you literally shoot in that pipe?

STILLER: (Laughter) Well, we shot in a pipe. We shot in an 18-inch pipe, which is what they were in, but it wasn't that pipe. But we basically recreated the set based on the actual dimensions of the area that they were where they got to that. They basically - he went down through that catwalk, got down into the bowels of the prison and found his way underneath all the buildings to the outer wall - the base of the outer wall of the prison. And there, in that - going into that outer wall was a steam pipe that was coming from the power plant that was about - I don't know - a thousand feet away from the prison. So he knew that that steam pipe led to the power plant, but this wall was in the way, and it was a seven-foot thick wall.

So we recreated that pipe and that area where the outer wall was where he did all the cutting, and then we found locations. We found a prison in Pittsburgh that was about 150 years old, even older than Clinton, and we shot in the actual underground area of that prison. And we also shot in waste treatment facility tunnels in Yonkers, New York, and then we also built pipe sections also. So it was a combination of all those.

GROSS: So some of your shoot was at Clinton Correctional Facility, where the story actually happened. You were first denied permission. Then you got a personal meeting with Governor Andrew Cuomo, and he gave you permission. What did you have to do to convince him that this wasn't going to be another version of "Oz"?

STILLER: I didn't have to do anything. I mean, we reached out, and I talked to his chief of staff, and she talked to him. And we told her - I told her what we were doing because we weren't able to get access to any prisons in New York, and I felt that as the governor and the New York State Film Commission, they would want us to have at least a chance to shoot more of the show in New York just for, you know, the revenue and for - since it's a New York story. And so I think that was part of it, and he was like, yeah, we want you guys to be telling the story here and bringing the business to New York. And he was also really fascinated by the story, so when I talked to her, she got us in touch with the Department of Corrections. And I think they talked to them and asked them to be helpful to us, and they said they would open up the manhole for us and let us shoot outside the prison.

And then he said, do you want to have a meeting? Because I'd like to hear what you're doing. And so I sat and talked with him, and he wasn't in any way questioning me as to what we were - you know, what was going to be in the story. He never once asked to see the script or make sure that they approved of what we were doing. He purely wanted to, I think, just hear what I was interested in in the story, and then - yeah. At the end of the meeting, he said, well, what can we do to help you? And that was the moment where I (laughter) - I was thinking of, like, the hundred people back at the production office who were - you know, we didn't have a location. And I was like, well, can we shoot at the prison? And he looked at his chief of staff. He said, well, you got to shoot at the prison, right? (Laughter) And I was very happy. But really, the fact that they allowed us to shoot - like, any of those scenes where Tilly and Lyle are going to work, and you see people going in and out of the prison or even just shooting the prison itself and the manhole - that they unsealed the actual manhole for us and the...

GROSS: During the escape - oh, so you filmed the escape with the real manhole.

STILLER: We filmed him - when he comes - when they come out of the manhole, that's the actual manhole. And that's the actual street, and that's the actual - that's basically what happened when they came out of the manhole in episode five when they walk around the block and decide to walk down the street and, you know, have a cigarette. That - that's, you know, according to Sweat, exactly what happened. And that's the place it happened in.

GROSS: So Patricia Arquette gained around 40 pounds to play the prison employee. And what issues does that create for you as a director? Because there was also, you know, the scenes that are shot when she's in prison or jail. And so her weight changes depending on what the time is that you're shooting.

STILLER: Right.

GROSS: So it takes time to gain weight, and it takes time to lose weight. So just as the director in that situation, as opposed to being the person who has to eat a lot or stop eating (laughter), what are the issues that you have to deal with?

STILLER: Well, I was concerned about it, first of all, because the shoot was so long. The shoot was eight months long. And I really felt like she needed to gain the weight to - you know, you can't just wear a sort of, you know, suit to make you look heavier. You know, it changes her face and all that. And she was also wearing teeth and contact lenses to make her eyes brown because she has these piercing blue eyes. And so it was a whole bunch of things.

But the weight was really, really important, I felt, because she has such - you know, she's a very classically beautiful woman who has these movie star looks, and it was just trying to sort of get away from that for this character. And it was tough because I kept on encouraging her to (laughter) eat. So - and Paul Dano was working out with a weight coach because he - he's, you know, not as built as David Sweat was because David Sweat built up in prison because he was afraid of getting beaten up. So all of them had to commit to changing their bodies.

GROSS: Well, Ben Stiller, it's been great to talk with you. Thank you so much.

STILLER: Thank you.

GROSS: My interview with Ben Stiller was recorded in January. He's nominated for an Emmy for directing the seven-part Showtime series "Escape At Dannemora." The series has a total of 12 nominations, including one for Patricia Arquette, who's nominated for her performance in this series. We'll hear from Arquette after a short break. This is FRESH AIR.

(SOUNDBITE OF MUSIC) Transcript provided by NPR, Copyright NPR.