Ben Stiller on 'Escape at Dannemora' Flashbacks: "The Hope Was to Punch You in the Stomach"

Ben Stiller, who directed all seven 'Escape at Dannemora' episodes for Showtime, also discusses the method to Benicio del Toro's madness.
Wilson Webb/Showtime

[This interview contains spoilers for the Sunday, Dec. 23, episode of Escape at Dannemora.]

Last week's episode of Showtime's Escape at Dannemora was a breathlessly paced hour focusing on the escape that gives the show its title.

Viewers tuning in to Sunday night's episode expecting to see convicts Richard Matt (Benicio del Toro) and David Sweat (Paul Dano) interacting with the outside world got what they wanted, but not in the way they expected. The season's sixth episode took a step back and showed viewers the crimes that got Matt and Sweat thrown behind bars in the first place, also flashing back to a key moment in Tilly (Patricia Arquette) and Lyle's (Eric Lange) relationship.

Ben Stiller, who directed all seven Escape at Dannemora episodes, spoke with The Hollywood Reporter about this dramatic change of pace, the decision to hold back on violence until this episode and why Benicio del Toro's acting choices can be both terrifying and also grounded.

The Q&A follows.

This episode, as much as it's about the characters, I feel like it's at least as much about the audience and the assumptions that we've made over the first five episodes about these characters and our instinctive desire to root for them to escape. Do you want us to feel guilty, uncomfortable?

I'm hoping that it catches you by surprise, and that you're not expecting this. It's definitely a misdirect, and we're taking advantage of that moment where people are naturally going to be rooting for them to get out, because they're the protagonists even though they're these bad guys. You can't help but root for the guys getting out on some level, and I think intellectually, the audience knows they're bad guys, but the hope was to punch you in the stomach a little bit and really confuse you.

That's beside the fact of actually having this misdirect, for the first 10 minutes of the episode, that you really would not know what you're looking at, and then when you see that, it would jar you and then hopefully confuse you as an audience, because that's how I feel when I think about these guys. I'm amazed at what David Sweat did, the engineering feat, the technical ability he had to get out, but he also was in prison for murder.

You think about these guys and you think, "Well, of course I'd want to get out of jail if I was in there too," but who are these people? What's the reality? Are they people that are worthy of any sympathy at all because they're human beings? That's what I think is fun as an audience to experience and not be told what to feel.

I'm curious where it fit in the production schedule and how it felt different from the episodes that went chronologically.

We had a very strange production schedule on this show. By the time it all got together and we were ready to shoot, we had to start shooting in late August, we had to capture the last episode, really basically everything in the Adirondacks, before the leaves turned, so we start shooting the whole thing backwards, and then finally ended in the winter to shoot most of the exteriors for the first episode.

Then we shot basically a movie schedule where we shot everything that we would shoot for the whole show in one location. The flashback episode was the outlier in terms of really trying to figure out how to plan it because of the logistics of it being so outside of everything else, and the weather and all that, so it was actually spaced across the entire shoot. But in segments, so actually the Sweat/[Deputy] Tarsia segment, the first one, was actually the first one we shot, and we shot that very early on in the schedule, probably I think the second or third week of shooting the whole show. We shot it up in Plattsburgh, even though that's not where it took place, because that's where we were, so that was the first one.

Then the Matt one was way at the end of our initial production shoot. I think it was actually mid-March. It was very cold. It was the last stuff that Benicio shot, and we did that all in the outlying area of New York City.

And then the Tilly flashback was the following June, because we had shut down production. We really just were so wiped out by the end of production that we made a decision just to end the main shoot, give Patricia some time to lose some weight from what she'd gained for the show, for the flashback, and also just do a stripped-down crew and shoot it very differently. We shot it on 16mm and had a different approach for the Tilly flashback, just because of the feeling we wanted to have, so that was in June. I'd been editing for about three or two and a half months when we shot that one.

How do the actors respond when you tell them that this episode, which is so pivotal and gives so much of their backstory, is going to have to be shot in this out-of-sequence and even piecemeal way?

They were really excited. They loved it. [Laughs.] As much as they loved us basically saying, "Hey, it's going to be an eight-month shoot." Honestly, I didn't tell them that, because I didn't know it was going to be an eight-month shoot in the beginning. I thought it was going to be quicker, but we went a little longer than we thought, because it just ended up needing that.

I'll tell you, Patricia really was behind the idea of doing it separately. I think it was really good for her and for Eric [Lange] too, because Eric lost a bunch of weight, too, because he had gained weight for his character. I think to have just a fresh start on it, for them, that was really positive. The Sweat one is mainly not Sweat, it's Jim Parrack, who's a really good actor, playing Tarsia and it was like making our own little movie there with him.

Then with Benicio, it was as challenging as anything else in that these actors had to jump back and forth sometimes between episodes within the day when we were shooting on the cell block, which I think was more challenging.

We had this dream that we're going to shoot everything in continuity on the cell block, everything from episode one, everything from episode two, and it just didn't work out that way, because for all different reasons, like set dressing or we had a crane one day that we needed to use for a shot on the catwalk. So they had to jump back and forth between episodes a lot, and that was, I think, more challenging. But I think once we were into the mode of, "OK, for the next three days, we're doing the Matt flashback," at least they could get a momentum going there.

Benicio is utterly terrifying in this episode. How much did this episode represent letting him off the leash entirely?

Well, he's had more experience playing characters like this and doing sequences like this than I have as a director for sure, and so I was following his lead in terms of how he wanted to approach it, having to get into the mode of playing this guy. It was really interesting for me to work with him on that process, because I feel like he had a very clear idea going in of trying to figure out a way to make each scene interesting for an audience, but also as a character, trying to find a way into it that told you something about the guy.

He felt very strongly, as I did, that this was where you had to see who this guy really was and why he was in prison, and because it's one of the least violent prison stories probably ever, on our show, in terms of what actually happens in the prison. There's no stabbings. There's a little scuffle at one point in episode two, but at one point, we had written in showing Matt being more violent in the yard in an early episode, and Benicio suggested holding off on that and not showing any violence from Matt until this episode, which I thought was a really great idea, and a brave idea, too, because you had to trust that he would be intimidating enough without seeing him actually do anything that's violent, just in terms of who he is and how people react to him.

I think it pays off for his character, because you get lulled into being fascinated with this guy who is intimidating, but then you actually see what he is capable of very deep into the show, and so that was, I thought, an interesting choice and idea that he had.

The thing I like so much about the performance is that 95 percent, it's smooth and slick and understated. Then every once in a while, the crazy bursts out, like his threat to Tilly in the backroom or the crazy laughing, post-escape. From your perspective behind the camera, what is your reaction when you see moments like that come out?

That's what's interesting about an actor like Benicio, where he's going to make a choice like that and have the courage to stick with that and to go with it. As a director, I'm looking at it and I'm trying to synthesize it and go, "OK, well.… You're going to do that choice? There's also the way of just doing it a lot more normally, too." What I found with Benicio was that there was always a logic for him in how he was approaching something, and for me, it was my job as a director give him the feedback on it.

We would talk about where it made sense to go for something and where to try something, and then also in editing, you always have those options. What was so interesting to me about that moment was it's very clear the moment before, when she laughs it off when he tells her, "Five years," and she doesn't take him seriously, that he in that moment realizes that he made a mistake in telling her and his next impulse is to scare the shit out of her. To me, that's his logic there in that moment, so even though it's this crazy moment, there's a logic to it. But that's Benicio. That's what's so great about him as an actor. It's never arbitrary. It's motivated, but it's very brave in terms of the choices.

Given that, as you say, Sweat is in prison for murder, but continues to insist that he didn't murder the cop himself, how do you approach what is "true" about these guys and their backstories versus the version of the truth that you want to tell here in the story?

I think there's pretty much of an accepted truth that he was convicted of that murder and that it happened. I've not talked to him in depth about why he feels he was wrongly convicted, but I think it has to do with the fact that, while he shot that officer multiple times, his friend also shot him a couple of times, and so in some way, he feels that he's not solely responsible for it or responsible for his death, which is hard to believe. The reality is that that happened and he did that. He did shoot that guy, and that officer was just doing his job, so it's a horrible crime.

I think that you have to just try to tell it in as real a way as possible based on what we all know, and in terms of him as a character, I wanted to show his reality of how he feels about it. You just have so much real estate to be able to tell those aspects of the story, so you just make those choices when you're making the show of what you're going to show people. Hopefully it's enough that people can then ask those questions themselves or get more information if they want, but hopefully it's a fair assessment of what happened.