'Escape at Dannemora' Finale: Ben Stiller on Tying Multiple Threads Together

Stiller also discusses which character was hardest to figure out and whether this story of criminal justice system failings has any political undercurrent.
Atushi Nishijima/Showtime

[This interview contains spoilers for the Sunday, Dec. 30, finale of Showtime's Escape at Dannemora.]

It's been nearly 25 years since the release of Reality Bites, Ben Stiller's iconic (for a certain generation) feature directing debut. That film had a running time of 99 minutes, which coincidentally is also the length of the seventh part of Escape at Dannemora, Stiller's debut as limited series TV director. 

Sunday's Escape at Dannemora finale brought the prison break drama full-circle, returning to newly liberated Richard Matt (Benicio del Toro) and David Sweat (Paul Dano) following last week's flashback detour and also bringing us back to Tilly Mitchell's (Patricia Arquette) conversations with investigator Catherine Leahy Scott (Bonnie Hunt) featured back in the premiere.

The episode is part wilderness thriller, part emotional resolution and part ongoing mystery as it hints at characters and motivations that we may never fully understand.

Stiller spoke with The Hollywood Reporter about why the finale lent itself to this expanded running time, finding the finale's different story beats, why Eric Lange's Lyle was the hardest character to get a read on and whether he'd direct a full eight-hour miniseries again.

The finale runs a whopping 99 minutes. Did you always know that it had to be told as basically this feature-length thing, or did that become clear as you were looking at it from above?

Yeah. It developed when the guys [Brett Johnson and Michael Tolkin] were writing the episodes and we were blocking it out, it was actually eight episodes originally. Seven and eight were going to be a two-parter, and really very early on in the writing as it was developing, we looked and we said, "This should just be its own movie." It just felt to me like every episode had to have its own vibe, and when I looked at the episodes, I feel like one and two go together, and then three and four go together, and then five is its own thing, and six is its own thing, and then seven has its own energy.

Also just the landscape and the scope and the fact that they're finally outside and they're finally in nature, and how that becomes their prison when they're out there, and how, especially for Matt, he just can't really survive out there. Yeah, very early on in the writing process, seven and eight just became one movie.

It feels as if this episode is three or four different things. It's sometimes a thriller. Then there's about a 20-minute stretch where there's no direct dialogue at all, which is remarkable. Then you've got Bonnie Hunt, who comes in and she cracks wise a couple times because she's awesome and she's Bonnie Hunt, but it's very much separate. How did you find the tone and form that fit in all of these elements that don't necessarily go together?

It was a challenge to figure out what it should be in terms of the telling of the story, because we knew that even with Catherine Leahy Scott, the Bonnie Hunt character, that as a person who was doing the investigation, she was never running the manhunt, so it felt to me that it would be very artificial to all of a sudden bring in some sort of a character that was the head of the New York State Police or whoever it was who was going to be the Javert or something going after them.

That didn't feel like that was organic, so we made the choice early on for them, out on the run, that we would try to tell their side of the story from their point of view. The idea was to be with Matt and to be with Sweat. You have the sense that there's a manhunt going on, which we see, and it's coming. Tilly can feel it, and we feel it through when we cut off of Tilly and Lyle at home. She feels like it's closing in and she can't get away from it. When we're out there, and it's obviously affecting the guys out there, too, but when we're with them, we're really in their world. As it gets closer to the end, we're just staying with them longer.

I just thought we should make the choice of feeling what it feels like to be captured from the person who's being hunted, from their point of view, because I didn't think we could introduce a character or a storyline that wouldn't make it feel like it was some sort of a procedural or something. And then it was about trying to find a way to interweave Tilly's story and Matt and Sweat's story, and I felt like it became about Tilly and Lyle and this detective who came to question her a few times, and how she ends up getting back to Catherine Leahy Scott, so it takes us back to the beginning of the show.

I'm curious about the shifting empathy/sympathy respect that you personally felt for Matt and for Sweat as you went along in this process, because it builds to a finale where there's no way Matt is going to look good out of this situation, but you do end in a position of begrudging respect for Sweat for staying with Matt and all of that.

We tried to go off of what actually happened and from what Sweat said in his interviews, and when you read the interviews that David Sweat did after he was captured, in the week after he was captured, he's very derisive and seems like he just didn't like Matt, and talks about how he slowed him down and how fat he was, and how basically he was a weight on him, and it was all his idea. This whole thing was all him.

When we talked to him last year, which is a couple years after they escaped, he had a very different feeling about [Matt]. At least when I talked to him, he was always smiling and laughing and talking about the funny things that happened to them when they were out in the woods, and when they were staying in the cabins. He told me little anecdotes about him, and said that he liked him and he was friends with him. It was this interesting juxtaposition of what I think he felt originally when he first got caught and in retrospect felt about him, which made me feel like he really did have some sort of a connection with him, but the reality was that Matt's drinking and his sickness really weighed him down.

I wanted to try to show that dynamic, and at the end of the day, these actors are playing these guys. You don't want to cheat it, and you don't want to make an audience feel for them anything they shouldn't feel other than what they're feeling. In other words, I don't want to tell the audience what to feel. The actors are going to give them a humanity. By episode six, I feel like we show who they are in terms of what they'd done, and then I wanted to just show them as two people who have a natural instinct to survive, and what that felt like, and what that must've felt like for them as individuals.

That's a fine line sometimes with how you score it and what you show, but I felt it was worth it to show with Matt that this guy had a last night, that he knew everybody was closing in on him. As an audience, I think you're invested on some level with him as a person, and it's worthwhile to show him as a human being, hopefully not trying to make you feel anything more than just the fact that he's a person who ultimately has had a very sad and broken life, and yes, did horrific things, too. I don't know. I'm not making any judgements, but I wanted the audience to have an emotional experience of them as people.

This story is obviously a very humane approach to the flaws of the criminal justice system, but do you see that as making it inherently political, or did you explicitly want to keep politics and advocacy off of the table?

It's not my job to be political in something like this. It's my job to try to tell a story that people get engaged in, and honestly, even telling the story, I never thought about the political aspect of it. It was more learning about what was going on up there and seeing the real place, and realizing that the texture and the environment of Clinton and Dannemora were such an important part of the story, because the reality is, these people are living in a very tough economic situation, having to work multiple jobs in a prison system that is very flawed and fucked up, I think.

Whether or not you think that's political or not, I just think that's my personal feeling. The reality is, if you talk to these people who work in this system, and that's one of the reasons why this happened, is the fact that a place like Clinton still exists and it's very antiquated and outdated, and the systems don't work. In terms of the people who are living up there, they're trying to make ends meet. The prison is a very important part of the economy up there. It's actually the only economy. There are multiple prisons within a 75-mile radius.

These people depend on these prisons, but yet the prisons are really flawed, so it's just part of the landscape of the story, and I think you couldn't tell the story without showing that. In that way, I feel like it's more an American story and saying a little bit about what's going on in our country right now more than anything else.

And I find it fascinating that by the end, Lyle is as close as this story might have to a heroic figure. How did your perspective on that character and his choices evolve?

Right. He, to me, is the toughest one to figure out. We never got a chance to talk to him. He didn't want to talk to us, which I understand. That's his prerogative, but I talked to people who knew, who know him, and the reality is that he made it clear that he did not believe any of the things they said about Tilly, and that he was waiting for her to come home.

You can look at it and say it's naive, and I think on one level it really is naive, but then you also have to think this guy has real feelings for her, and so we wanted to give him a sense of himself and try to reconcile that. For me, I wanted to reconcile that not as him just being a sad sack or a patsy, but as a person who actually had a conviction about how he felt and chose to stick with her.... We don't know how far she went in terms of wanting to have him killed or what she claims, which is that she didn't, but there's a lot of evidence that says she did.

They didn't have enough evidence to charge her, so there are a lot of unknowns there, but I think for Lyle, what we wanted to have in the story was a sense that this guy did have a conviction about how he felt as a person about her, and maybe he wasn't as much of a rube as you might think, and he actually had more of a spine than you might think. That was a choice we made. Ultimately, he ends up waiting for her. He says he's waiting for her, but who knows what really goes on between two people?

Having taken on this decision to direct every part of this, and talking about the complications of the production process, does it make you want to jump in and do another eight-hour series? Does it make you never want to do this ever, ever again?

I think one of the things that people have to understand when you talk about somebody directing one of these, directing all of the episodes on these things, is they're not shot like a regular series, where you shoot episode one, episode two, episode three, where you could actually bring in two directors and have one person leapfrog to the next episode. The way the production works, you have to make a choice that, if you're going to shoot something like this, that you have one director because you have to be able to shoot everything that goes on in the cell block, because you only have the cell block for six weeks. We were shooting from all the episodes, so you literally can't do it with multiple directors, unless you were shooting it like a series where you shot it in order, which would be almost impossible to do for production.

To me, it was more about just being excited about telling the story and really, if it had been a movie, if it had been a five-part series, a ten-part series or a seven-part series, I felt like it was a story that I wanted to tell as a director. Honestly, there are not that many stories with this kind of tone that are being made as movies, and I thought that the story deserved to be told in this format. But at the end of the day, in terms of the world of movies, there are just not that many interesting movies being made that have this tone. You have a much bigger canvas to play with in television with something like this, so I really had a great time. Definitely challenging, I'd probably do it a little bit differently, take a break sometime in the middle of shooting, which of course I never want to do, but the shoot went on for so long and that was probably the toughest part of it.

But just to have a chance to tell the story is what I felt very fortunate to be able to do.