Ben Stiller Discusses Prison Parallels Between 'Severance' and 'Escape at Dannemora'

Ben Stiller does a deep dive into his directing catalog to discuss 'Severance,' 'Escape at Dannemora,' and 'The Secret Life of Walter Mitty' with Metacritic.
by Erin Qualey — 

Ben Stiller

Angela Weiss / Getty Images

When Ben Stiller was 14 years old, he had a subscription to American Cinematographer magazine. Growing up in a household with two hardworking comedy legends — Anne Meara and Jerry Stiller — as his parents, the glitz of the entertainment world was an ever-present part of his childhood. From a young age, Stiller knew he wanted to tell stories, but he also knew that those stories had to make quite the journey from page to screen. And he kept finding himself fascinated by the how. 

He began acting professionally in the late 1980s and just a few years later, starting in 1992 with The Ben Stiller Show, Stiller became a fixture behind the camera as well. Soon after his foray into TV, Stiller capably directed the poignant dramedy Reality Bites in 1994, followed by the cult classic The Cable Guy in 1996. He seemed drawn to telling unique, clever, and memorable stories that broke barriers and drummed up fascinating lines of conversation. 

Over the decades, Stiller has become one of the most recognizable faces in Hollywood. He's best known for such riotously funny fare as Tropic Thunder and Zoolander, but viewers are often surprised to find out that he's also a well-established director. 

"If you're lucky enough to have a career as an actor where people identify you as something, it's not surprising to me that most people would just know me in that one way," Stiller tells Metacritic. "If people are enjoying it and are really wanting to watch it, that's ultimately what I want."

It looks like Stiller is getting his wish. Recently, Twitter has been abuzz with viewers discovering that Stiller is the director of Severance, the critically-acclaimed (Metascore: 83), mind-bending series airing on Apple TV+. But Stiller has been refining his dramatic directing chops for the better part of a decade. 

Here, Stiller takes a deep dive into his directing career with Metacritic, reflecting on three recent, dramatic projects, including the escapist allegory The Secret Life of Walter Mitty (2013), the gutting prison-break drama Escape at Dannemora (2018), and the compelling and mysterious Severance (2022). 

The Secret Life of Walter Mitty was a departure from the straight up comedies you had been directing throughout the 2000s. The script for the film notoriously bounced around in development before you were able to stick the landing. What made you want to tell this story in particular? 

I just thought it was a beautifully written script, and [screenwriter] Steve Conrad has such a unique voice. He took that story and totally reinvented it. We started to collaborate on it when I came on board, and we spent a few months together adjusting things in the script and looking at it, trying to think about it through the lens of me doing it, and we had such a good time working together on it. I felt like we were doing something together that I don't think either of us would do separately. It was so evocative to me, the imagery in it, and the feeling behind the imagery as well. I remember him telling me that when he was writing the early draft of the script that he walked around for weeks and weeks in Chicago trying to figure out what was that picture, what was that amazing, final image. And the hard work that he put in, that he really wanted to put together an experience for an audience that was special — I know that sounds obvious, like doesn't everybody, but he really cares about that. For me, when I'm working with a writer, it can't be, "Here's a script, now go shoot it"; it's really collaborating and connecting.

It's really interesting that you mention collaboration because collaboration is a commonality between all three of these projects we're discussing today. You worked with Theodore Shapiro on music and Sarah Edwards in costuming on Walter Mitty, and Jessica Lee Gagné in cinematography for Escape at Dannemora, and you brought them all back to work with you on Severance. What does it mean to you to build this cohesive team of creatives that you can collaborate with whenever you embark on a new project? 

It's so important. There's a comfortability when you work with people you've worked with before and also a trust factor. I feel that directing is such a collaborative thing because you have to rely on working with people who are very good at the things that they do. There are brilliant filmmakers like Steven Soderbergh, who I'm just amazed at, who will go write and edit and shoot. What an incredible responsibility! And, for me, I get so excited to work with an amazing artist such as a cinematographer or a costume designer or an editor or a composer. [Composer] Teddy [Shapiro] and I go way back to Tropic Thunder and there's a collaboration aspect in him not saying, "This is it." Instead, he'll say, "How do you feel about this?" And then he'll come back with something else. That's a theme for me, being able to have that back and forth with somebody. I can't write a note of music, but when I hear something that he writes that in some way affects me or moves me, it's amazing.

Patricia Arquette is another individual you continue to collaborate with. Most recently, she played the real-life Joyce "Tilly" Mitchell in Escape at Dannemora and now she's in Severance as Harmony Cobell.

She's just the most incredible person. When I think of her, I think of generosity of spirit. Aside from her talent, but it's tied into who she is as a person, she's fearless in what she puts out there and she's willing to take chances and will say what she doesn't know. I think that any person who's in a position of trying to do something creative, sometimes you don't know and you just have to take that chance. We hadn't really connected since we did Flirting with Disaster for a long time, but when we saw each other, it felt very comfortable. We've always had a brother-sister vibe, and we have the same sense of humor. For someone who's such an amazing serious actress, she really is very funny, and I think that humor is so much a part of her work too. 

Dannemora was the first time you adapted a true story for the screen. What's the difference in bringing real people versus fictional characters to life?  And, specifically, how did you build up the characters of Richard Matt, David Sweat, and Joyce "Tilly" Mitchell?

I was very intimidated by the idea of doing a prison story. I know that genre has been done so much, and what I was concerned about was that I'd never been to prison; I don't have that experience in my life. It's something that I, as a person, I think about — not wanting to go to prison. It's just a scary thing to me, and I was afraid of screwing it up. So, my thought was when I first saw the project, "What is the reality? What really happened here?" Like, "Oh my god, this was an old school prison break that happened today?!" So it was all about the details.

There was a report that was done by the Inspector General of New York state, and that became the bible for everything, and we just dug into the reality. Then we had to find the human aspect of it. This woman, this person, was looking for a better life. And, of course, there were the prisoners who don't want to be in prison. So, we looked at these people as human beings who did really bad things in a circumstance that was not a normal circumstance. We dug into the details for fear of getting it wrong. So that meant having technical advisors, getting to visit the real prison, getting to visit David Sweat and talking to him was really important. And then working with amazing actors who instinctually know that they have to find that reality. Because that's something where you can cast an actor and they have to really embody it and take it on, and when you're working with actors who really take that seriously, that's a lot of the job.


From left to right: Benicio del Toro and Ben Stiller on the set of 'Escape at Dannemora'


The very last images you leave viewers with in Dannemora are stills of Richard Matt's art. Despite being a convicted murderer, he was quite a talented painter. What was the intent behind ending the series with his art? 

At the end of the day, I didn't want to make any judgments. I felt like you can show these characters as they really were as much as possible and then let the audience grapple with that. Because I feel like that's what we do as people when we read about these stories, you just wonder how could a person do something like this, like what does this mean and who are they? I wasn't in any way trying to say that we should feel bad for this person because he was a murderer, but he was a human being. And he did create art. To me, that someone could have this aspect to who they were and also do the things they did was sort of fascinating. So, I thought, "OK at the end of this maybe for the audience to just have something else to think about." Like, "OK, he self-destructed, he was a murderer, kind of a scary guy, a murderer, but also an artist." I find it in some way makes me think about what it means to be a person. 

Starting to kind of shift a bit into chatting about Severance now — there are undeniable parallels between Dannemora and… 

Can I tell you something? It's kind of obvious looking at it now, but I wasn't thinking about that! I swear! When I was doing Severance, first off, I loved what [creator] Dan [Erickson] had written, and he wrote the pilot like five years ago, and we were trying to get it made for a long time. We knew what the season was going to be as we developed it, but I swear that it was a year into making Severance where I was like, "Oh, wait a minute! This is like a prison escape!"

Oh, wow! So how much would you say your experience with the prison setting at Dannemora inform how you built out the shady corporate world of Lumon in Severance

I was thinking that I was doing something so different than Dannemora! And aesthetically I was, and in terms of what I was drawn to consciously was not the prison aspect. But one day I suddenly realized the similarities. The Lumon set was a little crazy. There were exits to the hallways, but then we would put walls up sometimes so you couldn't get out so we could do a certain shot. And then one day I was walking the hallways and I was like, "Oh my god, this is reminding me of the prison set we had." So, I guess that it was something that was subconscious in there. The idea that humans are going to be humans no matter what circumstances you put them in, and you see that in Severance — that human beings are still going to be human even if you sever them from their memories. What comes through? What doesn't? And if you try to control them, how do they react?

Theodore Shapiro's score for Severance sets the stage for everything that's going on within the show and really gives the narrative an emotional touchstone and heartbeat. How was the score shaped over the course of the series? 

With Severance we had a very long period where we were trying to get the show made, then casting and prep was six, seven, eight months before the pandemic even happened. He wrote the music early on, and that really influenced everything. When we figured out what the theme would be, I'd play it on the set sometimes, and I think that really affected the making of the show. 


Ben Stiller on the set of 'Severance'

Courtesy of ID PR

Behind the scenes of 'Severance'

Courtesy of ID PR

This show is so unique for so many reasons, but one of which is that many of the characters are playing "innie" versions of themselves, and innies are childlike versions of adults. What sorts of conversations did you have with the actors playing "severed" characters about how to play the innies, specifically in the episode where they're all in the unfamiliar real world? Was there a sort of "Innie Bible"?

There wasn't a bible, but there were discussions. Every actor is different, and when you hire actors who are really good, they do so much of that work because all they're thinking about is their character and reading everything through the lens of their character. So, they knew that there were going to be all these things that they had never experienced. Like when Mark goes outside to talk to Ricken, he's never been outside before! And Adam [Scott] and I had a moment where he was like, "Hey, I've never been outside," but then it was like, how much can we really get into that because we're also trying to tell the story in the moment. So, if he had a moment of feeling the air or something it might be too much because, really, the scene is that he's going to talk to Ricken. 

There are a lot of those moments where there are questions. Not as much with John [Turturro] because I think John does so much of his work internally. There was the question of 'how much seeps through?' And we had to assume that, somewhere in him, Irving knows how to drive a car. 

The last three episodes — particularly the final two — are masterworks of suspense. How did you work on building up the tension to the fever pitch of the finale? 

[Director] Aoife [McArdle] and I were directing the episodes, and we were shooting them in block shooting, which means that over the course of the shoot we didn't shoot every episode in order. This was out of necessity for the sets and winter and because our production kept getting delayed because of COVID, but I knew that Episode 9 had to be different than all the other episodes because of the experience they were having. So Jessica Lee Gagné and I — we worked on Dannemora together — we thought about it like Episode 5 in Dannemora, which is counting down the last day before they escape, and we said it had to have that feel to it. That episode of Dannemorais all connected with wall-to-wall score in it also. I love the show 24, and so we also had a little bit of a 24 homage in there. There's a "tick tick" sound in the background, and the screen splits for the first image. And, like with 24, I thought this had to be real-time connected. 

The camera in most of the show is very static or like these very composed images, and there was no Steadicam used in the series. Well, we used it one day for the Music Dance Experience for Milchick, but otherwise, we always used dollies to make it all very steady. So, for Episode 9, we said let's do it all Steadicam; let's make this completely flowing and feel different. Because the innies, it's like a drug trip for them, so everything should be flowing and moving all the time. 

Then we were just trying to figure out how to do the POV versus not POV for the innies. You know that Gaspar Noé movie, Enter the Void? It's a wild movie. Incredible POV stuff. It's all POV, but we couldn't do it because we had to show stuff. So, we decided on this shifting off of POVs where sometimes we'd be in Mark's POV, and then we'd pan around and he's in the shot. We had to figure out how to cheat it so you could see him and also get into his POV. Hopefully the story is leading you to this point, but honestly, we didn't know how it would work until we saw it all together. The thing I learned about the show, since I had never been involved with an open-ended series and how people engage with it, is that at the end of the day, people are so invested in the characters. I think at that point, by Episode 9, you're invested in these people and the things that they're discovering, and that's what it's all about. So, it was just intuitively trying to stay with that and the characters. 

Given where we end up with all four of our innies, it seems unlikely that they'll return to that gorgeously realized Lumon labyrinth, which would be such a shame. Is there anything you can tell me about Season 2? 

After I do this interview, I am literally going to sit with Dan and our other showrunner and talk about it. I do not want to say anything about Season 2 other than that everything that happened has to be somehow dealt with. The thing I'm very aware of is that I don't want this to be a show where people are always saying, "Oh, gosh, you never know what's going on and there's never answers to any questions." I feel like we owe it to an audience to give them enough so that they can hang on to something. That's all I'll say! It's looking really good for Season 2!