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How Series Director Newbie Ben Stiller Brought ‘Escape at Dannemora’ to Anxious Cinematic Life

By tackling the series as one long movie, the director applied studio standards and painstaking verisimilitude to an intricate and cinematic true story.

“Escape from Dannemora”


When Ben Stiller agreed to direct all eight hours of the true prison escape saga “Escape at Dannemora” (Showtime), he had no idea what he was in for. The director of six movies (“Zoolander,” “Tropic Thunder,” “The Secret Life of Walter Mitty”) had never helmed a mini-series or series, except for his sketch comedy “The Ben Stiller Show” in the early ’90s; he had directed one pilot (Fox’s “Heat Vision and Jack”). “It was new territory for me,” he said on the phone. “I didn’t know what it would involve.”

When Stiller read the scripts brought to him by showrunners Michael Tolkin and Brett Johnson (“Ray Donovan”), he knew the story had been fictionalized. “I didn’t know enough about what actually happened,” he said. “I read the Inspector General’s 160-page report and decided to start from scratch. They were my partners throughout. We’d block out what the episodes would be, but they’d have to sit down and write. We were trying to set it up. All three of us were in deep together.”

By looking at the series as one long movie, and tackling it one day at a time, Stiller applied studio standards and painstaking verisimilitude to an intricate and cinematic limited series. Critics and awards voters have taken notice, not only to the performances and production values — the show scored 12 Emmy nominations — but Stiller has already collected a directing win from the DGA.

Escape at Dannemora Benicio del Toro

Benicio del Toro in “Escape at Dannemora”

Chris Saunders / Showtime

Stiller managed to commit his three stars before all the scripts were finished. Having worked with Patricia Arquette (“Medium”) on David O. Russell’s “Flirting with Disaster,” Stiller knew she was game for anything. Paul Dano (“War & Peace”) had also shot a series, but Benicio del Toro had never experienced such a lengthy production. And he was used to figuring out his character from the ending backwards.

“He needs to know where the character is headed,” said Stiller. “We knew what [the ending] was and talked to him. He was concerned: Would he be able to sustain a character for seven or eight hours? How would that work? That conversation was new for me too.” He convinced Del Toro with his answer: “I can’t tell you, except that you chip away at it, as a movie, scene by scene, sequence by sequence, and take it as it comes.”

By June 2017, with Del Toro and Paul Dano on board as two inmates who break out of jail with the help of a romantically involved prison worker played by Arquette, Showtime greenlit a seven-hour series.

From the start, Stiller wanted to hew as close to the true story and locations as possible. “I knew we needed to have access to the real prison and shoot up there,” he said. “The prison, and that area, was a character in the story. I knew so little about this world, that I wanted to cling to the facts in order to tell the story as truthfully as possible. What’s interesting about this escape is it actually happened in 2015. How did this old-fashioned prison escape happen in this day and age? As we were finding out the interesting details and story, I felt a lot of fear of not getting it right.”

Escape at Dannemora Paul Dano Benicio del Toro

Paul Dano and Benicio del Toro in “Escape at Dannemora”

Chris Saunders / Showtime

Fear drives Stiller. “You get to this point in your career and there’s a sense of wanting to do things that really excite you and scare you a little,” he said. “You know you can go to a world you’ve been in before, but when something out there is fascinating — ‘Oh, I could really screw this up’ — OK! Something inside me says, ‘I want to see this, and figure out a way.'”

Once production was underway that fall, Stiller and his team didn’t know until the last minute if New York Governor Cuomo would give them access to the Clinton Correctional Facility, in the chilly northwest corner of the state. They had already pored over photographs covering 100 years inside the Dannemora prison, as well as videos shot on the day of the 2015 escape by inmates Richard Matt (Del Toro) and David Sweat (Dano).

“They inspected the prison cell and steam pipes with GoPro video,” said Stiller. “Also the inspectors did trace David Sweat’s route. We didn’t have anything else to go on until we got inside the prison. Once we saw it in real life, it was so big, so stark, a lot cleaner than I thought it would be, almost ’30s Brutalist architecture: cell blocks and cell blocks and lawns and open spaces.”

While they couldn’t shoot inside the prison confines, they were able to examine the inside of the prison — without cameras. Production designer Mark Ricker took a sketch pad on their tour and later duplicated the entire three-story, 60-cell prison block at the Kaufman Astoria Studio soundstage. Invaluably, they were able to shoot a few days on the distinctive exterior north yard, and found a similar prison in Pittsburgh to shoot inside, with tunnels underground.

“Escape at Dannemora”

Christopher Saunders/SHOWTIME

Shooting seven episodes was challenging for the director and his actors, especially series newbie Del Toro. “I’m a sprinter,” he said. “I do movies. Eight weeks. I’m good. I just go under, navigate, do the best I can, finish, forget. Let’s wait for the next job. This one was seven months. And it’s fast; you have to prepare for the unknown. It was like, ‘Whoa, when am I coming up?’ I never saw land for the longest time.”

Sometimes the actors had to jump between different time frames on the same day. “That’s challenging, and I tried not to do it,” said Stiller, who found shooting on the cell block set the most demanding, as it was packed with actor-prisoners who became so acclimated that they were peeing in the non-working toilets and smoking weed. “The atmosphere was the feeling of an actual cell block when you walked in there, a community, it became its own world. Paul and Benicio had to get into their roles, living it every day. To have that energy was pretty exhausting for them.”

The production tried to spread out the days that Dano had to crawl into hot, narrow, dark, tunnels — filmed on a stage, in a Yonkers water treatment plant, and underneath a Pittsburgh prison — not to mention the real manhole in Dannemora. “We tried not to stay down too long,” said Stiller. “A day under a water treatment facility feels like a week. But it was important to give you a real sense of how difficult it was for them to do what they did. Seeing the video the inspectors did of Sweat’s route, it was so tight and claustrophobic, it made me feel uncomfortable, and I wanted to show that to the audience.”

After Sweat determinedly claws his way, night after night, through walls and metal, Stiller’s tour-de-force nine-minute sequence in Episode 5 traces Sweat’s entire escape route: He crawls through a small hole in his cell wall, snakes into a series of narrow steam pipes, and up under a manhole cover on the street outside the prison — and then returns to his cell. Stiller and his team made sure to shoot 17 puzzle pieces throughout the filming, and then stitched them seamlessly together in the editing room.

“I wasn’t looking to innovate,” he said. “I was figuring out ways to do things that felt interesting and yet were integral to the story. I didn’t want to do things to pull you out. It comprised a lot of different pieces and took a lot of planning for the cinematographer and Mark Ricker and visual effects.” When they finished filming that shot they celebrated with a bottle of champagne and a toast to Dano.

Escape at Dannemora Benicio del Toro David Morse

Benicio del Toro and David Morse in “Escape at Dannemora”

Chris Saunders / Showtime

Nobody was going anywhere without help from prison tailor shop seamstress Tilly Mitchell. Arquette had to convince Stiller that she could deglam enough to play the woman who not only has sex with the two cons but supplies them with the tools they need to get out. To play the role, the diminutive Oscar-winner gained 40 pounds. “Patricia had to work on morphing into Tilly and disappear inside the role,” said Stiller. “Patricia had a natural beauty and sexiness about her no matter what; every human being has that aspect. As long as she could disappear within the character physically, that was going to be there inside of her. She was not worrying about being likable in any way.”

Arquette is favored to win the Best Actress Limited Series Emmy: she has already taken home Golden Globe and SAG awards for “Dannemora,” and at the Critics Choice Awards, tied with “Sharp Objects” star Amy Adams. “She gave a performance that was truly scary and to the edge,” said Tolkin.

Escape at Dannemora Paul Dano Benicio del Toro Patricia Arquette

Benicio del Toro and Patricia Arquette in “Escape at Dannemora”

Chris Saunders / Showtime

Episode 6, filmed last after Arquette and Eric Lang (as her husband Lyle Mitchell) lost the 40 pounds of weight they each had gained, flashed back into the past. In the first four episodes, Stiller, Johnson, and Tolkin consciously drew the audience into rooting for inmates Matt and Sweat’s escape from prison.

“We felt there’s a natural inclination to connect to the protagonists, who are not really great people,” said Stiller. “We didn’t want to try to make them likable. We wanted to show them as real people in the environment of the prison. Walking around as prisoners, David Sweat seems like an OK guy, while Richard Matt is manipulative and charming.”

Episode 6 reveals their sordid back stories, how they murdered their way into prison. “In prison dramas we don’t ever see the prisoners’ crimes,” said Stiller. “We know they had histories, but were never aware of it in the present. I thought we had to show what these people had done.”

When budget issues loomed, Showtime tried to talk Stiller into cutting the flashbacks. “That episode was the most important episode,” said Stiller. “If there’s a version of the show that doesn’t have Episode 6, it’s a very different show.”

Escape at Dannemora Paul Dano Benicio del Toro

Paul Dano and Benicio del Toro in “Escape at Dannemora”

Chris Saunders / Showtime

The other fraught editing room decision was just how long viewers could sustain watching Dano’s painstaking journey under the prison. “I felt we had to get into the environment and feel it,” said Stiller. “Hopefully, it was not too much. The reality was written out on the page, I had to make sure we were adhering to it. But now we have to get people to want to watch this. If we show this guy chiseling the wall for three minutes it will drive them crazy and they will stop watching and change the channel. It came to each episode: how to build tension and show something new to focus on, figure out ways to change the approach. We always have a sequence leading to something else. By the end of Episode 4, he’s on the other side of the wall and pops out of the pipe. This is going to be about him getting through the pipe and getting out of the hole.”

He needn’t have worried. “Escape” is a nerve-wracking prison escape adventure that never lets you go.

Final-round Emmy voting is open from Thursday, Aug. 15 through Thursday, Aug. 29 at 10 p.m. PT. Winners for the 71st Primetime Emmys Creative Arts Awards will be announced the weekend of Sept. 14 and 15, with the Primetime Emmys ceremony broadcast live on Fox on Sunday, Sept. 22.

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