Breaking Point

In June 2015, convicted murderers Richard Matt and David Sweat broke out of the Clinton Correctional Facility in Dannemora, New York.

They didn't do it alone. A prison seamstress, Joyce "Tillie" Mitchell, conspired with them. There were lurid reports of sex between Mitchell and both men; the New York Post dubbed her "Shawskank." The daring escape riveted the country, and the ensuing three-week manhunt terrorized the area, which lies near the Canadian border.

Police eventually killed Matt and recaptured Sweat, who returned to jail to serve out a life sentence. Mitchell is serving up to seven years for her part in the escape, which exposed widespread corruption and lapses in security at the antiquated prison.

The breakout is the subject of Escape at Dannemora, a limited series premiering November 18 on Showtime.

Ben Stiller directed all eight episodes from a script by Michael Tolkin and Brett Johnson. Oscar winner Benicio Del Toro plays Matt, Golden Globe nominee Paul Dano is Sweat, and Emmy and Oscar winner Patricia Arquette is Mitchell. Executive-producing are Stiller, Johnson, Tolkin, Michael De Luca, Bryan Zuriff, Nicholas Weinstock and Bill Carraro.

Stiller was filming Zoolander 2 in Italy when he first heard about the story. Tolkin and Johnson, who had met on the Showtime series Ray Donovan, began writing a script even as events were still unfolding. But on his return to the U.S., Stiller wasn't sure there was enough material.

"They had written all they knew was true, but it wasn't a lot," he recalls. "I didn't think I had enough info. What interested me was the reality of how something like this happens."

The full story came together a year later, when the inspector general of New York released 170 pages of transcripts, including lengthy interrogations of Sweat and Mitchell. The documents painted a fascinating picture of how inmates and prison employees alike felt equally imprisoned at Clinton.

One of Hollywood's most bankable comedy stars, Stiller hardly seemed like an obvious choice to direct a prison drama, but the genre has long fascinated him. Even so, he admits, "I was nervous about not getting it right, because it was so outside my experience."

To ensure authenticity, Stiller was meticulous in his attention to detail.

The governor of New York allowed the filmmakers to shoot exteriors around the Clinton prison, including its North Yard. They used a recently decommissioned prison in Pittsburgh for the main within-the-wall exteriors and tunnel sequences. The Clinton manholes that Sweat and Matt escaped through — which had been sealed since the breakout — were reopened for the shoot.

Only the Honor Block — the teeming cellblock area that served as the production's main set — was built on a stage, with an emphasis on its tight quarters and drab surroundings.

"That same color green, the same tiny spaces every day…" Dano recalls. "Our work was there for us — rage, claustrophobia, complicated dynamics." In addition, real-life prison workers and officials who took part in the manhunt appear in the series, and a number of former prisoners serve as extras.

Escape at Dannemora is ultimately about human connection in a bleak, hostile environment that, Dano says, is "the last place you want to show your vulnerability." Richard Matt, nicknamed "Hacksaw" for the brutal murder that landed him behind bars, is the skilled manipulator who seduces Sweat into doing the physical grunt work that makes the escape possible.

"He never met his mom, grew up in orphanages — the only way he could survive was through fear, cruelty and lies," Del Toro says of Matt. "Once I'm acting in front of the camera, it's not my job to judge him. The script lets the audience be the judge."

If Matt is, as Del Toro says, "the CEO of the escape plan," Sweat is his tireless subordinate. A skilled worker in the prison's tailor shop, Sweat masterminds the digging of tunnels and conceives the idea to hacksaw through a steam pipe, through which they eventually shimmy to freedom.

After taking a year off from acting to direct an indie film, Wildlife, Dano welcomed the script's physical demands.

"The idea of working out, crawling through shit, taking a sledgehammer to a wall just felt interesting," he says. Dano also benefited from a sit-down with Sweat at the prison, which left an indelible impression. "It was hard to process," the actor recalls. "Here's this person sitting across from us who's behind bars and who seemed nice and funny and… he's killed somebody."

In prison, Matt and Sweat formed a symbiotic relationship. Matt, an amateur artist, taught Sweat how to draw. But once they were out, the power dynamic shifted.

"Suddenly they're in an environment where Sweat is much more comfortable. He's a survivalist, able to take care of himself out in the woods," Stiller says. "Matt, very much out of his element, slowly started to devolve. The question of whether their friendship was based on mutual need or something else was a question that the actors were exploring all the time."

The most complicated character in the series may be Mitchell, who slept with both men, smuggled tools to them concealed in frozen meat and even briefly plotted with them to kill her husband of 21 years.

For Arquette, the chance to play a middle-aged woman who's unapologetically sexual — a woman who, as she notes, "doesn't have the type of body Hollywood thinks you need to have" — was a revelation.

"Tillie takes care of her needs before anything else," Arquette says. "She doesn't mind being a bitch, and I'm really not a bitch, so I thought it'd be exciting to explore that part of the human experience."

Mitchell's relationship with the killers satisfied different needs. "With Sweat, that's a huge crush; she can imagine what her life would be like with him," Arquette says. "With Matt, he's the only alpha male she's been with. She knows he's a killer and a scary guy, but he's also really exciting. He's much more like her; everything she's capable of doing, he's capable of worse."

Ultimately, she says, "Once you cross a line with a prisoner, they have power over you. It becomes this slippery slope. Tillie's main flaw is wanting to feel alive, to feel love again."

For cast and crew, the eight-month shoot was a grueling and sobering introduction to the harsh realities of incarceration. "The reality of our prison system is, it's really screwed up," Stiller says. "It does not help rehabilitate people."

"My feeling," Del Toro adds, "is that a cage is not something any human being is designed to be in."

Go behind the scenes of emmy's cover shoot with Patricia Arquette, Benicio Del Toro and Paul Dano of Escape at Dannemora. Visit TelevisionAcademy.com/cover.

This article originally appeared in emmy magazine, Issue No. 11, 2018