Ben Stiller uncovers his serious side with ‘Escape at Dannemora,’ Showtime’s latest auteur TV series

Nov. 15, 2018 3 AM PT

Reporting from Brooklyn — Brick walls coated in grime. Rows of industrial sewing machines. Fluorescent lights. The room isn’t much to look at. But Ben Stiller is still excited about it.

On this gray morning in December Stiller proudly shows visitors around the set of “Escape at Dannemora,” the seven-episode limited series he’s directing. Deep in Brooklyn, the dank, old industrial space is a stand-in for Tailor Shop 9 at the Clinton Correctional Facility in upstate New York, the maximum security prison that in 2015 became the site of perhaps the most notorious breakout in modern memory.

With an almost forensic level of detail, Stiller sketches a map of the 19th century penitentiary on the back of a script page, explaining where the shop was located in relation to the mess hall, the cellblock and the steam pipe through which convicted murderers Richard Matt and David Sweat escaped, triggering a three-week manhunt and round-the-clock news coverage.

In the series, which premieres Sunday on Showtime, Benicio Del Toro and Paul Dano star respectively as Matt and Sweat. The inmates plotted their breakout for six months with assistance from the civilian supervisor of the tailor shop, Joyce “Tilly” Mitchell (Patricia Arquette), who is believed to have had sexual relationships with both men. Using hacksaws she smuggled to them via blocks of frozen ground beef, Sweat and Matt cut holes in the walls of their cells, tunneled through the bowels of the prison and climbed to freedom out of a manhole — a spectacular feat that immediately invited comparisons to “The Shawshank Redemption.”

But if the escape seemed like something straight out of the Hollywood imagination, Stiller is determined to ground this stranger-than-fiction tale with nitty-gritty details, bringing to life the prison sometimes called “Little Siberia” and the sordid human drama that unfolded within its walls with painstaking verisimilitude.

A multihyphenate primarily associated with comedy, Stiller is the first to concede he’s not the obvious choice for the material. His work as a director began 25 years ago with the Gen-X touchstone “Reality Bites” and continued with “Zoolander,” “The Secret Life of Walter Mitty” and “Tropic Thunder.”

“Escape at Dannemora” represents a number of firsts for him as a director: his first drama, his first fact-based project, his first TV gig since the failed Fox pilot (and cult favorite) “Heat Vision and Jack” in 1999. And, oh yeah, the first time he’s directed something with a 400-page script and a running time of 7.5 hours.

The real deal

This particular morning, Stiller has been filming take after take of a tense scene between Arquette, whose character, distracted by the escape plot, is struggling to fulfill an order for inmate clothing, and Del Toro, who tries to calm her frayed nerves. Standing in front of the raised platform where she sits, Del Toro as Matt tells her he has “aquafina” — prison moonshine — and lures her to the backroom for a sexual encounter. The other inmates look up from their piecework and roll their eyes at the brazenness of it all.

“The story was always interesting for me on a human level,” Stiller says afterward. “Prisons are created by people, but people are always going to be people and have human desires and wants.”

Though Stiller didn’t follow the escape closely at the time it was happening — he was in Italy filming “Zoolander 2” — “Dannemora” co-creators Michael Tolkin and Brett Johnson, like millions of Americans, were captivated by the 2015 breakout. The writers, who were then working on the Showtime crime drama “Ray Donovan,” began to map out a series version of the story while Sweat and Matt were still on the loose. Early in the development process, Stiller was approached about directing.

“We knew we couldn’t have somebody who lacked a sense of humor,” explains Johnson, speaking by phone with Tolkin. “It’s not a comedy, but there’s a lot of stuff that’s organically funny, ironic.”

Stiller wasn’t specifically looking to do television, but he was eager to try something more overtly dramatic. So he asked Tolkin and Johnson to annotate the two scripts they’d written, marking what was fact drawn from information available at the time and what was creative license. It was about an even split, say the writers.

After months of conversation, Stiller decided to pass “reluctantly, painfully.”

“I was very, very, interested in the facts. It was the only way I could find a way into it, because it’s just so outside of anything I’d really done before,” Stiller says in a later interview, nearly a year after the day on location in Brooklyn, as he’s winding down post-production on the series. “Because it was so sensational, and so much like a movie, I really was interested in what the reality of how something like this happens in this day and age.”

Then in June 2016, the New York state inspector general released a 150-page report outlining the “chronic complacency” and elaborate efforts that enabled the escape. “Every detail you would want was in that report,” Johnson says. “Here was a story maybe as good as any novel published in the year 2015 that was sitting there on the ny.gov website for free.”

(Others have already attempted to tell the story: “New York Prison Break: The Seduction of Joyce Mitchell,” a Lifetime movie starring Penelope Ann Miller, came out last year.)

Cinematic TV

With the report now providing an abundance of facts, Stiller was ready to commit. The writers pored over hundreds of pages of interviews conducted as part of the investigation to flesh out the backstories of the main characters, including the vicious murders committed by Matt and Sweat and Mitchell’s rocky marriage to another prison employee.

Stiller weighed in on the scripts with meticulous notes. “In terms of work ethic, I’ve never seen anything even close to Ben,” says Johnson.

“Escape at Dannemora,” Stiller says, represents “the kind of subject matter that isn’t really being made by the studios anymore.”

“Now being on the other side of it,” Johnson says, “we both feel there’s no one else who could have done it.”

Johnson also points out that Stiller’s films “are incredibly cinematic. They’re not two guys sitting in a room doing fart jokes. ‘Tropic Thunder’ cinematically is as accomplished as most Vietnam war films.”

The writers also praise the director’s instinct for casting and his ability to attract big-name talent, including two Oscar winners, Arquette and Del Toro.

Arquette, whose transformation into Mitchell involved 40 extra pounds, prosthetic teeth, dark contact lenses and a thick, almost Midwestern accent, was the first of the key cast to come on board.

She had known Stiller since they worked together on the antic David O. Russell comedy “Flirting With Disaster.” Though she wasn’t surprised by his interest in darker material, she was struck by his vision for the story.

“Acting was the priority, but he really knew the shots he wanted, the lenses he wanted, where he wanted the camera,” she says. “He was, like, obsessed with this project.”

Stiller was assiduous about using real people and places whenever possible. Former inmates were hired as consultants and background players. Episodes were filmed on location at the grocery store where Mitchell bought her doughnuts, in the field near the Canadian border where Sweat was shot and captured, and even in the ramshackle trailer where Matt spent the night before he was killed — though, as Johnson notes, it was rotated 180 degrees to better capture the light.

“So my joke with Ben was that’s why our show is complete bull… . There were times when I thought: Why do we need to shoot this in the real spot? It’s a field with trees.”

Perhaps more understandable was Stiller’s insistence on filming in Dannemora, and he faced skepticism from locals who wondered why “Zoolander’s” “Blue Steel” guy was making a movie about their suddenly infamous town.

“I think they were a little cautious. That might be a kind word,” he says with a laugh. “I really understood why they felt skeptical. They heard it was me directing so they might have assumed it was going to be a comedy: ‘Oh, they’re going to make fun of us.’ ”

Stiller was instrumental in winning over wary officials, Tolkin says. “Ben went out of his way to make himself available to the community. There isn’t a mantelpiece in the county that doesn’t have a selfie with Ben. He really convinced them he wasn’t going to make them the butt of the joke.”

The production was ultimately granted permission to film scenes in the north yard of the prison and surrounding streets, including the manhole from which Sweat and Matt emerged. And while they were permitted to tour inside the facility, they could not take any pictures. So production designer Mark Ricker sketched the cellblock and recreated it, in all its claustrophobic glory, at a Queens studio.

Stiller was even able to meet with Sweat, who was originally imprisoned for murdering a police officer in 2002 and is now in solitary confinement. Over a five-hour meeting, Sweat provided further details about the breakout and his time on the run with Matt.

“He was pretty candid,” Stiller says, noting one major exception: “There were certain things he wouldn’t talk about, or we feel he wasn’t telling the truth about, in terms of his relationship with Joyce Mitchell.”

Both Sweat and Mitchell have denied their relationship was sexual, although they exchanged intimate letters and were often seen going into the backroom of the tailor shop together. Their scenes together in “Escape at Dannemora” are one of the areas where the creators have taken some necessary liberties.

Other times reality was deemed a little heavy-handed: Stiller ultimately cut a scene in which Sweat and Matt wondered how long it took Tim Robbins’ character to escape in “The Shawshank Redemption” because it felt “too meta,” Stiller says, even though it was based on Sweat’s account.

Stiller’s commitment to detail lends “Escape at Dannemora” a palpable sense of place. The series captures the austerity and isolation of Dannemora, the kind of rural, working-class community that has historically been overlooked by Hollywood — and, to some extent, Washington. Donald Trump announced his candidacy for presidency during the breakout, a fact that’s deftly woven into the backdrop of the story.

Stiller’s dedication also extended to his willingness to break with the usual practice in series television and direct every episode of “Dannemora” — joining the rarified list of film directors (Steven Soderbergh, David Lynch, Spike Lee) who’ve helmed entire seasons of television — a feat of endurance not unlike cutting through the walls of a prison with a hacksaw. Stiller’s been actively working on the project for more than two years, four times longer than it took Sweat and Matt to carry off their escape.

While the gritty subject matter made him “very, very grateful to be able to leave at the end of the day,” he says, “the amount of work that we had to get through in a certain amount of time was probably the most oppressive part of it.”

It helped that he wasn’t acting in the series. “I found it really freeing to be able to finally do all the things as a director you want to do, that you can’t do when you’re acting, which is basically be in two places at one time.”

For Del Toro, having a single director alleviated his anxiety about crafting a coherent performance in a long-form series that, out of necessity, filmed out of order with scenes from multiple episodes sometimes shooting in a single day.

“Ben really had the whole show in his head. Not only did he have an idea of the arc of the characters emotionally but also about the journey of the seven episodes, how they all had a different feeling, but collectively told one story. That really helped every department. It was essential for it to be what it is,” he says.

Stiller looks forward to viewers recreating his own journey through the story.

“My hope is that people will watch it and go, ‘Oh, that couldn’t happen,’ and then if they do the research, they might see that, ‘Oh, my God, that actually did happen,’ ” he says. “It’s just like a movie — and it is — but it’s also far more interesting than that.”

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