Why Prison Drama Escape at Dannemora Is the Perfect Step for Director Ben Stiller

It turns out that spending more than three decades making pastiches and parodies translates into plenty of skill once it comes time to go straight. That’s what Escape at Dannemora, Ben Stiller’s dramatic TV directing debut, proves for the longtime comedy multi-hyphenate, who made his bones razzing Martin Scorsese and LL Cool J.

Stiller, who directed all seven episodes of Showtime’s limited series (in addition to serving as executive producer), has certainly developed pet themes over the course of his directing career, in his comedies (The Ben Stiller Show, Zoolander, Tropic Thunder) and off-comedies (Reality Bites, The Cable Guy, The Secret Life of Walter Mitty) alike, and Escape at Dannemora pays homage to his favorites. With a premise that has the same realistic absurdity as Dog Day Afternoon, Dannemora’s love-triangle-turned-prison-escape has plenty of unfulfilled daydreamers running amok within its genre thrills—a perfect place for Stiller to flex his chops using characters well in his comfort zone.

Inmates Richard Matt (Benicio del Toro) and David Sweat (Paul Dano) were both murderers on the Honor Block of Clinton Correctional Facility back in 2015. Joyce “Tilly” Mitchell (Patricia Arquette) was a prison employee in charge of the sewing shop who became involved with both men, eventually helping them escape. If you didn’t know it was true, it’d sound crazy. If you didn’t know it was true, Stiller’s grounded portrait of Dannemora, N.Y. and its surrounding areas—and the hokey, where-are-they-now end credits that should’ve died out long before “Today, we call them computers” became a meme—make it obvious.

Filming on location immediately sets the tone. Even when shooting the crunched Nightmare on Elm Street of metal girders, bars, fences, pipes, and benches of an frigid prison (taking plenty of his framing from cramped and confined movies like One Flew Over the Cuckoo’s Nest and Escape from Alcatraz), Stiller wonders in big, steady establishing shots, bereft of any colors but greys and blues. Parking lots, prison complexes, a town with the promise of mountains on the horizon: Stiller is staggered that this small collision of three assholes can make any amount of noise in the grand scheme of things. He tackled a similar visual theme in his 2013 film The Secret Life of Walter Mitty, with a typically infinitesimal actor juxtaposed against intense Icelandic beauty. Here, the beauty is smaller in scale because the ambitions are lower, reduced by the expectation-tempering realities of prison life.

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Establishing routine and boredom—waking up next to your slobby husband, coming to work, banging a con, and watching NCIS back at home—works just as well outside as in. Like Better Call Saul’s masterclass in mundanity, Dannemora erects a barrier between the prisoners that want freedom and the civilians who squander it. Cramming prison workers into a salon, a Chili’s, or a darkened museum theater in their downtime is as insulting to the prisoners as it is depressing for the employees. Stiller loves to stifle, especially when that restrained emotion finally breaks free.

The end of the first episode features a shot / reverse shot sequence of Tilly and a dapper man who looks startlingly like del Toro getting into his car with two younger women from a bar. The back and forth, which slurs into dreams with slo-mo, is tight on Tilly’s face and hair while taking in all of the man (his car, his clothing, his posture) until he acknowledges her stare and doffs his cap. That moment gets a tighter shot, playing into Tilly’s fantasy—the escapist wont that’s led to her affair with Sweat—and causing her to smile at its potential. Yeah, she’s a babe. A romantic, desirable babe. She could be picked up by a handsome stranger. Then the car door shuts and she’s thrust back to reality. A cold reality, where she’s married to someone who took her to a War of 1812 documentary and convicts are using her to escape. Indeed, the escape itself is mind-numbing as well. Hacking and sawing and hammering away at metal, brick, and concrete is a job of inches: every night, feeling the vibrations run up the sledgehammer into your arm, making no visible progress. When Stiller gets his own Shawshank moment, it caps an energetic tracking shot with a bittersweet digestif that bottles the whole thing into a beautifully restrained sequence.

This constant dissatisfaction, prevalent in sex scenes and the obstinate social and economic immobility paralyzing the prison’s staff in the outside world, takes from the unsympathetic, mildly amused, slightly cruel detachment of I, Tonya or Gone Girl. Hope is rare. But inside? Unstoppable desire crashes over and over again into the grit of Stiller’s influences, the combination of which climaxes in a terrifying piece of claustrophobia, combining the physical constraints of Buried and the daily drudgery of Michelangelo’s Sistine Chapel.

“I want to be part of your dream,” Sweat tells Matt when sealing their freedom-bound collaboration. The complexity and scale of the prison counteract the more simplistic imagery (so many birds flying, horses running free) that underlines this dream, juxtaposing the reality of escape with the fantasy of it. Zooming out for—or in from—insanely long shots that make us do the tracking while we try to sift through the rest of the prison’s astounding clutter Dannemora’s aesthetic is deeply retro, almost like The Deuce—though David Simon’s HBO drama is set in the 1970s, and not just reminiscent of it. Stiller even uses a freeze-frame title card once. It rules.

Mostly, though, his direction of Dannemora is not too ostentatiously “stylish.” His camera doesn’t often make fancy moves unless it’s one of a few impressive long takes following a specific inmate or conversation. Stiller’s finest skill here is knowing when to hold on his killer cast. Studio comedies don’t move the camera much either, after all, and Stiller knows when to let the crowd-pleasers do their job.

Whether it’s a striking overhead shot of prisoners moving about or a static gaze at a lonesome Sprite, Stiller and cinematographer Jessica Lee Gagné (who shot the gorgeous neo-noir Sweet Virginia) work out solidly blocked, elegant frames that set a deliberate pace only interrupted by the endless milking of its hour-and-a-half finale. But what can you expect from someone celebrating their first major dramatic project, especially one that covers so many different geographies, emotions, and styles?

There are a few flourishes of personality, too. Slamming pop music up against the prison system (in a way distinct from Scorsese’s see-the-lyrics style) feels slightly weird—almost anachronistic—until you realize it’s just hitting you how surreal it is that penal labor and Ariana Grande exist concurrently. The vindictive visual symmetry of the story belies an intriguingly cynical edge, in particular for a director who’s primarily been sympathetic to his doomed and spacey soul-searchers. Also, I’m almost completely sure there’s a very brief homage to the shot of Zoolander walking with a pickaxe in the mine. Sprinkling bits and pieces of his evolving visual style in with plenty of inspiration from the greats—it’s no mistake The Cable Guy took from Cape Fear—Stiller delivers Escape at Dannemora with his vision intact and daydreams fulfilled.

Escape at Dannemora airs Sundays at 10 p.m. on Showtime.

Jacob Oller is a writer and film critic whose writing has appeared in The Guardian, Playboy, Roger Ebert, Film School Rejects, Chicagoist, Vague Visages, and other publications. He lives in Chicago, plays Dungeons and Dragons, and struggles not to kill his two cats daily. You can follow him on Twitter here: @jacoboller.