Escape At Dannemora Review: A Smart, Star-Studded Prison Break Drama

Ben Stiller is certainly no stranger to working television. He won an Emmy in 1993 for the short-lived sketch comedy series, The Ben Stiller Show. And he’s certainly no stranger to the director’s chair either, having helmed such films as Reality Bites, The Cable Guy, Zoolander, Tropic Thunder, and more. But Showtime’s new limited series, Escape at Dannemora, is a bit of a departure for the filmmaker. A fictionalized account of the 2015 prison break in New York State, the series takes a sometimes steely, methodical approach to what is otherwise a spectacular and ultimately violent event, and delivers a nuanced seven-episode series that bristles with tension and draws its characters and circumstances with patience and, when necessary, empathy.

The series boasts and impressive cast, with two Academy Award winners, Benicio del Toro and Patricia Arquette, as well as Paul Dano, who, in addition to his acting roles, has seen his directorial debut, Wildlife met with critical acclaim. In other words, Escape at Dannenmora is, thanks to its subject matter as well as its phenomenal cast, what would be classified as an “event” series, something akin to, say, HBO’s Big Little Lies or Sharp Objects, but with a distinctly different kind of built-in audience. Rather than attracting a legion of book readers, Showtime and Stiller aim to capitalize on the newsworthiness of the tawdry story at hand, what with the escape, subsequent manhunt, and highly publicized scandal that detailed the lengths to which civilian employee Tilly Mitchell (Arquette) went in order to assist inmates Richard Matt (Del Toro) and David Sweat (Dano) escape from prison, not to mention the sexual encounters she had with both while working at the Clinton Correctional Facility. The escape itself became a captivating, nearly month-long manhunt for the escapees, and given that it’s likely still fresh in the minds of those who followed the events in the news, well, that’s something of a built-in audience right there.

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Though the real-life story is rife with salacious details, Stiller and the show’s writers’ room (which includes prolific screenwriter Jerry Stahl, whom Stiller portrayed in the 1998 film Permanent Midnight) take their time in getting to the actual prison break. Though the deliberate pace helps build a necessary tension, it’s not as though most viewers don’t already know the outcome of Matt and Sweat’s plan. And if they don’t, it’s not as though the details aren’t a quick internet search away. To compensate for reality’s encroachment on a perfectly good prison break story, Dannemora uses the time at hand to provide the viewer with details of its characters’ lives within the walls of Clinton, filling in the blanks that were perhaps left out of a more straightforward reporting of the facts at hand. In that regard, the narrative stays mostly in the here and now of the story, keeping flashbacks and backstory to minimum (until later in the series), to put its focus on two inmates who successfully manipulated their way to a workable escape plan that was eerily reminiscent of another prison break turned mainstream entertainment, the 1979 Clint Eastwood film, Escape From Alcatraz.

Paul Dano and Benicio Del Toro sitting on a table in Escape at Dannemora Showtime

As successful as Escape at Dannemora is at being a prison break drama, it’s seemingly more interested in being a study of desperate characters and the lengths they’ll go to break free from their overwhelming sense of despair. For Matt and Sweat, a pair of convicts serving life sentences, the desperation is obvious. For Tilly, it’s a little different. Seemingly suffocated in her marriage to Lyle Mitchell, played by a captivating, unrecognizable Eric Lange (The Bridge, Narcos), and stuck in an equally suffocating job at Clinton, Tilly’s circumstances are part of a larger exploration of how people find themselves in prisons of their own making.

With its focus on the dreary workaday existence of people grinding out a living — whether they’re guests of the state or not — just to make ends meet, Dannemora becomes something more than just a plot-driven, point A to point B escape narrative. This also affords Stiller the chance to appreciate details of his characters’ lives, whether they’re behind bars or not. It’s a stifling existence that everyone is eager to flee, including guards like Gene Palmer (David Morse), who takes a liking to Matt and allows him to break the rules from time to time, or Dennis Lambert (Jeremy Bobb, The Knick), who is assigned to Tilly’s group and, as a result, is exposed to the worst-kept secret at the prison: Tilly’s ongoing affair with Sweat.

Escape at Dannemora unfolds at a methodical pace that might be a little less captivating on a week-to-week basis. Though del Toro, Arquette, and Dano are all terrific in their roles, and will likely be awards contenders in 2019, there’s reason to question whether or not audiences will continue tuning in every Sunday night until the end of the year or if they'll wait to watch episodes in chunks. Like Sharp Objects, Dannemora might actually make a better case for its story as a binge-watch. Regardless of how audiences choose to consume this limited series, however, it seems as though Showtime, Stiller, and everyone else involved have a smart, substantive drama on its hands.