Ben Stiller’s ‘Escape at Dannemora’ Dramatizes One of the Craziest Modern Prison Escapes

Alci Rengifo

The story of the 2015 Clinton Correctional Facility escape is one of those examples of how truth can be stranger than fiction. Showtime’s new limited series “Escape at Dannemora” recounts what took place with fascinating characters, strong performances and a format that can feel much too long. We are living through the era of peak TV when nearly every story is deemed suitable for a full series, but some stories work fine as a shorter affair. But Ben Stiller’s approach as a director still produces a viewable experience that places us inside the very texture of prison life, letting it sink in so we realize why the leads are so desperate to get out.

Inside the Clinton Correctional Facility of Dannemora, New York two lifers toil away, Richard Matt (Benicio Del Toro) and David Sweat (Paul Dano). They work the sowing machines in a prison shop managed by Joyce “Tilly” Tillman (Patricia Arquette). Tillman is stuck in a bland marriage to another prison worker, Lyle (Eric Lange) and likes calling Sweat into the back room for a quickie. Of course the other prisoners, especially Matt, notice. In the prison hierarchy Matt gets privileges because of his time spent inside cultivating a reputation as a smuggler and excellent artist. One of the main guards, Gene Palmer (David Morse) grants him favors and tip offs (Matt reciprocates by painting a beautiful portrait of Palmer’s wife). During a routine cell search, Matt discovers a door leading into a vast tunnel system and realizes there might be a way to hatch an escape. Meanwhile prison authorities catch the rumors of what Tilly is up to in the shop and remove Sweat. She’s heartbroken but Matt sees an opportunity to move in, win her over and use her to aid in his scheme.

What Stiller does so well with this series is create the conditions Matt and Sweat lived in. Like few other shows, we get a very real sense of prison life in all its boredom, empty violence and nearly totalitarian culture of authority. He pays attention to the little details of how prisoners trade objects, smoke out roaches in a cell or barter. Once in a while someone gets annoyed with too much noise and a fist fight can ensue. Into this terrain Stiller places Benicio Del Toro as a slick, darkly charismatic presence. Once again Del Toro proves he’s in the same league as a young Clint Eastwood. All it takes is a stare to get a young punk to know his place. Paul Dano is a bit softer as Sweat but no less conditioned by prison life. When Tilly takes him into the back room we get a sense of his guilty conscience, something Matt has no time for. But the best performance belongs to Patricia Arquette, who completely disappears as Tilly. If you haven’t read the roster when tuning in, it might take a few seconds to realize who we are seeing as a plump, rundown, rural wife living with her own frustrations, stuck to a boring husband. She doesn’t have a single criminal bone in her, but she’s also not the brightest bulb and this combined with loneliness make her a perfect target for Matt. There’s a tragically absurd scene where he seduces her by simply painting her pet dogs. But in another, pathetically funny scene, Lyle drags her to a museum commemorating the War of 1812 and we almost can’t blame her for getting interested in some jailbirds.

The premise features odd but fascinating characters who really did live out these events, so the ingredients are there for an involving narrative. The only true fault in “Escape at Dannemora” is the choice to turn it into a 7-part miniseries. The story simply doesn’t require such a stretch. By episode 4 we are still waiting for the plot to pick up some more steam. Instead Sweat changes cell blocks, Matt eyeballs Tilly in the shop and scenes appear to be stretched out on purpose to give the episode reason for being. Because Tilly herself is trapped in a vortex of boredom, tension simply doesn’t develop. She is interesting to follow, but because we know this all happened we get anxious to see just how she dealt with the jailbreak itself. In a sense the first half of the series is all set up. We get many scenes of Matt and Sweat walking through the same tunnel, tapping walls and breaking rock. At first the details of how they plan their escape are gripping, but after a few episodes we want them to just get on with it. Some of the best prison-break films, like “Midnight Express,” work precisely because they are tight, visceral packages. With this series we feel we get much with the beginning, we can skip the middle and jump back in with the ending.

There are many good things in “Escape at Dannemora,” from its eye for detail to the ending itself, which avoids sensationalism and is more of an inevitable, sad conclusion. These characters are the kind who simply cannot avoid a road towards tragedy. It all comes together because Ben Stiller has been given a stellar cast, who can make the meandering moments feel engaging. Even when it goes on for too long, we’re interested, because this is the kind of story that is so strange it is worth telling in any format.

“Escape at Dannemora” premieres Nov. 18 at 10 p.m. ET on Showtime.