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Escape at Dannemora - Season 1 - Advance Preview

Escape at Dannemora tells the extraordinary and strange true story of the 2015 prison escape from Clinton Correctional Facility in Upstate New York by convicted murderers Richard Matt and David Sweat. A modern day prison escape alone makes for a unique story, but the closer you look at this particular tale, the more confounding and peculiar it becomes. Showtime’s new seven-part series directed by Ben Stiller (of all people!) and written by Brett Johnson and Michael Tolkin takes a very patient approach to the telling of the escape, in particular favouring to delve deep into the months leading up to the event. Stiller’s series is not just fascinated by the process of how one goes about escaping from a prison in 2015, it is also fascinated by the strange and complicated human story – a bizarre love triangle – that made the escape possible in the first place.

This patient approach is sure to test many viewers. Stiller’s name along with the all-star cast he’s assembled here (led by Benicio del Toro, Patricia Arquette, and Paul Dano) is sure to draw people to the premiere tonight on Showtime, but nothing about the series is as flashy as the names attached might suggest. Escape at Dannemora doesn’t romanticize the escape, nor its characters – in fact, it might not even like its characters very much – but because of the way in which it slowly builds and fills out the prison ecosystem and the various personal relationships at the story’s centre, when the last few episodes arrive, they are all the more satisfying, sad, and unsettling.

The escape was very much also an institutional failing, but rarely does the series broaden its scope beyond the walls of the prison and the town beside it where all the prison’s workers live – though Michael Imperioli does cameo as New York Governor Andrew Cuomo. Escape at Dannemora instead sets its sights on the very human stories and failings that allowed for the escape to occur.

At the series’ centre is Tilly Mitchell (a terrific and unrecognisable Arquette) the 51 year-old married woman who worked in the prison’s tailor shop, had affairs with both Matt and Sweat (played equally well by del Toro and Dano), and then was critical in helping them escape. The show spends just as much time with Tilly as it does with the escapees, and its in her where it finds its most mystery and power. Why did she do what she did? What was she thinking? Are we supposed to like her? Empathise with her? Root for her, even? Or should we be horrified, disgusted, condemning? The series presents the character at her most raw, exposed, human. In the end, she’s a contradiction. We understand her deeply, and yet she also remains unreachable.

That unreachable aspect extends to the other two protagonists. While their motives are obvious, the series doesn’t reveal until late in its run why exactly both men were in prison in the first place. Until then, we are just with them, as they go about their lives in confinement, and as they go about preparing to do something so crazy they can hardly believe it. Flickers of humanity shine through at points – the final images of episode 2 are sure to linger with you – but we mostly get a sense of both men through their interactions with one another and with Tilly, though in both cases it’s hard to tell what’s genuine and what’s an act. They have a goal in mind, and are willing to do anything to achieve it. It’s only once they escape that we see both men for who they are. In particular, del Toro’s Matt transforms once outside the prison walls from a calm, intimidating figure to someone almost animalistic.

Until the actual escape, often times Stiller asks us to have fun with Matt and Sweat. We can see that they aren’t the nicest guys in the world (while Matt’s demeanor is calm, there is something indescribably unstable lying just beneath the surface in almost every scene with him in prison), but what they are doing is exciting, and the context of it is so strange, that the series at times chooses to lean into that. Moments of absurd comedy rear their head at points, Stiller acknowledging just how ridiculous this whole thing is. And interspersed through the season are music montages of Sweat and Matt either sawing or hammering their way through a wall or pipe. The fifth episode opens with a wordless, upbeat nine-minute sequence following Sweat made to look like a single take that had me grinning from ear to ear.

When the series ultimately chooses to show us who these three people really are, they aren’t pretty, not flinching at the collateral damage of their past actions. In Sweat, the series seems to see a smart, promising kid who took a wrong turn somewhere, which led to immense tragedy. Someone who could perhaps lead some sort of normal life if he managed to evade capture after the escape. But in Matt and Tilly, the series sees people who are dangerous, deeply flawed, and incapable of living in a normal, functional society.

The question of “Is this all there is?” hangs over each episode like a pall. Everyone from the main trio to more peripheral players (standouts being David Morse as Gene Palmer, a guard who has developed a friendship with Matt over the many years at Clinton, and Eric Lange as Tilly’s husband Lyle) looks around them and sees what could’ve been getting further and further out of reach. Though doomed to fail, our three protagonists try one last time to take their destiny into their own hands, just to fool themselves into thinking that there is more.

Grade: A-

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