What can the scripts behind Showtime’s Escape at Dannemora teach screenwriters about writing compelling limited series for television and streaming channels?
Escape at Dannemora, the story of an employee at a prison in upstate New York that becomes romantically involved with a pair of inmates and helps them escape.
The seven-part limited series is based on the true story of the 2015 Clinton Correctional Facility escape in upstate New York, which prompted an extensive $22 million manhunt two convicted murderers. They were aided in their escape by a married female prison employee with whom they both became sexually entangled.
The series was created and written by Brett Johnson and Michael Tolkin.
Johnson is a prolific television writer, having written for the likes of Ray Donovan and Mad Men. Tolkin is a long-time Hollywood writer. He wrote the Robert Altman-directed classic The Player, which was based on his novel, and also wrote Hollywood hits like Deep Impact, The Haunting (uncredited), Changing Lanes, and the skateboarding cult classic Gleaming the Cube.
Director Ben Stiller, known more for his comedic acting (There’s Something About Mary, Meet the Parents) and directing (Reality Bites, The Cable Guy, Zoolander, Tropic Thunder), took on the series directing duties with the caveat that they would stick as close to the facts as they possibly could.
The series stars Patricia Arquette (Tilly), Benicio del Toro (Matt), Paul Dano (Sweat), Eric Lange (Lyle), and David Morse (Gene).
Here we take a look at the strengths of the scripts and what screenwriters can learn from the series.
Warning: Spoilers Abound Below
The Appeal of True Crime
The true crime genre has exploded in the last few years, initially regulated to docuseries like Netflix’s Making a Murderer and HBO’s The Jinx. But it was arguably The People v. O. J. Simpson: American Crime Story on FX that triggered the new trend of taking true crime subjects and creating a limited series with a big-name cast.
Audiences are intrigued by true crime stories. We are a curious society, and that curiosity is what makes the true crime genre one of the most in-demand in Hollywood. Production companies, studios, and networks see the appeal, and everyone wants in.
Any true story gives a spec project an edge over others. The real-life aspects of the characters and plot push such projects to another level because of the added intrigue that they offer audiences.
Whether you’re writing a feature film or limited series, having a true story embedded within your work enhances your resume.
And true crime stories offer something a little extra in that respect. So conceptualize and develop your fictional stories for sure, but try to sneak in a compelling true story within your stack of amazing scripts — and if you want an added benefit, look for a true crime story.
And the writers behind Escape at Dannemora had a compelling true crime story indeed. The story of convicted murderers Matt and Sweat, and their accomplice Tilly.
Limited Series or Really Long Movie?
Hollywood stars are more open to television than they ever have been, thanks to the freedom of working on a series that feels like an elongated movie. There’s no long-term commitment to multiple seasons. There’s no danger of being stuck in a role for too long — or worse yet, being typecast.
That’s the appeal of the limited series. The limited series is basically a long movie. Instead of the confines of 110-120 pages for a feature script story, you can push the limits of story and character with upwards of 300 (six-part series) to 500 (ten-part series) pages, give or take.
Escape at Dannemora feels like a movie. The writers don’t take their time developing the characters. Those key character elements are introduced early on in the first episode, whereas a television series with multiple episodes and seasons can create story arcs that last for years.
The limited series is more confined. It’s more cinematic in respect to the ways that concepts, stories, and characters are delivered. And audiences love this limited series trend because there’s no long-term commitment. You can binge a six-part, seven-part, or ten-part limited series over a single weekend and experience the full story without having to wait for another season to be produced.
With the likes of Netflix, HBO, Showtime, Hulu, and Amazon (among many others) spending hundreds of millions of dollars on content — especially limited series — a new platform has been opened for screenwriters.
If you like the cinematic experience of writing features and don’t necessarily want to get into the episodic venture of developing and writing a pilot, multiple episodes, and series bibles laying out a multi-season series arc, the limited series allows you to keep your cinematic roots and play in the hot television market playground as well.
This Isn’t Just Another Shawshank or Escape from Alcatraz
Escape at Dannemora could have been just another prison escape series. All of the elements are there. We have a character or characters cutting through their prison cell walls, hiding such holes, and using dummy bodies. We have the horrible prison life situations. We have characters with a plan of escape.
Director Ben Stiller didn’t want to go that route and give us what we’ve already seen. Even the title was changed from what many initially believed should have been Escape From Dannemora.
Stiller told Slate, “People would probably call it Escape From Dannemora, and at one point we were just going to call it Dannemora, and we landed on ‘Escape at,’ which was the original idea that Brett and Michael Tolkin had, the writers. We didn’t want to do ‘Escape from,’ ‘cause that would’ve been Escape From Alcatraz, maybe. We felt like it just was a little bit different, and also Dannemora is the town where the prison is. It’s also how the prison is known colloquially.”
He went on to elaborate, “It’s Clinton Correctional, right. So we felt like there’s sort of a theme of escape happening. Everybody wants to get out of there. Joyce Mitchell, who Patricia Arquette plays, who works there wants to get out. I think the character that David Morse plays, Gene Palmer, he kind of wants to get out, too. So the idea was sort of: Everybody’s escaping at Dannemora. You know what? I have no actual logical answer for you as to why we did that. We just liked how it sounded.”
To further differentiate it this prison escape tale from Shawshank, Stiller and the writers had the freedom of facts to detail the specific elements of the escape.
In The Shawshank Redemption, we had just a handful of details of how Andy escaped in the end.
But with Escape at Dannemora, Stiller and the writers had a whole investigation report to work from. And that is what offered audiences the most intrigue. Seeing how these characters, in all actuality real people, could escape from a prison in this day and age.
While Escape From Alcatraz is closer in structure to that respect, this limited true crime series had so much more to it — namely the characters and their stories. Alcatraz didn’t offer that deeper look into the characters, primarily because of the limited screen time.
Flawed, but Likable, Characters
If any limited series embraced the notion of presenting characters that are clearly flawed, but still somewhat likable in their own way, Escape at Dannemora is the be all end all.
Tilly is a self-centered grump that treats her husband terribly in so many ways. But there’s empathy there in those first few episodes. She’s written as someone that has apparently had a rough life and dreams of something better. Audiences identify with that. Even if she’s cheating on her husband and treating him like dirt. And despite her constant nagging towards the overly likable Lyle, there are still moments that showcase why their relationship works.
Matt is a convicted murderer (more on that below). He’s using Tilly for his own benefit. He’s the mastermind behind the concept of he and Sweat using her to get what they need to escape. But he’s so charismatic and charming that we, the audience, kind of fall under his spell as well. He’s loyal to Matt. He’s loyal to Gene the guard. And he’s a talented artist to boot. That’s just enough for us to like him.
Sweat is the soft-spoken and equally loyal friend. He’s smart, and we respect that as we watch him do all of the leg work with his skills and wit. But we know he has a dark side as well. We see flashes of violence. He may come off as the peacekeeper in many situations, but we see him as the instigator as well.
These three are no angels, but the writing manages to trick us into liking them and rooting for them. That’s real character development. If we didn’t empathize with these characters, the series would have been a very different viewing experience.
Character empathy is vital to the success of characterization. If you write a character that is too likable, you’re missing out on depth, and such characters don’t feel as real as they could be. Those types of characters will often come off as boring. But when you make us identify with them because they are flawed, just like all of us, then you offer the audience a more cathartic experience. And catharsis is a critical factor to a successful story.
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To keep the audience in suspense, you need to present constant and ever-changing obstacles that the characters must overcome.
For this story, it’s not just about cutting through a wall. There’s no real suspense to that. Thankfully, the real story showcased many different obstacles that Matt and Sweat had to overcome in their escape.
Sure, they cut through their prison cell wall, now what? It’s just a chamber of walkways masked by the dark. They make their way through this labyrinth to find what? Another barrier that they have to break through. But they can’t cut through this wall as they did through their cell walls. They have to break through it.
Okay, so they do that. What now? Do they have to break through yet another wall? Initially, yes. But as a storytelling device, this is repetitive. There has to be something more. Life proved to be more interesting than fiction as Sweat discovered a way to cut through a steam pipe that was turned off for the summer. Now they have to deal with claustrophobia — a whole different kind of obstacle.
So they overcome that and finally make it to a utility hole. Freedom, right? Well, guess what. Tilly isn’t there to pick them up and drive them to Mexico. Here’s another obstacle, but something entirely different.
Now they have to survive the mountains.
While Stiller and the writers had that benefit of real facts that showcased the obstacles the real Matt and Sweat had to go through, this is a lesson in how screenwriters need to craft suspense. The obstacles characters face, whether they be physical or emotional, have to be ever-evolving throughout the story. They can’t be repetitive because your storytelling will become more and more complacent.
It can’t be just another bad guy with a gun, another storm, another relapse, or whatever your concept calls for. Each obstacle — and there has to be many — must take things to the next level and increase the conflict. That’s how great suspense thrillers, action pieces, horror flicks, and even comedic stories prosper.
The defining episode of the limited series is Episode 6.
We’ve spent the first five episodes getting to know the characters as Matt and Sweat embark on their plans to escape from the prison. We watch as Tilly begins to help them. We listen to Matt’s seducing words to Tilly, telling her that she can finally escape her boring marriage with Lyle and her boring job at the prison.
Despite their evident character flaws, we find ourselves drawn into the fantasy of escape. We begin to root for these antiheroes. Until Episode 6.
This is the episode that wisely reminded us who these individuals really were. Stiller likely wanted to honor those lives that have been affected by Matt and Sweat in particular.
Remember, these are convicted murderers. They’re going to spend the rest of their lives in prison. Not because they were wrongfully convicted or made a bad choice in a subjective scenario — as was the case with Andy and Red in The Shawshank Redemption. No, these men murdered someone. A fact that is almost forgotten until Episode 6.
We see their crimes.
Stiller and the writers remind us that we shouldn’t be rooting for these characters. They remind us that this isn’t a fantasy story about a prison escape. It’s a true crime story about two convicted killers.
And that doesn’t stop with Matt and Sweat. It points to Tilly as well. We see that she is a serial cheater that clearly has a lack of morals. She’s self-centered to the extreme. And even wholesome Lyle and his saintly image is flawed. We learn that he and Tilly’s marriage is a result of both of them cheating on their spouses and concocting a false-assault charge against Tilly’s then-husband so that she can get sole custody of her child.
Without Episode 6, this is a near-fantasy prison escape story where we hope Matt and Sweat make it to Canada. And when they fail, it’s tragic.
With Episode 6, this is a true crime series detailing the harrowing escape of convicted murderers and those who knowingly, or unknowingly, helped them. And they get what they deserve in the end.
Kudos to Stiller and the writers for reminding us of the reality, instead of selling us on the fantasy. That’s what makes this limited series work the most.
In the end, Escape at Dannemora can teach you a lot about screenwriting.
It teaches you that true stories, especially true crime, are a hot commodity in the film and television industry — thus you should find a true tale to include within your stacked deck of otherwise fictional scripts.
It teaches you that the limited series is a perfect hybrid of television and film. And an in-demand one at that. So many networks and streaming channels are looking for the next great limited series because they also attract big-name talent.
It teaches you that your projects have to differentiate themselves from similar concepts and themes, much like Escape at Dannemora compared with the otherwise similar Escape from Alcatraz and The Shawshank Redemption.
It teaches you that your characters have to be flawed to be believable and interesting.
It teaches you that you have to constantly throw conflict at your character in the guise of ever-growing and ever-evolving obstacles.
And it teaches you that screenwriters have a responsibility to think their messages through, as far as how you want your stories to be perceived, what themes you want to explore, and how you want your audience to experience your stories and your characters. Escape at Dannemora could have been that prison escape fantasy come to life, but the director and writers wisely reminded us that those escaped convicted murderers weren’t anyone to really root for — this series was about drawing in an audience with true crime facts and enhanced dramatization of such.
So take these lessons and see if they apply to your stories. And if you haven’t seen it yet, watch this brilliant series.
Ken Miyamoto has worked in the film industry for nearly two decades, most notably as a studio liaison for Sony Studios and then as a script reader and story analyst for Sony Pictures.
He has many studio meetings under his belt as a produced screenwriter, meeting with the likes of Sony, Dreamworks, Universal, Disney, Warner Brothers, as well as many production and management companies. He has had a previous development deal with Lionsgate, as well as multiple writing assignments, including the produced miniseries Blackout, starring Anne Heche, Sean Patrick Flanery, Billy Zane, James Brolin, Haylie Duff, Brian Bloom, Eric La Salle, and Bruce Boxleitner. Follow Ken on Twitter @KenMovies