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Ben Stiller on 'Escape at Dannemora': A Real-Life Jailbreak Thriller

The comic actor comes of age as a director in a drama starring Patricia Arquette and Benicio Del Toro

Ben Stiller (right) behind the scenes on "Escape at Dannemora."
Benicio Del Toro and Ben Stiller (right) behind the scenes on "Escape at Dannemora."
Christopher Saunders/SHOWTIME

Filmmaker/star Ben Stiller, 52, has grossed $2.8 billion (Zoolander, Tropic Thunder), mostly with comedies that tickle America’s wicked inner child. But his miniseries Escape at Dannemora (Showtime, Nov. 18) proves he can do epic, fact-based drama for grownups, too. It’s about the actual, bizarre 2015 jailbreak at Dannemora, N.Y., by murderers Richard Matt (Benicio Del Toro, 51) and Paul Sweat (Paul Dano, 34), aided by their prison tailor shop boss — and both men’s sex partner — Tilly Mitchell (Patricia Arquette, 50), who plotted but failed to kill her devoted husband Lyle (Eric Lange) and drive their getaway car to Mexico.

Now convict Sweat and Tilly are in prison — her husband still stoutly defends her! — and Stiller has immortalized them in an Emmy-magnet character study that doubles as a gritty, gripping thriller in the style of the ‘70s (Dog Day Afternoon, The Taking of Pelham 123). Stiller tells AARP about the new, seven-hour saga that marks his coming of age as a grownup movie master.

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AARP: The jailbreakers are fascinating characters, more ingenious tunnelers than Steve McQueen in The Great Escape, but Patricia Arquette’s Tilly, the femme fatale who helped them escape, is so weird it’s hard to believe she’s real. And it’s hard to believe that’s Patricia Arquette — it’s a more startling physical transformation of a famous beauty than Charlize Theron in Monster or Nicole Kidman in Destroyer.

Stiller: The story is all true — the more real stuff we discovered, the more crazy it seemed. Tilly wanted to get out of her humdrum, boring life, driving over an hour each way each day to the prison with the prison-worker husband she didn’t seem to be that into, even though he was devoted to her. When she walks into her tailor shop with 50 violent inmates with 13-inch cutting shears, she is the object of attention. It appeals to her ego.

Paul Dano as David Sweat and Patricia Arquette as Tilly in "Escape at Dannemora."
Paul Dano as David Sweat and Patricia Arquette as Tilly in "Escape at Dannemora."
Wilson Webb/Showtime

AARP: So she made love with inmates Sweat and Matt in the back tailor shop room 100 times, and planned a whole new fantasy life with them. Like Etta Place, Butch Cassidy, and the Sundance Kid on the run.

Stiller: There were no video cameras, nobody monitoring what they were doing at all. She was a serial cheater, a very sexual person, who happened to be a 51-year-old grandmother. She was used to manipulating people in her own way.

AARP: The older inmate, Del Toro’s role, was a serious painter — and so is Del Toro, right?

Stiller: Yes, Matt painted, and Benicio draws and paints. I don’t know if Matt could’ve been a professional artist with his own shows, hard to say, but there's something there that was very good. He was obviously a very troubled person, a murderer who eventually self-destructed out on the run. But I think inside of him there was a very sensitive person. In Episode 7 we have a real clip of a guy who knew him saying there’s a real person in there who had sensitivity.  

AARP: He also used his paintings as a scam, a currency to seduce people into doing things for him.

Stiller: Matt and Sweat were trading Matt’s paintings for favors with corrections officers. It had nothing to do necessarily with escaping, but Matt made paintings for one officer’s girlfriend, and in exchange he’d bring him treats from the outside.

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AARP: Like a package of meat the guard did not know contained a hacksaw blade. Matt skillfully “befriended” the guard. The painting and the con-job relationship were his twin works of art.

Stiller: Matt basically spent his whole life in institutions, and was very used to the way you get things in prison by seducing people in different ways, sexually or in another way.

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AARP: How did he seduce Sweat into helping him escape?

Stiller: Sweat was younger, living in fear because he was a cop killer, a target of corrections officers, so he wanted to get out. But he has very fond memories of hanging out with Matt in prison and on the run, he talks about the time they spent together in a very warm way. So you know that they had a friendship.

AARP: Escape at Dannemora is a great portrait not only of particular people, but of a bleak place, where the rich, urban “summer people” come in for three months, and everyone else lives on the chilly edge of society.

Stiller: When you go to that place, where it’s winter nine months a year, you realize everybody is living in a prison, even the people who work there. Most people work two jobs in a prison-based economy, or they’re waitressing. I think everybody has this desire to escape in some way. It is a tough place to live. And I can understand wanting to have a better life. Like, who doesn't? It’s just where you draw that moral line?

AARP: You were a hit on Broadway and SNL around age 21, then got your own show with Judd Apatow, and then got more famous yet. Are you better at 52 than you were then?

Stiller: I hope we’re all getting better as we go along. Some people are much more fully formed a bit younger; I feel like  for  me, I’ve been constantly trying to find myself as a creative person. Patricia and Benicio and I are all around the same  age-ish,  and came up together, and now they’re very much masters of what they do, very secure, and they could invest and make bold choices.

AARP: You don’t appear onscreen in your jailbreak thriller, just behind the camera. Have you made a jailbreak from being pigeonholed as an actor?

Stiller: Just directing, and not acting, was very freeing for me.