A version of this story about Ben Stiller first appeared in the Down to the Wire issue of TheWrap’s Emmy magazine.
Over the years, we’ve seen that Ben Stiller always acts in things he directs, and almost always sticks to comedy. But the limited series “Escape at Dannemora” changed that, winning Stiller an Emmy nomination and a Directors Guild Award in the process.
The seven-part, seven-and-a-half hour true-life saga about Joyce “Tilly” Mitchell (Patricia Arquette), a prison worker who helped two convicted murderers escape from a New York facility in 2015 is the longest thing he’s ever directed, by far the most serious and the only one in which Stiller himself never makes an appearance in front of the camera.
“I have to say, over the years I’ve always wanted to do that,” he said of the decision to only direct the miniseries about a real-life prison break, starring Benicio del Toro and Paul Dano as inmates and Patricia Arquette as the prison employee who helps them escape.
“Even a bunch of the movies that I ended up acting and directing together, originally I wasn’t going to do both. Going back to ‘Zoolander,’ I remember trying to find somebody else to direct it. On ‘Tropic Thunder,’ I didn’t want to be in it originally. It’s really, really hard to do both jobs well — and from the first day of shooting, it was really freeing to know that I didn’t have to be a part of it. I remember thinking, ‘This feels totally different.'”
It was also totally different because Stiller had never done a long-form project that told a continuous story, or one that shot for nearly as long as this seven-month production did. “I had no idea how to approach it, to tell you the truth,” he said. “I knew that we had to shoot it the same way we did a movie, because of the locations.
“But in terms of the amount to be shot, there was so much that it became about having to let go of certain things I’d done in the past, preparation-wise. It was too much to think about how you’re going to shoot a scene four months from now.
“I usually would storyboard almost everything, and on this thing I really only storyboarded one sequence.” (It was a nine-minute scene in which Paul Dano, playing one of the two prisoners who escape, tests the prison escape route, which was actually shot in 17 different pieces at four different locations.) “I had to let go, get in the room with the actors and our cinematographer and figure out what the scene was, and then figure out how to shoot it on the day.”
The sheer length of the shoot, he added, did eventually get to people. “It was hard for everybody when we got to Day 90 and Day 100 and Day 110,” he said. “You start to want to just have a normal life, because it takes over everything. But as a group we felt that we were chipping away at it every day.”
Stiller and creators Brett Johnson and Michael Tolkin went into the project knowing that the real-life Mitchell would likely not approve of their dramatization — and she didn’t, at one point calling Stiller a “son-of-a-bitch liar.”
“From my point of view, I tried to tell it as accurately as we could based on the research we did,” he said. “There is nothing in there that’s not based either on specific research or facts that indicate something happened. It’s based on what we do know. Of course she’s going to have her point of view on it, but she was never really telling the truth all along, so it’s hard to know what’s true and what’s not true in what she said.
“That being said, it’s not a documentary.”
And does the success of “Dannemora” mean that we’re liable to see Stiller doing more work as only a director, and doing more straight drama than in the past?
“Yeah, sure,” he said. “I found it really enjoyable doing this. Comedy is really hard because there is a very specific metric on it, which is the audience is laughing or they’re not laughing. On this, it’s really fun to have different criteria for what you’re doing.
“I think in lot of ways comedy is as challenging as anything, but to have the freedom to do drama and to not cast myself opens things up a lot more. I hope I get to do more projects like this.”
Read more of the Down to the Wire issue of TheWrap’s Emmy magazine.