Jeffrey Wright Made ‘O.G.’ in a Working Prison to Show the Thin Line Between Us and Them

Jeffrey Wright and director Madeleine Sackler share insights on shooting inside a maximum security prison and how filmmaking can be used to rehabilitate.
OG HBO Movie Jeffrey Wright
Jeffrey Wright in "O.G."

Jeffrey Wright walked out of his cell when the man locked up next door asked him for a favor. Wearing his tan prison onesie, the Emmy-winner and “Westworld” star looked like everyone else inside Indiana’s Pendleton Correctional Facility — an active maximum security prison. Just another guy, in another cell (cell No. 5), serving another sentence. Wright was used to people thinking this. Throughout the shoot, prison guards and the men they’re guarding mistook him for a convict. Most of the time, Wright said they “would literally look directly through me,” but his neighbor on the block was different.

“He said, ‘Hey man, you got any books?'” Wright recalled. “‘I read all my books.'”

So Wright walked back to his cell and picked out some books he thought this guy would appreciate. “[He was an] older tall and lanky white guy, so I got him some Louis L’Amour, I got him ‘Moby Dick,’ and I put the books behind my back and dropped them through his bars. He said, ‘Thank you brother, thank you man,’ and that was it.”

This kind of interaction between actors and inmates — hell, actors and anyone who’s not a member of the cast and crew — is unusual for a Hollywood production, to say the least, but Madeleine Sackler’s drama “O.G.” didn’t stop there. Though plenty of men who are incarcerated (like Wright’s neighbor) didn’t even know the production was going on, others were cast in the film. Still more took filmmaking classes from Sackler and eventually co-directed the documentary, “It’s a Hard Truth Ain’t It,” which was shot at the same time as “O.G.” and premiered on HBO a few days after the feature film.

All of this was done for a few reasons. First, there’s the film — a project Sackler and Wright really believed in — but they also wanted to educate themselves on what it means to be incarcerated in America. Beyond that, they wanted to use filmmaking as a tool for rehabilitation; a concept Sackler started to develop a decade ago.

In 2009, the documentarian first visited a prison. She went with a seven-year-old boy who was going to visit his father, and it was then that Sackler’s perspective shifted. “I saw the impact that just one person’s incarceration has on his family and his community,” she said. “That really set me on this path.”

Her desire to tell the father’s story, as authentically as possible, led her and screenwriter Stephen Belber to conduct interviews at the prison and return to Pendleton to workshop “O.G.” with “many men who are incarcerated there.” Belber wrote and rewrote all the way through the shoot, with notes from Sackler, while the director also started teaching a filmmaking class and even put on a film festival for the men inside.

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Madeleine Sackler directing “O.G.”HBO

From the beginning, Sackler knew she wanted to tell this story “from the inside,” and found the prison’s administration was “really amenable” to her visits, lessons, and ambitions. The state of Indiana cut funding in 2012 for higher education courses in prisons, so as long as the filmmaker was offering free programs, Pendleton was all for them.

Once the script was set, Sackler reached out to every single member of her cast and crew to make sure they were ready to shoot inside the prison.

“I called them directly and answered any questions they had, while emphasizing the fact that this is a challenging environment — and maybe not for the reasons that they’ve pictured from other movies,” Sackler said. “It’s an oppressive space. It’s really difficult, emotionally, to see other human beings in a cage. I can’t emphasize that enough.”

Wright’s eagerness for the project was one reason Sackler waited over a year for his schedule to free up so they could start production. (“Jeffrey was the only person I wanted to play the character of Louis,” she said.) Going into production in the summer of 2016, the actor’s excitement mainly stemmed from what he could learn from the experience, as well as what he could give back.

“[But] on a more basic level, maybe a selfish level, I was curious if I could pull it off,” Wright said. “I think it’s pretty presumptuous to walk into a prison and convince a bunch of incarcerated men that you’re one of them.”

Of course, that’s exactly what he had to do. Louis has been incarcerated for 24 years. He’s about to be released on parole, and “O.G.” deals with his desire to be free while simultaneously being afraid of leaving. After so much time behind bars and the fresh temptation of escaping them, Wright said he “fed off the energy” inside the prison to channel Louis’ “emotional rawness” and unique intensity.

“They’re on a different level of emotional bedrock,” he said. “It wasn’t like anything that I had experienced or any crew that I had been around before.”

Wright wanted it to be clear the film and documentary, along with the outreach done to listen to the men’s stories, isn’t about building up sympathy for the violent criminals inside.  “All of this is not to kind of feel sorry for these guys,” he said, but there was a “sense of trauma” inside the prison he couldn’t shake.

“I think the film was very much about the debilitation of the psyche and the social abilities that come along with long-term punishment,” he said. “So the question is around the balance between punishment and reform because these guys are being shaped for anything but integration into society — those skills are atrophying. The ability to command choice is atrophying, and what’s being honed on the inside is the ability to solve problems through physicality.”

OG HBO Movie Jeffrey Wright Theotus Carter behind the scenes
Jeffrey Wright and Theothus Carter making “O.G.”HBO

But even more than how our criminal justice system encourages “more criminality and more violence” instead of actively rehabilitating the people who are incarcerated, Wright said this kind of work isn’t about the men and women currently behind bars.

“I look at it not so much as being about them, as it being about those who are behind them — who are on a pathway toward being them, toward incarceration, and what we can do as society to redirect them toward being more productive citizens,” Wright said.

For her part, Sackler said she first saw how filmmaking could be used for rehabilitation on accident. During her workshops at Pendleton, she came up with an exercise where the men would partner up and interview each other, then they would share their partner’s story with the group — essentially replicating the experience of a documentarian. Sackler wanted them to understand “the power in the way you ask questions,” as well as how telling a story with those answers can be meaningful.

“I could see the men becoming documentary filmmakers because they were both deeply concerned about the truth — like, you could feel it in how they told the stories, that they really wanted to do right by their partner,” she said. “They really wanted the audience, the rest of the room, to feel what they felt about it. Whether it was funny or heartbreaking, they wanted us to get what they got out of it. To me, that’s filmmaking. So we just expanded from that.”

Sackler said “O.G.” and “It’s a Hard Truth Ain’t It” simply “expanded from that” idea. Both features premiered at the Tribeca Film Festival — where some of the co-directors Skyped in from the prison to take audience questions — and now each film is available on HBO.

The reception to each project will be telling. Wright said he thinks “there’s a segment of the population that gets off on the incarceration and degradation of certain people in certain communities,” but he believes more people want a better society through reform.

“I certainly hope that it’s viewed by lawmakers,” he said. “I hope at the very least they ask themselves, how did we pull that off? How were we able to do that? How were we able to go in and do something constructive and positive beyond the story itself? How were we able to go in and do something constructive with men who are viewed as the dregs of society and whom society has turned its back on?”

But even after all of these conversations, self-reflections, and experiences, the simple act of borrowing a book helped answer a larger question for Wright. It all came down to what he called “the power of clothing.”

“That piece of clothing is like a piece of magic cloth,” he said. “It kind of revealed to me that I, and most of us, are not very different than those men. Just putting on that onesie can make you one of them, and it was only because of the opportunities that I have had in my life — opportunities provided by my family, opportunities provided by education, and educational institutions, opportunities provided by mentors — that differentiate me from those guys. […] So while it was a challenging role to pull off authentically, I realized that the space between me and many of those men inside there was really as thin as that prison uniform.”

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