R.J. Cutler: Still 'Bullish' on Docs, Bring the 'Bank Robber Mentality'
By Richard Rushfield
June 11, 2025
All week, I've been having conversations with some of the smartest people I know in this industry to talk about the state of the business, including Lorenzo DiBonaventura and Colin Callender. These are people who have accomplished big things in their time and continue doing so, and who have, notably, built careers with longevity, and more importantly, have the ability to share their thoughts uncensored today.
My third maven is the Emmy Award-winning documentary filmmaker R.J. Cutler. Born in Great Neck, New York, Cutler began his career in the theater and on public radio before coming to documentary film. He started his doc journey alongside legendary documentarians D.A. Pennebaker and Chris Hegedus, producing the pair’s seminal 1993 political doc The War Room. In the years since, Cutler has won acclaim for his frequent, no-holds-barred portraits of culture figures, including Anna Wintour (The September Issue), Vice President Dick Cheney (The World According to Dick Cheney), Billie Eilish (Billie Eilish: The World’s a Little Blurry), Elton John (Elton John: Never Too Late), and Martha Stewart (Martha). Showing no signs of slowing down, Cutler, 63, even found time last year to direct an Apple TV+ docuseries on the Los Angeles Dodgers’ victory over the New York Yankees in the World Series.
Perhaps that’s why Cutler sounds so positive about the documentary business in our conversation below, where he tells some pretty great tales about the inherent conflict between subject and director, and the tension that comes when having final cut while working with outsized personalities such as Stewart, Cheney, Carville and Wintour. The director explains why the genre has been able to withstand the ebbs of the industry, and the way aspiring filmmakers know they’re ready to become directors (and yes, that includes his advice on returning camera equipment to Amazon after 29 days).
So how’s the documentary game today?
I’m an optimist. I’m bullish. I’ve been a bullish optimist in the documentary business since 1992 with The War Room. But it’s always been a complicated business. Documentary filmmakers are outsiders to the entertainment industry, and we’re always coming at it from a side angle. The first day I met D.A. Pennebaker (known as “Penny” to friends), he said to me, ‘If you’re going to be a documentary filmmaker, you’ve got to have a bank robber’s mentality. You’ve got to travel light and always be ready to make a run for it,’ and that’s the case. It attracts and requires people who are incredibly industrious and crafty, not just as artists and storytellers, but also as businesspeople.
Do you think part of the problem in the early streaming era, people were cashing in, so they didn’t have to be bank robbers anymore? It became, for a while, much more of a factory, or a casino where the jackpots were constantly going off.
I do. If you have a 10-year perspective on the documentary business, you have one point of view. But if you have a 20- or 30-year perspective on the documentary business, you have a different point of view. In 1992, we were unable to sell The War Room. It was sold to October Films after many months of attempting to sell it for an extremely low figure, so low that I don’t want to say. Seventeen years later, we could not sell The September Issue at Sundance, despite screenings that sold out. I think we had nine screenings because the audience kept coming. We finally sold it to Roadside Attractions for the same amount we sold The War Room for.
Those films weren’t a slam dunk immediately?
To Roadside, it seemed like a slam dunk, but Roadside Attractions was one of those crafty, industrious distributors that didn’t have a lot of money to give you up front. They had to wait for the other people to pass, and those people did, and then they came in, and they saw the potential, and they got behind it in a big way. But, documentaries have always been risky, and that’s why I say, if you have a 30-year perspective on it, you remember a time when every film that went to market was taking a considerable risk. It required a certain amount of vision. In retrospect, it might seem like, ‘Who wouldn’t back the War Room, who wouldn’t back The September Issue?’ But none of the big distributors wanted them.
And you think of those as the moments when the theatrical documentary industry was relatively healthy.
It was robust. But it still required a certain amount of sturdiness. You knew you were in a risky place, and you hoped that you would also have a television sale that would back it up or something. But the business then grew. What we asserted in those days — that this is a popular art form with an audience, and we just have to reach it — was proven true by the streamers. I used to go to film festivals and run into Ted Sarandos when Netflix was a red envelope company, and Ted would say to me, ‘The War Room is one of the most popular films that we have. Our membership loves it. They love documentaries.’ So, it didn’t surprise me when Netflix started producing original programming that one of the first things they turned to was documentaries. And what do you know? Their membership loved it. During the bubble years, when programming was at its peak, not unlike premium scripted programming, premium documentary programming experienced a significant boom. Now we’re in the post-peak years, and like all other sectors of the entertainment industry, it’s challenging. But we know the audience is there. We know they respond to great work. We know there’s potential even in the theatrical space, even though there are bumps in the road. We see evidence with the films that attract audiences in theaters, but we also know that on streaming services, you can attract huge audiences to a movie like Martha. We’re told that between 30 and 40 million people watched that movie.
That’s got to be your lifetime theatrical audience combined times…
…Times multiples, yeah. But I mean, with that audience, what is called ‘the Netflix effect’ is real. But again, to people like me who’ve been believing in this notion that this is a popular art form, it’s not a surprise. Penny used to say, ‘If Robert Redford and Paul Newman can be movie stars, why can’t James Carville and George Stephanopoulos?’ The streaming services prove that thesis to be true.
I want to take a tour through the many branches of your career and talk about, like, what you learned from them. You started working in the theater, which is a unique path to the documentary world.
Well, I came to it honestly. I was a kid who grew up with two passions:
The theater and directing plays, which I started doing when I was a little kid in the neighborhood, and journalism, which was something I was always doing as well. My early career was as a theater director, and I was a Broadway baby. I worked with Steve Sondheim, James Lapine and Jonathan Larson. However, I also worked at National Public Radio with Ira Glass during his pre-This American Life years and learned a tremendous amount from him. I was doing those at the same time. I had an unusual career. I was in search of who I was going to be. Then, at around 30 years old, I had the idea to do The War Room. If you really think about it, the journalist approach and the theatrical storyteller approach are the two driving elements of the work that I’ve done. And so, I was able to combine those two passions in documentary storytelling and the verité idea —the notion that these films, as cinema, would engage an audience in the same way they respond to a scripted movie. This was, for me, a great combination of the two passions I have.
The basics of drama persist, despite TikTok, podcasts and everything else.
For me, they do. Look at somebody like Martha Stewart, what an extraordinary character with an extraordinary life story. And through that life story, there are incredible themes to explore. And at the same time that I’m making that film, Bradley Cooper is making a film about Lenny Bernstein. Another extraordinary story, of an extraordinary man whose life allows us to explore major themes. There was Oppenheimer. People’s lives can be great canvases and opportunities.
Do you have a better sense now of when you’re talking to somebody whether this person will work on camera, or is it just something you don’t know until you play it back?
The key question, and you’re tapping into it, is, ‘Are they ready to tell their story?’ Hard to think of a more human desire than to have our story told. Sitting down with Martha Stewart, the night I met her, and talking to her about her life story, the key is: Is she ready to tell it, and is she prepared to tell it with me?
I'm sure you must be approached by all sorts of notable figures who would love to have you document their lives. How do you sort through that?
It's about a connection between us, and in a way that’s ineffable. Are we going to be able to build trust? There was a great moment during the process of making The War Room, where, having watched the dailies, we went down to Little Rock and we said to James (Carville), ‘We want to make this movie about you.’ And he said, ‘Why me?’ I’m trying to get a guy elected president. Why on Earth would I ever let you do that? If you’re filming me, I’m gonna be worrying about my mom saying, Why are you cursing on screen?’ And, there was a long pause, and I said, ‘Penny, tell him why.’ But Penny said, ‘You know what, James, I can tell you why I want to do it, but why you want to do it, it’s your business, not my business. And that’s a personal thing.’ That has continued to be the question for me, whether it’s Anna Wintour or it’s Billie Eilish or it’s Martha Stewart or Elton John. Why are they ready? That’s personal, but that they are ready is key. And that I feel that there is an opportunity here for us to build a trusting relationship and make that connection, wherein they are loaning me their story to tell. They are trusting me to tell it, and they’re willing to give me final cut in telling it, which is going to be an active part of our relationship.
Everybody wants to tell their story, but everybody has a version of that story that they think is the version.
That’s right. Everybody would make a different film from the film that I would make. But there’s a reason why they’re looking in that moment to connect. Every experience has been different. I remember with Anna Wintour, the moment for me came when we were talking during our first meeting, and we actually were talking about final cut, because I said to her, ‘Listen, if we’re going to do this, I’m going to have to have final cut. Nobody’s going to take it seriously if you have final cut, and you deserve a film that people take seriously, and so do I.’ And without hesitation, she said, ‘Listen, my father was a journalist. I’m a journalist. I completely understand. That won’t be an issue.’ And I thought, ‘Well, fantastic.’ And then we carried on, continued talking about other things. Later that day, when I was reflecting on the conversation, I thought, Why did Anna Wintour talk to me about her dad? Who am I that she’s mentioning her father? When you look at the film, it encompasses a multitude of themes. But in terms of Anna’s character, it’s about the need to have her father’s approval. It drives that film, and it drives her.
Let's talk about Martha. This is a woman who’s had mountains of words written about her. She’s been studied and imitated. What was the story there that hadn’t been told already?
It’s true that her story had been told many times, but she had never told it. I first met her at a dinner in Montauk hosted by a mutual friend. I sat next to Martha and we talked, and it became evident to me that she was ready to tell her story. However, her story also became evident to me. It was surprising and counterintuitive. I didn’t know a lot about Martha going into that. I knew the broadest strokes. But as she started to tell me about her childhood and her upbringing, everything was kind of counterintuitive. She was not a child of privilege. She was very much a self-made person, one of six children. She had to model as a teenager in order to put food on the family table because her alcoholic father couldn't hold down a job. They had to grow their own tomatoes and trade them with people so they had food to eat. She was fully self-educated. I was almost immediately struck by the fact that her story, over the decades, was a story of American womanhood — even her trial and conviction and the fact that she was, as I came to see, selectively prosecuted by James Comey. That was a story of American womanhood, her success and her failure, and her rise again like a phoenix.
She’s very controlled and matter-of-fact, but you capture this emotion of coming right to the edge. How do you capture that tension?
That’s who she is. She presents as kicking and screaming, but she isn’t. She would say to me, ‘I’m dreading the interview. I don’t want to do it. I’ve never been in therapy a day in my life, and the last thing I want is for R.J. Cutler to analyze me.’ Instead of conducting the interview, we had a series of Zoom conversations. Some of the audio ended up in the film, but mostly it was an opportunity for us to discuss her story. We did it two or three times over several months. Then I went to Maine and interviewed her, sat with her, and had these longer conversations. By the time we got there, as much as she had resisted, here was an opportunity to tell the story. I just asked the questions and wanted her to be her truest self.
After you're done, do people get uncomfortable about what they shared?
Not in my experience. I can’t imagine any more vulnerable positions than watching yourself in a cut. I always show the film. This is another lesson that Penny and Chris Hegedus taught me. You’ve been trusted to tell this person’s story, show it to them, listen to what they have to say, and see how you respond to that. That doesn’t mean you’re giving them editorial control, but it means that you’re respecting the fact that the story belongs to them and they’ve put themselves in a very vulnerable position. It’s always important to me to be as empathetic as possible.
With Billie, she had my dream response. She said that until she watched The World's a Little Blurry, she had never believed that she could be seen the way she sees herself. So that was wonderful. Martha felt like she looked older than she wanted to, and didn’t like some of the things she was wearing.
Did you show The World According to Dick Cheney to Dick Cheney?
We went to Wyoming, to Liz Cheney’s cabin, and Lynn Cheney (Dick Cheney’s wife) was there, and the vice president was there. And before we screened, I said, ‘You trusted me to tell your story, and I’m here to hear what you think about what I’ve made.’ And believe me, they were not happy, but we had one of the most interesting conversations I’ve ever had, with the four of us about the film. When it was over, we didn’t make any changes to it, and after talking about it for an hour, Vice President Cheney said to his wife and daughter, ‘Look, it’s R.J.’s film. I would have made a completely different movie.’ And so there you go. He’s a guy with a thick, thick skin, but it’s always part of the process.
Your big topic has been this relationship between people’s public and private selves. How do you feel about that? Getting to know all these extremely high-profile people and going through that.
I wouldn’t have described that as my big theme, but I will say that I certainly know what you’re talking about. I’ve never been particularly interested in the public version. I’m incredibly interested in the real person. I’m interested in the child of their parents. I’m interested in the child who grew up to become this person who has pursued greatness, in some ways motivated to overcome certain things. What can their life story tell us about our own life stories? Martha is a film about the little girl whose father slapped her in the face when she came home and said that she was in love with a man who was the opposite of her father. The film about Elton John (Elton John: Never Too Late) tells the story of a great man who has lived a life in search of elusive happiness and has finally found it late in life. He is now confronting mortality as he ends his public performing career. There’s no question that the elements you’re describing play into this. How does that search for greatness manifest itself in a public persona? And certainly, what is the tension between public and private? However, I’m not particularly compelled by celebrity or public, just as a subject. It’s almost beside the point.
You made not one, but three films about politicians. We are in an intensely political moment here. Do you feel compelled to make a film to speak to this moment?
It’s a great landscape for storytelling, the world of politics. We were discussing the theater, and many of Shakespeare’s plays feature politicians as characters. And it’s an incredible landscape for storytelling.
Are you tempted at this moment to do another political film?
The term political film is interesting. Do we mean a movie where politicians are the characters in the film? If the right circumstance came up, I certainly would be very compelled. The world has changed since The War Room, A Perfect Candidate and The World According to Dick Cheney. One of the significant changes is that every contemporary politician has their own video team filming them. What I’d love to get my hands on and we will have the opportunity, I think, at some point, is the White House video tapes of an administration. Somebody was filming Barack Obama every day for eight years. There was always a camera in the room. I don’t know if there was a camera in the Situation Room, but I’d like to find out. That’s going to be very interesting, not just for historians, but I think for verité filmmakers. It’s going to be found footage in a really exciting way.
Do you have your eye on a dream topic at the moment?
Not for me at the moment. I think all Americans are very eager to understand what’s happening with their government right now. As a citizen, my level of inquiry and concern is exceptionally high. As an artist, I’m always looking for stories that are about our moment in time in the world we live in.
Right now, I am making a film about an operation called Camp Century that the Kennedy administration undertook in Greenland in the early 1960s when they informed the Danish government they were building an underground city in Greenland that would basically be a kind of monitor of climate. Instead, it was really a military base with missiles aimed at Russia. The Danish government was unaware of this, and the U.S. government constructed an underground military base. For various reasons, they soon abandoned it. Basically, they left nuclear waste because it was also a nuclear-powered underground city. Their secrets were buried in the Arctic ice, and they thought nobody would ever see it, that the ice would be here forever. With climate change, the ice is melting. Geopolitics is changing in terms of the strategic military value of Greenland. We know that the current administration is discussing a more involved relationship with Greenland, but it is not the first. This has been going on, in fact, long before the Kennedy administration. You can date the understanding of the strategic value of Greenland to American administrations back to the late 1800s. We are not only telling the story of what happened in the early 1960s, but we are also following the story of what's happening in Greenland right now. I guess you’d say that’s a story about a political point of view, about politics, but it’s a classic buried child story.
What is it like making films and running a company right now?
Another thing that goes back to the theater model. I think of myself in the tradition of the artistic director of the theater company. I have this great company, This Machine, where I'm working with all of these wonderful people. It’s a producer’s company. About a third of the work we do I direct, but we’re also a home for artists. We have a film that premiered recently, titled Karol G: Tomorrow is Beautiful, about the Colombian musician Karol G, directed by Cristina Constantini. A great filmmaker, a beautiful film that’s a big success on Netflix. We have another movie, directed by Ting Poo, about Lee Soo Man, the man who invented K-pop, which is a big hit on Amazon. It tells the story of a visionary who, 40 years ago, had an idea that would become K-pop. It’s wonderful to run a company because I get to support other filmmakers during a challenging time in the documentary business. As I mentioned, the model is a regional theater company that has numerous shows scheduled, is planning for next season, and so on. So I love it. I’ve always loved producing. I’ve always loved having a company. Since I was a teenager, I had a little theater company in the town I grew up in, and that’s what running a company is like for me. It’s a great place for artists to gather, in my opinion.
Is raising money harder these days?
My perspective is that it has always been challenging. All opportunities come with a cost. If the opportunity cost is what you want, you’ve got to decide if it’s right for the film. If you’re a producer, you determine if it’s right for the filmmaker. As a director, I have to decide if the situation is right for me as a filmmaker. Will I take less money to make the film and then sell it later, because I’ll have more freedom to make the film that I want to make? Or is it more important to know that we’re going to be secure in this situation, and we're making the film, and we have our network partner or our streaming partner, and we’re going to hold hands together and go down the road together? From the beginning, every project requires its own analysis and set of calculations. And then you make a decision, and you carry forth. You’ve got to rely on your allies for sound advice and wisdom. You’ve got to really remember to ask for advice and perspective. It’s why my This Machine business partner Elise Pearlstein is so great, because she brings so much wisdom and experience from years working at Participant Films and her whole career.
Final question: What advice do you give to someone just out of school who wants to go into documentaries today?
I don’t think I would encourage going to film school. The great thing about film school 20 years ago was that you could easily obtain the necessary equipment. But now, here it is (holds up his phone). There’s your camera, better than any camera you could have gotten hold of 20 years ago. There's your editor. Your editing facility is right here. You can edit it here. And if you need higher-stakes equipment, in the spirit of the bank robber mentality, buy that equipment from Amazon, use it for 29 days, and send it back to them. They’re happy to take it back. They’re not going to be upset with you. They say you can use it for 29 days and return it. And make your first movie, so that you can make a lot of first movie mistakes, and then make your second movie, and then make your third movie, which is going to be even better than your second movie, because you’re learning. And that's my advice, absolutely, to anybody who's in any creative pursuit. Make a film, and God bless you for doing it.
I’ll tell you one last Penny story. We were finishing up The War Room, and I had the occasion to meet Pat Riley, who, at the time, was coaching the New York Knicks. And I was so thrilled. And I said to Pat, ‘We should do a film like The War Room about you.’ And he said, ‘Oh, no, no, no.’ And I was like, ‘Come on, I'll bring in D.A. Pennebaker and Chris Hegedus to talk to you.’ And he said, ‘Well, I’m always happy to have a conversation.’ And I went to Penny, and I told him. I said, ‘Great news! We’ll meet with Pat Riley of the Knicks.’ And he said, ‘I thought you wanted to be a director.’ And I said, ‘I know, I do.’ And he said, ‘You told me the next thing you want is for you to direct a movie.’ And I said, ‘Yeah, but there’s this great opportunity.’ And he said, ‘Listen until you wake up screaming in the middle of the night, you’re not a director. And you’ve got to do that and decide if that’s what you want, because if you don’t do it, you’ll never know.’ And what great, generous mentorship advice he gave me in that moment. And so I would say that also to an aspiring young filmmaker: wake up screaming and see if it’s for you.
R.J. Cutler’s Curriculum For Hollywood
I asked each Maven if they could require everyone working in entertainment to watch or read a few movies, books, articles, dance pieces or anything they liked, what would their required pieces be? Here are Cutler’s picks:
Sullivan’s Travels (1941, Preston Sturges)
Network (1976, Sidney Lumet)
All That Jazz (1979, Bob Fosse)
You’ll Never Eat Lunch in this Town Again (1991, Julia Phillips)
Final Cut (1999, Steven Bach)
