Why It Was Worth The Struggle To Toss A Hero Take On ‘Killers Of The Flower Moon’ To Unlock Dark Truths & Resonant Performances Like Lily Gladstone Breakout Turn

Since Jack Dawson made him a top global star in Titanic, Leonardo DiCaprio has largely avoided the straight hero route in favor of shaded, conflicted characters in films from The Revenant to The Departed, The Aviator, Gangs of New York, The Wolf Of Wall Street, Once Upon A Time…In Hollywood, and others. But he’d never gone to the degree he did on Killers of the Flower Moon. The first version of the film had almost everything going for it: the David Grann bestseller bought for a shocking $5 million by Imperative Entertainment, a script Eric Roth wrote, and the first teaming of Martin Scorsese, DiCaprio and Robert De Niro, the latter going mano a mano for the first time since This Boy’s Life established a teenaged DiCaprio as the young actor to watch.

A green lit script that had DiCaprio playing the incorruptible Texas Ranger-turned FBI agent Tom White who ends the Reign Of Terror murders that decimated the murders of oil rich Osage tribe members in Oklahoma in the 1920s. Until DiCaprio, Scorsese and De Niro decided it didn’t capture the Osage side and perpetuated the “white savior” narrative that has been a staple of Hollywood westerns forever. Here, he explains why this epiphany that set back the project years was so worth it.

DEADLINE: You have this huge package, with Martin Scorsese directing you and De Niro chewing the scenery in a proper crime story. You’d normally rush into production such a can’t miss vehicle. And you stop the bus and say, where’s the heart in this? It delays the film for years and leads it from the well worn white hero path and down a darker but more truthful road where you play Ernest Burkhart, convicted of trying to murder his Osage wife for her oil money. It’s laudable to want to make an audience feel something other than deja vu, but how hard was this overhaul? Apple replaced Paramount as financier, but we have all seen movies lose momentum and die.

LEONARDO DICAPRIO: It was hard. In a lot of respects, the ship had already sailed, with the Tom White version. We were gearing up to make that movie. Marty uses the word complicity in talking about this film.

DEADLINE: That wasn’t in the first version and nagged at you?

DICAPRIO: What was our complicity in all this? What was our responsibility? What is our responsibility still to this day in the relationship to Native Americans, the ownership of their land, their treaty rights? What role do we play? And I’m not going to say that that was the onus for the change. We were ready to go before The Irishman. We had two major round table script meetings, when we were developing the book. We optioned it, and were very excited about creating Tom White as an interesting multifaceted character, which he was.

Leonardo DiCaprio, Lily GladstoneMelinda Sue Gordon / © Apple TV+ / Courtesy Everett Collection

But the approach was so much from the idea of a forensic whodunit, with a twist. Tom White was fascinating in his search for details, but at the end of the day, De Niro was playing Bill Hale. I don’t know what the mystery would’ve been, from the onset. It got us to, where’s the actual drama? Where’s the inter-relationship between the two characters? It got to a point where, I, on a personal level, wasn’t feeling much. It was fantastic to see the new techniques, like watching White Heat in a lot of ways. Remember, he was driving around with that satellite car, the FBI or the cops trying to figure out how to track this criminal using technologies that are new for the era, how they’d talk about the bullet holes and the new cutting edge ways that the FBI were solving crimes.

And then we also saw the FBI’s version of the Osage story, at that time, and it had a pretty deplorable depiction of Native Americans, in particular the Osage. It made a mockery of how they spent their money and their lavish lifestyles, and how the FBI came in and saved the day. All that was in the back of our minds. But the real catalyst was this one moment, the culmination of everything that happens in Killers of the Flower Moon, which is Molly, and Ernest on the witness stand. It was shocking to believe that this relationship was real, that it actually existed, that these people did love and care for each other, and had an entire family. And then he systematically tried to eliminate her entire bloodline for the corruption of the American dream and the thirst for wealth and greed.

And here he is, admitting this to her, getting a life sentence, flip-flopping back and forth. And she’s got to look at him on the stand, and admit that her whole life with him has been a fraud. And that was what gave us an emotional reaction, immediately afterwards. It seemed like almost a preposterous idea. If you look at the depiction of Hale and Ernest in the FBI [version of the] story, they’re like sniveling cowards, crying because the FBI finally cracked the case and they were both in trouble. We kept on coming to the idea that, I didn’t feel anything, emotionally. Marty agreed.

We then started watching films again, like The Heiress, and particularly A Place in the Sun, to look at how a twisted bizarre love story and the corruption of that American dream could all go awry. And Montgomery Clift’s relationship with Elizabeth Taylor and his wife and what he does and what he sacrifices. And we started to say, well, what if this was just in the household that would lead us to understand more of Osage culture, the clash of these two cultures. During such an insane, bizarre period of time because there’s an association with Native Americans and white people and the whole genre was completely flipped in this movie. Here you have the Osage with this massive amount of wealth…it was like the gold rush back then, and it attracted this white opportunistic vermin that came in trying to reclaim Native American land. And right nearby, the same thing happened with African-American wealth, with the Black Wall Street massacre in Tulsa. Oklahoma was this powder keg.

So Marty just said, I’m going to go do this other movie. We don’t have a script. And we pitched another version. It was not met with rocket fuel enthusiasm when we said that we were going to try this other idea. And Marty had to say, ‘hey guys, look, trust me, I’m going to make this happen. I’ve done a couple movies before.’

DEADLINE: Not many filmmakers could do that.

DICAPRIO: We took the chance on it and I’m really glad we did, because we got into the heart and soul of this very bizarre, twisted relationship, which is a symbol in a lot of ways of how incredibly sadistic some of these people were in trying to take advantage of the Osage during that time period.

DEADLINE: It wasn’t like the FBI comes in and there are 10 possible suspects doing these murders, so it would’ve made it more like the time De Niro played Capone, up against Kevin Costner in The Untouchables. You knew going in who was terrorizing Chicago with a crime spree. That’s been done. What’s the closest movie you made where you and your creative cohorts decided you were going down the wrong road and you turn the whole movie on its ear?

DICAPRIO: This was a first for me, where we completely flipped it., I spoke a lot to David Grann, and he kept saying was that Ernest was a very malleable character. He was highly under the mental influence of his uncle. The real banality of evil, as Bob calls his Hale character, is his lust for everything around him. And how he assimilates himself in the Osage community. It was so beyond detestable, but Ernest did develop this relationship with Mollie. That was a real one. When we saw The Heiress, it started to all click with Olivia de Havilland. And then we met Lily, we saw her face. She has this incredible face that is so endearing to an audience and you feel so much for her, and so the tension in the movie is not about solving the crime, it’s about what’s going to happen with this relationship.

Robbie Robertson’s score really drives that home too. When is she going to figure this out? It gave me anxiety in reading the book, saying, what is going to happen here? Because there’s a symbiotic relationship between the two characters. The Osage being deemed as incompetent at the time, didn’t have access to their own wealth, the rights to what they own. All these opportunists then came in and took advantage of this and said, ‘okay, now we’re in a married structure, we’re a family unit. We can be Americans.’

The one very touching thing, because I couldn’t figure this [relationship] out myself, but when we went to visit the Osage elders. They said to us, when you marry or become a part of our family and there’s a wedding ceremony and you are connected with one of us, you are now Osage. You are trusted one of us. You are embraced like one of us. You’ll become a part of us. And that was something that I think Hale and Earnest obviously preyed upon. They knew that there was a trust factor there that they could take advantage of.

DEADLINE: And Ernest was too weak to resist his uncle. Your dynamic with Bob De Niro started on This Boy’s Life, after which Bob suggested that Marty keep an eye out for you. Did you and Bob stay in touch? How much of a mentor was he for you? You told me you were a kid used to acting up, and you saw in him how a real actor behaves on a set.

DICAPRIO: He has been huge, one of the most highly influential people in my career, and mostly in the sense that he leads by example. When you’re 16 years old and you walk onto that set and you see the way he commits to his characters, the way he improvises, the way he embodies the soul of these characters that he takes on, and his filmography as an actor…it was never a situation where he sat me down and told me the rules of the game. But that actor/director collaboration with Marty is still, to this day, the most highly influential for me as a young actor watching movies. And for most of my friends who are actors, it is the high bar. And then to come back 30 years later? We were both in Marvin’s Room, but we didn’t act together in that.

KILLERS OF THE FLOWER MOON, from left: Robert De Niro, Leonardo DiCaprio as Ernest Burkhart, 2023. ph: Melinda Sue Gordon /© Paramount Pictures /Courtesy Everett Collection

DEADLINE: How did it feel after all those years?

DICAPRIO: Doing it with Marty felt like a situation where this giant concentric circle happened where we developed this script altogether with all of us in mind. I can’t really put into words what it meant to me. Marty said it very well. It just felt right, and it felt easy. I joke with Bob about this a lot, but besides all my character work, the dynamic of our relationship was really linked a lot for me to This Boy’s Life and the oppressive, manipulative father figure. And it’s almost like my character from that film just grew up and maybe lost a few brain cells, and fit right back in those shoes, being manipulated by this older abusive father figure. One of the best memories I’ll have from that whole dynamic was Marty being in Oklahoma for eight months, when he really didn’t leave his house.

THIS BOY’S LIFE, Leonardo DiCaprio, Robert De Niro, 1993. ©Warner Bros./courtesy Everett Collection

We still had issues with Covid, things like that, though we’d just gotten the vaccine. But he was locked up, committed to telling this story the right way, obsessive in a way that I’ve never experienced because he wanted to tell it right for the sake of the Osage. He really listened to their viewpoint on how all of this happened. Not to go off on a tangent, but he didn’t want to make the FBI hero story. The FBI took years and years and years to finally come to Osage territory. They basically had to get paid off. They had to have a delegation of people go to Washington to get them to come figure out what was happening with these murders that were part of their jurisdiction, a part of their own responsibility that they were in essence ignoring.

But for all intents and purposes, the relationship between Hale and Ernest culminated in that jail sequence. And I don’t know if you’ve heard it before, but we spent I think four weekends and we stayed in Oklahoma. We didn’t leave town and spent the entire day, every weekend, talking about this scene and how to end this relationship between these men because we were dealing with the remnants of the old screenplay.

DEADLINE: How was it different?

DICAPRIO: It was this massive confrontation, this heroic sort of reaching through the jail cell, strangling his uncle. And we realized that…I watched Bob and Marty distill it, slowly, down to the truth of what a real father-son relationship would be like. Which is [Ernest] feeling afraid that Hale would be disappointed in him. Afraid of his uncle realizing that he’s not the man that he thought he was. It’s a much more quiet, very subtle thing. This ‘I have to do this, dad.’ ‘Well, God bless you, son. You’re still making a mistake, but God bless you, I love you.’ And that was one of the most surprising things, and it was watching both of their instincts. Because when I work, I like to figure out every different possibility and burn them out, and we kept going, distilling it further and further down to the truth of what an abusive relationship like that would be like. And it’s a scene that I’m very proud of, and it could have only happened with those two men in the room.

DEADLINE: With an economy of words and these incredible brown eyes, Lily Gladstone grounds this movie and she hovers over it like a conscience. When Marty was looking for Mollie, what made her right, and why was she right?

DICAPRIO: I knew it when we left the Zoom [meeting with her] because of the look in Marty’s eyes. I had essentially gone and done another movie. We quickly got on this hourlong Zoom. I think they had spoken before, but in a lot of ways you could see she was so representative of this woman and not only from a moral but a philosophical level, her speaking about relationship between Native Americans and the United States government, and who this woman was and her own heritage. She just embodied it immediately, in that Zoom. And there was no reading. It was us, asking her questions and trying to understand on a deeper level what this relationship was, and who she was. And at the end of it, Marty just had this look at his eye. He said, ‘okay, Rick [Yorn],’– that’s our manager – ‘hire her.’ I’m like, whoa, really? Marty? We didn’t read. Are you sure you don’t want to read? He’s like, ‘no, no, no, no, no. I don’t want to mess around. This is it. She is Molly.’ I said, okay, great. And boy, was she ever.

Lily Gladstone interview
From left: Leonardo DiCaprio and Lily Gladstone.Paramount Pictures/Everett Collection

DEADLINE: We read all the time about crimes of passion within families. But it still seems hard to fathom a man who loves his wife and their kids and her wealth would be complicit in slowly killing her for her entire fortune, and that she would be so blinded by his love that she lets him do this. What kind of conversations did you and Lily have so that the two of you could understand exactly how something like this could happen and how you would interact together?

DICAPRIO: It was all shaped basically by the ability to speak with the Osage, the direct descendants. A multitude of people came up to me and said, that was a real relationship. There was real love there. He really loved that woman. I’ve said, what is one’s interpretation of love? Because this doesn’t seem like love to me. This doesn’t seem like it could even be possible. But you start to look at the fact that he started to realize slowly towards the end that it’s one thing to have her entire bloodline disappear, and him sitting on this wealth that came from his relationship with Molly. It’s another then to start realizing that Hale would stop at nothing to probably want to take her out next. He then flip flops. Everything is true about this story, and I’ll get back to one part which we had to interpret, but everything is in the court documents, stories from direct descendants, from David Grann’s research and what really happened.

KILLERS OF THE FLOWER MOON, from left: Lily Gladstone, director Martin Scorsese, on set, 2023. ph: Melinda Sue Gordon / © Apple TV+ / Courtesy Everett CollectionMelinda Sue Gordon / © Apple TV+ / Courtesy Everett Collection

This man at the end of the day realizes that his wife’s going to [die], and he turns himself in and he gets a life sentence. He turned himself in. He doesn’t serve all the time, but goes to prison and then comes back to Osage territory, an outcast who lives in a trailer with his brother. Paranoid that people are going to take him out. I got to speak to his niece who was there. She told me she asked him and Byron his brother exactly what happened when they got drunk every Christmas. And Byron took her to the location, showed her where Anna Brown was murdered, and how it happened. And then Ernest was insistent that he loved [Mollie] and would get adamant about it. That she was a good one, which is what he said in the only piece of video footage that I saw of older Ernest in, I think his late eighties in a trailer park. Saying that [Mollie] was a good one.

DEADLINE: So maybe this was a redemptive moment for Ernest, giving himself up so his wife could live, even though it was he who was slowly poisoning her at home at the behest of his uncle…

DICAPRIO: But there was one thing that we had to figure out, which I became quite obsessed by, because it really gets distilled down to what he was capable of doing. What was in that poison that he was giving her? I called it poison, but it must’ve been a concoction of something that was making her high as well as slowly making her sick because she was confined to his care for one year. And as soon as the FBI came, she got better. We spoke to every doctor imaginable. We talked about what could be done. Is this some sort of life support that he’s giving her? Not quite letting her go completely, but keeping her just well enough to get rid of the heat from the FBI, which had come into town trying to figure things out. We also added the idea of him taking a little bit of himself, out of the guilt that he feels. That was the only thing that we had. There was no historical record, no admission in court as to what he did. And he never admitted to doing any of that. But you look at the Shoun brothers [the doctors depicted as prescribing the poison diabetes injection cocktail, and helping to cover up Hale’s other murders], you look at the evidence, you look at how sick she was during that time, and the fact that she got better after she was in the FBI care, and we kind of put the pieces together.

DEADLINE: Lily grew up on the Blackfeet Reservation in Montana and calls herself “just a res girl.” You could imagine her dreams of being in a big Hollywood movie. There she is, playing Leonardo DiCaprio’s wife, acting scenes with you and De Niro for Marty Scorsese. How do you help her feel comfortable and not like she’s in some surreal and intimidating dream?

DICAPRIO: There was none of that. To us, it was an immediate partnership. That’s how she conducted herself from the initial Zoom call. And when she came on board, you kind of felt that she was channeling something from her own family tree. She talks about her own grandmother because the moment she came on set was you kind of felt that she brought all that history, all her heritage, the pain, but in addition to that, the heroism and dignity that she must have channeled from her own life and her own relationships. She owned it the moment she came on set. So much so that I believe Marty and I were really looking towards her to understand the complexity of this very unbelievably twisted relationship that they had. We were on this, how she could stay with this man, how she could stay with somebody who, from the outskirts would seem is so obviously taking advantage of her?

KILLERS OF THE FLOWER MOON, Leonardo DiCaprio (left), Lily Gladstone (center left), Robert De Niro (standing, left), Sarah Spurger (standing, right), 2023. © Paramount Pictures /Courtesy Everett CollectionParamount Pictures

I keep talking about the scenes. Again, my character is a very unreliable protagonist, so you don’t know. And we were playing with that the entire time we’re doing this movie, how much are we going to reveal to the audience what Ernest actually knows, or how much are we going to show that Ernest is complicit from the beginning? Is this a slow burn? Are we revealing everything from the beginning? Is it something that the audience I’m going to fully understand, that Ernest is a part of this, or is it going to be something that we reveal later on?

But for her, she just sat in this amazing sort of truth, and we looked to her to understand this relationship in a lot of ways, and she brought so many different nuances to the entire narrative. I keep talking about the idea of the trickster and Native American stories, and her bringing up what a coyote is, and her identifying very early on that I am a coyote. And that’s a very complex thing to bring up for a relationship like this. You can sort of die on the sword with a theme like that, but that’s what I love about her saying that to Ernest right off the bat. I know who you are, I know what you’re after, but still I can see that you want to settle down. I see that you want to have a family. She’s living in an environment where no one is to be really trusted. So in a lot of ways, she chose the one that she felt she had the most connection with. There was something in him that she believed in. And then to further that, the scene that I immediately responded to the most when I first saw it is the scene with her and all her sisters.

DEADLINE: Where they playfully romanticize these ruffian suitors, while acknowledging they might just be courting them for their head rights…

DICAPRIO: All that stuff was improvised, using these animal analogies for all the different white men that were surrounding them in the Osage community. Well, this one’s a rabbit, this one. I was like, that is so complex and beautiful that these women are laughing at this, joking around and have a real kinship and sisterhood and lightheartedness in this incredibly bleak environment. Lily brought all that stuff and more, and she helped me understand too what this relationship was

DEADLINE: You are prepping your next movie, starring with Sean Penn and Regina Hall in this untitled film with Paul Thomas Anderson. It’s a big budget Warner Bros film with higher commercial ambitions than PTA films usually have. That is a straight theatrical release, but I recall that on Killers, it was very important to you, to Marty and your manager and the film’s EP Rick Yorn that it start as a global theatrical release with P&A, rather than a limited theatrical play before going to a streamer platform like Bradley Cooper’s Maestro at Netflix. Killers opened on the Apple TV+ platform yesterday and it doesn’t at all seem the streaming customers resent being second. They’re aware of the film because of the P&A spend an eager to watch at home. Might this be the template to handle this collision between streaming and the traditional theatrical business for ambitious big budget films?

DICAPRIO: Unfortunately, I don’t know if, unless you have an obliquely commercial movie, many are going to get that opportunity. I can only speak on the first personal level. There are certain filmmakers out there that, to me, it’s a transcendent experience to see their films in a theater, and it’s how theaters are going to survive. I have a mixed view on this. There are a lot more opportunities for a lot more people, not only filmmakers but actors, to tell stories than there was 10 years ago. They would be impossible to get financing. We’re seeing a lot more of that now. So that’s a positive. But I know, seeing 2001: A Space Odyssey on my television at home, and watching it in restored Cinerama at the theater, or even watching The Irishman twice that way, was when I understood how different the experiences are. Marty released that on Netflix, but I got to go to two different premiere screenings. To feel the energy of the audience and the excitement and the enthusiasm to watch Joe [Pesci] and Bob together again in that relationship, with all the subtleties in their faces, projected on a screen that was 50 feet tall…and then watching it at home. These were two completely different experiences.

THE IRISHMAN, from left: Jesse Plemons, Ray Romano, Robert De Niro, Al Pacino as Jimmy Hoffa, 2019. © Netflix / courtesy Everett Collection

Watching it in the theater was just incomparable. I just felt a lot more, I don’t know how else to describe it. So what can I say other than hopefully more of those films have that? That doesn’t mean limit it to a handful of master filmmakers. I mean indie filmmakers too, who put their hearts into a movie that is supposed to belong in a dark room. I hope they still gets those opportunities. But the world is changing, every day, and there’s a shift to everybody watching things at home now.

DEADLINE: Everyone thought you’d play Dirk Diggler for PTA in Boogie Nights. Instead you did Titanic, which worked out pretty well for you. You were mentioning that for you and Marty and Bob, Killers closed the circle. Is that also the case with you and PTA?

DICAPRIO: I’m really excited. I haven’t worked with him yet, we’ve only had discussions, but I’ve known him throughout the years, and he is so committed to his ideas and his own vision. And when you work with somebody that is so diligent about what they want to do and how they see things, it takes away half the battle for you. It takes away half the guessing game. And you can focus on the craft and what you have to do. But man, he’s a writer director, an incredible storyteller and not for one moment has he sacrificed what he’s wanted to do as a filmmaker on screen for anyone. And isn’t that a rarity?

DEADLINE: So in this PTA movie you won’t have to get under the hood and rebuild the motor like you did on Killers of the Flower Moon. From making you want to direct down to being more selective and insisting that a script have truth and heart before you star in it, what do you take away from this experience as you continue to evolve as a storyteller? 

DICAPRIO: I don’t know about directing. But as a younger actor, I don’t think I would’ve done what we did on Killers. Well, maybe that’s not true. I remember having discussions on Gangs of New York about the screenplay. But this was a culmination of many years of working with Marty, and trusting our instincts. And if something is bothering you from the onset while making a movie, it’s going to come up again, rear its head years later when the movie’s actually finished. There’s no way to escape those things. Some of these things come to me in weird dreams. I won’t get into specifics, but I do know that there are moments where you have to just throw the baby out with the bath water, so to speak, and start all over again if it doesn’t feel right. And the experience that I’ve had with Killers…I don’t know if we would’ve gone there had Marty and I not had this longhand as he likes to talk about it, as far as our relationship is concerned. That made us willing to completely throw out a concept because we didn’t feel like it got to the heart of what we wanted to say. We did it and looking back, I’m proud of that moment for the both of us. Because more than anything, it gave us an opportunity to tell the story of the Osage in a much more profound and truthful way.

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