I​​n Highlight Reel, Awards Insider speaks with some of this year’s most notable Oscar nominees about their entire body of nominated work. In this entry, we speak with Women Talking producer Dede Gardner, president of Plan B Entertainment.

The first woman to win two Oscars for best picture—and one of the most decorated producers of the past decade, period—is well aware that her latest nominee, Women Talking, has faced a bumpy awards journey. Dede Gardner has been here before, after all, passionately backing a film beloved by critics and of the kind of rich social import that the Oscars usually love to recognize, but which still meets an inescapable resistance from certain corners of her industry. Sometimes this dynamic translates to low box office receipts and uncalled-for snubs; other times, the naysayers are proven very wrong, like the two times Gardner has accepted the best-picture trophy for true underdogs. She’ll never forget the advice her producing partner, Brad Pitt, gave her shortly after she joined his company, Plan B, nearly 20 years ago: “Movies have a long shelf life, and you and I didn’t necessarily find our favorite movies in the theater. So let’s just keep doing this.” 

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Along with Pitt and Jeremy Kleiner, Gardner has helped steer seven movies to best-picture nominations since 2012. She was part of the first winner directed by a Black director and with a majority-Black cast (12 Years a Slave) and the first LGBTQ+-focused winner (Moonlight). The other nominees on her list range from star-studded blockbusters to intimate character dramas, a showcase of her interest in—and ability to closely collaborate with—a range of filmmakers. Speaking with Vanity Fair, Gardner reflects on her remarkable Oscars run, culminating in her contender this year, Women Talking, written and directed by Sarah Polley and produced with fellow Oscar winner Frances McDormand.

Vanity Fair: I wanted to start by going back to near when you started at Plan B, and particularly a year that I love, 2007, that of A Mighty Heart and The Assassination of Jesse James by the Coward Robert Ford. This feels like the moment that a mission statement was informally established.

Dede Gardner: Yeah, it’s a meaningful year to me. I was pretty new and I loved both those movies a lot. At the end of that year, the truth is nobody went to see either of them really. I was like, Oh fuck, is this going to work? Do you know what you’re doing? I had been at a studio for eight years, so was dialed into the primary adjudicator: Did people go, did they make money, were they profitable, et cetera. But Brad said to me—I’ll never forget it, actually—“I could not be prouder of this year.” We didn’t even know each other that well then. I remember thinking, Really? He’s like, “Look at the degree of difficulty and the exquisiteness of the films and the dedication. That’s what this should be about.” That’s a pretty great way to start a run at a company.

It does make me think of a movie like The Tree of Life, which is such a beautiful movie, one that is pretty unforgettable, but also ambitious and complicated. Was that a kind of guiding principle here? Given its structure and how long it took to make, did you know what you were getting into?

I think we had a sense. I mean, you certainly knew what chapters were intended; you were aware of the breadth of his vision, for sure—that they were really in conversation with one another, that there was going to be this majority that we would go shoot in Texas. And then when Sean [Penn]’s character comes in, and that’s much more abstract and much more urban. We knew what he was plotting with the visual effects in terms of the birth of the universe. Even that final chapter, we had a sense.

So what surprised you?

Inside the guardrails, which were legitimate, it was a really fun shoot because Terry [director Terrence Malick] and Chivo [cinematographer Emmanuel “Chivo” Lubezki] just wanted to be able to shoot. It wasn’t like they wanted to shoot 360 and maybe be in that house—it was, maybe be in that house, and maybe it would be up and maybe it would be down. Terry would hand new pages to the actors. It was fluid inside a very structured box, and I’d never done anything like that, but we built it to be able to do that. We were in a small town in Texas outside of Austin called Smithfield, and there were no trailers and there were no trucks. We would show up every morning and watch Terry and Chivo just go, “What should we shoot today?” So as long as he finished, we had X number of days, but within those days we could—the elasticity was so profound and marvelous. I think it took the actors a minute to understand that elasticity, but then once they realized, Oh, this is the greatest playground ever, everyone was really into it.

This movie was a watershed moment for Hollywood and the Oscars in so many ways. We have a few of those to talk about, in terms of your résumé. The genesis here, if I have it correct, was Steve McQueen essentially asking you in a conversation, “Why hasn’t there been a film made centered on the institution of slavery?” Do I have that right?

One hundred percent. Jeremy and I were at a breakfast with him in New York, and he just said, “Well, I don’t understand, why doesn’t this exist?” And we said, “Let’s try.” It was a long, long incubation process of a lot of research, a lot of reading, a lot of attempts at, “Are we going to create this?” Just a lot of thinking. It was Steve’s wife who found the book, and the minute she found it, he said, “We have it. This is the structure, this is the narrative,” and then we began.

Yeah. Being the first with anything—in this case a film of this topic, made on this scale—obviously comes with an enormous amount of responsibility. Steve is the filmmaker, but you are the producer on this project. So how did you absorb that? What did that feel like, and what did your work along those lines look like?

I didn’t really think about that, to be honest. I had so much faith in him, I saw who wanted to be a part of it. I don’t have that much interest in making movies that have been made 100 times before. And you never know, right? You just don’t know. There’ve just been movies that go the distance and someone says, "No one’s going to see that,” and people say, “Everyone’s going to see that,” and no one sees it. It is still a little bit of a mystery.

Did you hear those kinds of things with this movie, a kind of resistance not only to making it, but having the confidence that it could find that kind of audience and sustain itself?

I think there was amazing support from some people, and there was resistance from others. I’m going to thread that needle. [Laughs.]

Fair enough. What do you remember about Oscar night? This was your first win. It was a historic moment, and the culmination of a pretty remarkable campaign.

It felt super lucky. The thing about the Academy recognition is that it ensures that more people will see the movie. That’s really what I hold on to. In the case of 12 Years a Slave, it opened up avenues that far exceed the film business. The book entered curriculum in different schools—the kind of concentric rings outside of a movie’s life inside of Hollywood. They’re really thrilling to enter and be a part of, trying to get a ringside seat in how the movie is interacting with the culture or how it could.

From what I remember, it had a rousing AFI premiere, got incredible reviews. And then there was this strange underperformance across awards season, with various controversies and various missed nominations, relative to what the movie probably deserved.

I agree. But here we are again with Women Talking.

I was about to say that: From my perspective of the movies we’re talking about here, it feels like Selma and Women Talking are your two hardest-fought best-picture nominations.

Hardest fought and not, I think, properly nominated in the categories they should be. I mean, there’s not a question in my mind that Ava [DuVernay] and David [Oyelowo] should have been nominated. Not even a question in my mind. That’s a pretty stark reality. I also believe this is true: I don’t think it’s random that they’re both female directors.

Right. In the case of Selma, there was all this litigation over what felt like every historical detail in that movie being picked apart to death, which I don’t think happens to every biopic.

No, I agree. I found the level of scrutiny bizarre, outsized, and not appropriate. And it felt entirely reactive and without any thought for what she actually had crafted, which was very deliberate and very careful and very precise. And then there were LBJ enthusiasts who wanted to put their stake in the ground. It just came from all sides. But even so, I don’t think that should have denied Ava or David those nominations, and they were.

Even so, this was a real turning point for Ava, in terms of her career and rightly so. It’s a really wonderful movie. What was your experience working with her on her vision for this movie? I know there were issues of having to rewrite Dr. King’s speeches without the licensing.

She’s just fearless, so it’s thrilling to be around. She knew how high the bar was. She had every intention of delivering. I can’t think of another person other than Ava who would’ve said, “I’m going to do this. I’m going to get it right and it’s going to be great.” I really mean that, I don’t mean to be hyperbolic. She knew from the very beginning what she was going to do, how she was going to do it, with whom she was going to do it. And so it was like watching a general, very in command and in control. That’s what you want.

The Big Short is the first of a couple movies you did with Adam McKay. I interviewed his casting director, Francine Maisler, for this series a few years ago.

We introduced them!

She talked about his relationship with actors, where there was no real cap on who they could reach for, who would want to do it. Obviously he was a little bit younger in his prestige career, whatever you want to call it, but even in The Big Short, you’ve got a young Jeremy Strong and you’ve got Steve Carell and Christian Bale, this incredible cast. How did you experience what he’s now known as, this singular director of big stars?

There have been a few movies that have attempted to kind of straddle that tonal line, but when we read Big Short, it really felt like the first one. We’d never seen anything like this. There was just this ferocity and also an enormous sense of fun. It contained multitudes, which Adam does. He just thought, “Here are all the actors who should be in it, so let’s go try and get them,” and we did.

It seems to work for him, that strategy.

Because he’s really a joy to be around. You feel smarter for having spent a day with him. You’re off to read about six books, you know more about politics, sports, philanthropic giving, the climate. It’s like living inside an encyclopedia.

His next movie with you, Vice, incited some controversy. I remember Christian Bale thanking Satan for his inspiration when he won the Golden Globe. How do you think about navigating all that, in a movie where you’re talking about living political figures in an incredibly forthright and satirical way? 

Oh, I didn’t question it. Adam was talking about a lot of things in that film; he’s interested in lifting the curtain on things that should really be quite obvious, but seemingly aren’t. So when he goes into sort of, How did Fox News really start and where did Roger Ailes start? Or how did this person vote on all these issues? That’s all information that’s available to everyone. It was right there. I support what we did.

Critically, Vice is the most divisive best-picture nominee on your résumé. Do reviews tend to surprise you or not? Or how do you take them generally?

It kind of depends on my mood. [Laughs.] I read them. I’m interested. I am always interested. If someone has something intelligent to say, I want to learn, I want to know. I mean, I’d be an asshole if I weren’t. Like, “Okay, what did we get right? What did we get wrong? It never occurred to me that X could be interpreted as blah, blah, blah.” It’s super valuable, but that being said, I also think there are colossal misinterpretations of things, and you can’t take it personally. I’m trying to change conversation and nudge, I don’t know, alternative thinking. Not everyone’s going to agree with you.

Based on what I know of Plan B to this point, this had to have been, if not one of the smallest, maybe even the smallest movie you’d made.

For sure, the smallest.

I get it—you read that script and you kind of have to make it. But what were some of the challenges there, given that it was such new territory?

First of all, we learned a lot from the people at Pastel [Productions]. Adele Romanski is a genius. We hadn’t done it before, but I’d worked on super low-budget movies as a kid, $900,000 in New York for those little, you know.

Which wasn’t that far off from this.

No, I know, I know. But it was learning a new skill set. How do you do a micro-budget film? We’ve since done two others and we’ll do more. It’s very hard, and I think it’s a particular skill set. You have to have a ninja sleuth in your line producer, and the text has to be able to support that approach. But that’s what we were going to get, and it felt like, “Okay, let’s figure it out because we have to make this movie. He has to make this movie.” You embrace the circumstances and the conditions that dictate them, and then you go make it.

You were saying earlier that a great function of the Oscars is getting people to see a movie and giving it a long life. For a movie like this, where there are no big stars or anything, what does that kind of trajectory mean to you?

You don’t go and make a $1.25 million movie and think it’s going to go the whole way—you just don’t. But the minute the movie started being viewed, you knew it was very alive and kicking and really connecting with people. So that’s very meaningful along the way. You think, This movie’s going to have a shelf life and people are going to find it and it’s going to be a Valentine for years and years and years and years and years. I think the coolest thing is it really confirmed that you don’t know—you just don’t know. None of us do, which is what partially makes the job fun because, if we all knew, I suppose we’d be out of a job.

Even with the miracle of that Oscar win at the end that people were not expecting, it had already gone so far. Moonlight is, to me, one of the clearest cases of that Oscars trajectory allowing a movie to find its audience.

It felt faith-giving. I don’t always think the right thing happens, but sometimes it does, and there is nobody on the whole planet more deserving than Barry Jenkins. So yeah, that’s the other thing: When you encounter someone like Barry—the talent, it’s next level. It’s not normal. The idea that the success of this movie would create more opportunity for people to see more work from this human is as good as it gets.

Sarah Polley has talked about how she experimented with changing the way a set is run and reengineering the entire moviemaking process. How did you find those conversations? Did you learn from them? What was that give and take like?

It felt like a really collaborative endeavor. She was nervous about directing. She has three little kids and so [Frances McDormand] and I said, “Well, let’s do it the way we need to do it. Let’s do 10-hour days.” What was so enlightening about it is you realize, Oh, one can do this. You can do this properly, and it makes for a better experience, and I believe probably makes for a better film. So we should probably just do this as a rule, or certainly put it on the table. You might have a party of people who aren’t as interested in it, but I don’t know, I think most people would be. It’s protective of family life, it’s protective of sleep, it’s protective of health, it’s protective of creative-thinking time. I mean, it’s got a lot of things in its column. I loved making Women Talking deeply.

The film is made on a scale you might not expect from the source material or log line, which felt like a statement unto itself. 

Two things. One, we knew just cinematically and for the experience of sitting in a theater, you had to get out of the hay loft, you just had to. It also felt really essential to show what a colony looks like and understand the ruralness and the proximity and the network, the kind of constellation of it. And yeah, I don’t think the subject matter is a small subject matter, so I didn’t want to treat it that way. The conversations inside that film and the hope that it engenders and the charge that it makes of, What would it feel like or look like if you could imagine a different future? That feels about as essential a conversation as I can think of. I think standing up to authoritarianism is essentially the issue of our time, and this movie is a narrative inside of that vessel. I wanted to make it as big as we could possibly afford.

Going back to what we touched on earlier. The film’s best-picture nod hardly felt assured by nominations morning. Pieces circulated commenting that men in the Academy weren’t going to go for this, which I suppose wasn’t exactly true in the end, but it didn’t do as well as initially hoped. How did you take the kinds of conversations and the evidently limited amount of attention that some people in the industry were willing to give it?

It upset me. I was really bummed. When you read, “Well, men won’t see this,” you think, Why not? Truly, tell me why not? And if you believe that, then use your platform to say, “Maybe because of the title you’ll be disinclined to see it, but I’m telling you, go see it.” If they’re not doing that then maybe they’re not liking it in the first place, and then I don’t really know what to do. The conversation of and the questions asked by this movie are for everyone. We’re all wrestling with unstable futures. So I find it very strange. Well, on the one hand, I don’t, because we live in a patriarchal fucking cesspit. But the unwillingness to bear witness to violence against women as the epidemic that it is, I find stunning and upsetting and sad-making.

This interview has been edited and condensed.