Natalie Portman and Greta Gerwig have played best friends in two movies that could not have been more different: 2011’s No Strings Attached and 2016’s Jackie. And though their careers have followed different paths since then, it’s clear that their warm friendship wasn’t just for the cameras when they sign on for this Reunited Zoom chat.

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Their 45-minute conversation is full of laughter, so much so that sometimes the conversation gets sidelined as they reminisce about those projects together. But they also dig deep into the fascinating parallels of their careers.

Portman directed the 2015 movie A Tale of Love and Darkness, and she’s also become a full-fledged producer, cofounding the production company MountainA in 2021. The Oscar-winning actor produced her latest film, May December, in which she delivers a captivating performance as an actor studying a controversial subject (Julianne Moore) for her next project.

Gerwig has gone from an indie-darling actor to an incredibly successful writer-director. After writing and directing Lady Bird and Little Women (both of which earned best-picture Oscar nominations), Gerwig cowrote and directed the highest-grossing film of 2023, Barbie, now an awards season front-runner.

Their paths have crossed in other unexpected instances too, like when Portman had Gerwig’s name embroidered on part of her 2020 Oscars outfit as a nod to the female directors who were snubbed; Gerwig acknowledges that they remain connected in a “cosmic way.” Here, they reunite to reveal the sage advice they’ve shared over the years, the funny things they’ve discovered about each other (like unexpected cat allergies), and how they each finally committed to pursuing their behind-the-camera passions.

Vanity Fair: What do you remember about the first time you met?

Greta Gerwig: It was on No Strings Attached. I do definitely remember, for whatever reason, the person who was doing my makeup just put a lot of makeup on me, like a lot all the time. And I remember looking at you and being like, She looks wonderful. I don’t know that I need this much makeup right now, but…

Natalie Portman: I feel like we were very upset about our footwear, both of us. They kept putting me in flat sneakers and Greta in clogs that were high. I was already looking like I was from Lord of the Rings.

Gerwig: In the hospital [scene], it was a walk-and-talk and they couldn’t get us in the frame. And I was like, That’s because I’m wearing five-inch clogs for some reason. And she’s wearing running shoes. We look nuts. It was great. It was fun and ludicrous. And you had just done Black Swan.

Portman: I was eating again. I was like, Food!

Gerwig: I remember you in the trailer too. You always knew when it was meal time.

Portman: That’s just kind of a constant. I’m still like that. Always have been.

Gerwig: You’d gone from something so intense and then it was this sort of silly thing to do.

Natalie, was that intentional at the time, or was it just coincidence?

Portman: It was coincidence. There’s very little in my life that’s intentional. I wish I could say, “Yes, I like to balance my career,” but it’s just stuff happens or it doesn’t.

Greta, how would you describe where you were in your career at that time?

Gerwig: I was kind of in between. I had done a bunch of really deeply independent movies and I’d written on those, but they were also improvised. I also had this desire to write and then I was acting. I think it was a moment of transition, but I felt so lucky to be there. I definitely remember that was a time when I’d go to meetings and people would be with executives, and they’d look at me and they’d say, “Are you funny?”

Portman: It just reminded me of when you were talking about acting and how to say lines and stuff. I remember you said something to me on the set of Jackie that I still think about all the time in acting, where you’re like, “Sometimes I just forget that you’re just supposed to say it, like mean what you’re saying.” [Laughs] It’s the most basic thing and it’s like, if you can just focus on that, it’s amazingly helpful. I think about it all the time, and it was so true.

Gerwig: That’s so funny, though, because it’s such a weird thing to say to you, because that’s such a constructed performance with so many layers to think about. And I was like, “I just really try to mean it.” It was like when it is constructed, you forget that sometimes you’re just supposed to believe what you’re saying to the person you’re saying it to. This is such an odd thing, but I love Gene Hackman as an actor and I believe everything he says. I just believe it. He’s in a car and I believe he’s in the car.

Jackie was five years after No Strings Attached. Were you in touch between those two projects?

Gerwig: Yeah, you were in New York for a while. This is weird to say, but I feel like even when time passes, I still always feel close to you in a sort of cosmic way. I feel like there’s going to be a point when we’re in our 50s, where we’ll be in the same place and it’ll be like, Ah, this was always what it was supposed to be. But it’s like I felt like we stayed in touch, and then I was just always so thrilled when anybody ever was like, “They’d like you to do a secondary quote for Natalie.” And I was just like, “Fabulous. I can’t wait.”

Portman: Same. Same. [Laughs] I also discovered my cat allergy at your apartment. Do you remember that very embarrassing dinner party?

Gerwig: I felt so bad because I think in retrospect we realized you were pregnant, which we didn’t know.

Portman: I was pregnant, and I had never had a cat allergy before. And then all of a sudden during this dinner, I embarrassingly couldn’t stop sneezing. It was like 1,000 sneezes.

Gerwig: We had these two cats, Paw Newman and Diane Kitten, and I was like, No, my cats are killing Natalie.

Portman: It was a discovery, and I’ve had it ever since. It was a pregnancy-related allergy that stayed.

Did the two of you learn anything from each other when it comes to acting at that time of your career?

Gerwig: You had [Portman’s son] Aleph at home, and it was the first time I had seen—because I stayed with you for a little while while we were making Jackie, and I was also seeing the role required so much commitment, I saw you kind of able to shift in and out of it, being there and then being with them. I felt like that was kind of just instructive to watch someone go through that. And for me, it was watching her find the humanity through all the technical things on top of it. You can get mired in that. It almost felt like a statue cracking or something—it was so many layers of performance. And I was wearing this enormous wig the whole time, and I was sort of like, Just try to look normal. I was always sitting behind you while there was something happening and you were doing something amazing, and I was like, Just keep your face as neutral as possible. That was that sort of heightened-ness, but then finding the ground—I feel like May December is sort of similar in a way. Do you feel that way?

Portman: I feel like it’s what I’m drawn to—heightened expression, yeah. But I feel like getting to spend time with you on both those sets, I’ve never met anyone—it’s hard to say with you here— who’s so smart, and interesting, and cool, and not intimidating at all. Just having the openness and loving and putting-you-at-ease sense at the same time as having the most interesting story, and listening to the coolest music, and knowing all the interesting stuff, but not in an intimidating way at all. And it was so clear that you were going to create magic. Because I feel like you directed Lady Bird soon after that.

Gerwig: I think I had the script, actually.

Portman: I remember you talking about that you were going to direct your first film, and that you had just worked with Rebecca Miller and you had just worked with Mia Hansen-Løve, and that you were geared up for it. And I was like, Oh, this is going to be great. And then I remember seeing it at Telluride and I was like, Oh, my God, this is just the greatest. It had your spirit and generosity. That’s the thing, your films are so good and they’re so generous of spirit. It’s a joyful experience.

Gerwig: It’s like that funny moment when you have a script—it’s like your secret. I remember reading about Martin McDonagh—when he wrote Beauty Queen of Leenane, he wrote it when he was on the dole in Ireland. He said he went to the pub and he’d written it and he thought it was good. And he looked around and he saw all these people with their girlfriends, and he’s like, They have girlfriends, but I have The Beauty Queen. It was this feeling inside, and it is that sort of—you’re like, I have a secret world now. And it’s the best feeling.

Greta, you were just at the Palm Springs gala and you said, “It took me a long time to say out loud that I wanted to be a director.” When was that moment that you realized you did want to say that out loud?

Gerwig: For a while it didn’t occur to me, in a way. For a while it didn’t occur to me to write, because when I went to college, I loved playwrights, but I didn’t know very many lady playwrights. I just knew Wendy Wasserstein, but all of the other playwrights I worshipped were men. And I remember actively thinking, like, Oh, it’s too bad I’m not a man. I can’t really do it. But it wasn’t sad, it was just like, That’s just not open to me. And then I had a great playwriting teacher, Ellen McLaughlin, who’s an actor and a writer, and she gave me a stack of plays written by women. And it was like, You’re wrong. Look at all this. Look at Caryl Churchill. What are you talking about?

So then I started writing, but I still didn’t have a sense of directing until I was probably in my late 20s. I mean, I’m not pleased with these thoughts. It’s just what I felt. And then I think between working with women who directed and thinking about it, it was so obvious that that’s what I wanted to do, that by the time I said it, it was like, You wanted to do this the whole time, and you kind of put whatever mental blocks in front of yourself so you couldn’t.

I think I finally said it in an exercise class. There was an exercise class in New York, and it was taught by a woman named Patricia Moreno, who was wonderful. And she would make you do jumping jacks and then scream what you wanted most loud. And I, without even thinking about it, screamed, “I want to be a director!” It was really wonderful. It was mostly women, and people were just screaming things they wanted, and it was very beautiful. Tragically, she’s since passed away, and I saw it in The New York Times and I couldn’t believe it. And I never told her, but that was true.

Natalie, did you have a moment when you realized you wanted to direct and produce?

Portman: I feel like I similarly had these weird biases against it. I think kind of coming of age in the ’90s, I remember reading things—like when Barbra Streisand would direct, I would read reviews that would be commenting on how she lit herself. They would talk about her vanity, and then you’d see the men actors who became directors, like Kevin Costner and Mel Gibson, winning Oscars. And then it was the one woman I felt…was kind of an actor who became a director [who] was really given a really hard time about it, even though of course she was nominated for Oscars and things, but was definitely criticized in a way that I didn’t see the men criticized.

But for me, that made me embarrassed about it. Particularly, to act in something that I’d like to direct myself as an actor felt like, Oh, I can’t do that. That’s vain. Then John Calley, who was one of the producers of Closer who became a really good friend of mine, really constantly—every time we would talk—was like, “When are you directing? When are you directing?” And that was really, really important to me. Eventually, I did it. I didn’t do it again for a long time. Greta’s inspiring of how to keep making the magic while also having a family and everything.

Did playing an actor in May December change your perspective on your profession at all?

Portman: Yeah. I think that the layers of performance that we were looking at, of how we perform all the time, and of course an actress epitomizes that. But even the first scene of Elizabeth walking into the barbecue is a performance of, I’m just a regular person who can hang at a suburban barbecue. It made me conscious of that in my own life—when am I performing? I mean, obviously I think about it all the time and it’s questions I consider all the time and how much that affects identity.

It definitely made me look into it more deeply. And then also of whether art can be amoral, I think we’re constantly talking about, Oh, I don’t judge my characters. I’m just interested in portraying the human heart, or whatever. But when you’re portraying a crime, is it possible to depict a crime without somehow endorsing it, or exploiting it, or amplifying it in some way?

Greta, did the massive success of Barbie shift your own perspectives on Hollywood in any way?

Gerwig: It changed my perspective. When we were in the lead-up of putting it together and getting the greenlight, and outside of even how wild and anarchic and bananas the script was—which it was—the people who believed in it and fought for it put themselves extremely on the line to get it made. I later found out that they have to do all these numbers, that they project things to decide whether or not this is a foolhardy venture. And all the numbers said, “You never should do this, or if you do do this, do this in a totally different way.” And [the Warner Bros. and MGM executives] really put themselves way out there, to the point where I know that there were numbers that were invented in order to support this being made—they didn’t exist. So actually, they went and they were like, “Get those numbers higher. We’ve got to figure this out.” Even up until six weeks before it was released, it wasn’t something that everyone thought, Well, that’s a three-pointer. Everything about it was uncertain. And I think one thing was, I was just incredibly moved every step of the way by how people rallied around it, put themselves on the line for it, put their reputations on the line for it to go for it.

Portman: I feel like you guys set a precedent that is now going to open doors for so many kinds of risky storytelling. People obviously talk about female directors and female-forward, but I think the bigger thing is just risky storytelling on a large scale. I couldn’t believe when I sat with my daughter in a packed opening night movie theater with this crowd laughing, and screaming, and dancing, and applauding, and then we left, and my six-year-old goes, “Mommy, what’s the patriarchy? Can you explain it to me?” And I was like, This is the best thing that’s ever happened! Mass entertainment that’s about something and is so wild and nothing you’ve ever seen. It’s just so masterful, and no one else could have done it.

In your careers, was there ever a fork-in-the-road moment where it could have gone in a different direction if you’d chosen differently?

Gerwig: It’s a million little things. I don’t think it’s one thing. I think one thing I’m grateful for in retrospect is that I never sort of shut down sides of myself. The thing I’m thinking of is, actually I did a pilot for a sitcom, which didn’t end up happening, but I loved making it and it was so fun, and it was network television. It was writing to the commercial break, and I worked a little bit with the writers, and there was something about it where I was like, This is a really exacting form. It’s kind of amazing. I remember they told me they tested it in Vegas, and they said they give people knobs and you turn it right if you enjoy what’s on the screen and you turn it left when you don’t. Apparently, every time I came on the screen, they just all were like, No, no, get her off my television. [Laughs] But I just loved the experience. I remember someone sent me something that was like, “Why is she doing this?” And I just thought, I’m not an object. I feel grateful that I just have been able to follow interests that seem on the surface to be incongruous with some preexisting identity.

Portman: Similar to what Greta said, it’s a lot of little moments. I’ve been working 30 years now, which is kind of insane, so there’ve been a lot of moments where I’ve done things. I guess the truth is that the thing you learn over that amount of time is, no decision is that important.

Gerwig: Actually, before No Strings Attached came out, I was at your house. You were in New York, you were extremely pregnant, and I was stressing about whether or not to do something. And you said, “There’s lots of reasons to do something. There’s not a perfect reason. It doesn’t have to be pristine if there’s something in it.” And I was like, “Right.” Sometimes you do something and you don’t know exactly why, but there’s something that’s pulling you toward it.

Portman: Mike Nichols always said that saying no was always the most important part of your identity, what you say no to, and that was really helpful to me because there’s also the converse of what you’re saying, of that there’s many things that can draw you to something. There’s also—something can be really good, and everyone’s like, “You’re crazy to not do this.” And sometimes you’re just like, It’s not the right time in my life, or it’s not drawing me in, even though everyone else thinks it’s amazing. And you have to be true to that.

Gerwig: When I look at directing, I love careers that span decades and have different moments and things that work and things that don’t. But then even the things that don’t, you kind of see how they work their way into something else. I guess as a director, I’m like, Just keep making them. Just keep doing it.