I feel really lucky to have grown up in L.A. with the parents that I did. Both of them are artists—my dad is a writer and my mother is an editor and a painter—and they showed me a side of the city, perhaps by virtue of the fact that they're relatively anti-social, that was really wonderful and heartening: a lot of hiking, dogs, and surrounded by books and paint. But it's also sort of inevitable that you'll be affected by some of the values in L.A. So I was a 14-year-old with blond highlights, acrylic nails, and a fake self-tan. Yet there's a lot that I learned from that about the inherent contradictions or dichotomies that are at play in all of us as women. It taught me that you can embrace all of the things that you love about being a woman, even those that can be potentially damaging.
My dad got sober when I was 10. He was an alcoholic and a heroin addict, so using and sobriety were things we talked about very openly in our house. There was always a level of openness and trust. I think because I was kind of coming into consciousness as a person at the time, I really benefited from discussions about addiction, about the fact that people are fallible, and that people make mistakes. But it also made me be like, “I'm never gonna do drugs or drink.” Because you interpret things in a very binary way when you're that young.
I smoked weed for the first time visiting my sister at college. My brother and sister were both big stoners. I think they tried to hide it a little bit more, which is funny because my mom was smoking weed that whole time, too. Now, everybody smokes in our house.
I really feel like weed changed my life. I'm a very energetic, hyperactive person. I go at a really fast pace. And my siblings, cousins, and I are all really close—in age and in vibe. But I just remember this marked shift in them after I started smoking, where they were like, “Oh, we can enjoy hanging out with you now.” And it wasn’t because smoking weed was cool, it was because weed allowed me to access a certain level of calm and to start listening a little bit more. I really remember realizing, like, “Oh, conversation is a collaboration.” That probably seems obvious to most people.
Weed also gave me an opportunity to actually enjoy my youth in a way that I don't think I would've otherwise. I was a little bit more of a rule-follower in high school: I was captain of the soccer team, editor of the newspaper, and president of the student body. I didn’t drink. Weed allowed me to have fun without feeling like I was losing control. And I felt like it was very accepted as long as you had your shit together. That ended up being the inspiration for Dude: I wanted to see stoners—particularly female stoners—who were like the women I knew growing up, doing it all.
Most of the representations of teenagers in our media are written by older white men who have no fucking clue what it feels like to be a young woman.
I think that teenagers, and especially young women, are so smart, so sophisticated, and so in touch with what is happening in the world, especially now. They’re aware of their power and are at the forefront of thinking about where we are as a culture and where we should be. They get such a bad fucking rap because most of the time the representations of them in our media are written by older white men who have no fucking clue what it feels like to be a young woman with a group of friends. That's really problematic. If ever something has undermined the possibility and the potential of young women, it's that the representations they saw of themselves were hugely diminished and inaccurate, and then they felt like they had to fit that mold as opposed to being as badass as they were.
One of the beautiful things about social media, amidst all the potential downsides, is the way young people are seeing themselves. It’s created this potential for them to put out to the world their own images of themselves as opposed to being defined by a group of old white people in an office somewhere. And that’s a huge shift.
I went to a wonderful, hippie school called Crossroads, so growing up, I literally never had given it a second thought that as a woman I shouldn't be the first person to speak in any class or that I shouldn’t be the leader of every club at school. I grew up with all these boys whose moms were uber-feminists, so everyone was like, “Women are worshipped.” Until I went to school on the East Coast with all these dudes that had gone to boarding schools and been told their whole lives that they were the leaders of the free world, it had never even occurred to me that they would look at me differently or that I was occupying a space as a woman that they felt I shouldn't.
One of the similarities between Dude and Ocean’s Eight is that you have a group of women loving and supporting each other, while unapologetically living their own lives. There's this old John Mulaney joke that people keep bringing up where he's like, “You could never make Ocean’s 11 with all women 'cause they'd be like, ‘Oh Nancy's such a bitch and like, can you believe what's she's wearing?’” Like they'd never be able to pull off the heist. Somebody brought it up with me recently and I said, “You know, I don't think he would make that joke now.” Because I think our culture has changed and he's a seemingly pretty enlightened dude. But I also think that that joke is representative of this bullshit fallacy that exists and that has been perpetuated not only by language, but representation in media: that groups of women can't do things together.
I didn't set out to be a screenwriter. I thought I was going be president. And then I got to Yale and I was like, “Oh, no. That kid's gonna be president. I'm gonna go get high.” But I was really fortunate to take a class my first semester: “Hemingway, Fitzgerald, Faulkner.” I had read Absalom, Absalom and my father’s mentor was Robert Penn Warren, but I hadn't really dug in. And then I read The Sound and the Fury and I just said, “This is it. This is my dude, this is what I wanna do. I want to study this guy and I want to adapt his work because it's so cinematic.” The way he uses montage is the way montage is used in film. I feel like Faulkner’s work is something that explains and deals with race, the South, and America in ways that nobody else has really done.
I became single-minded—obsessed, really—and I took every class that was Faulkner-related. I tried to read all the history he had read that made up the work that he made. I did Faulkner in film, and Faulkner in adaptation and I ended up doing my Bachelors and my Masters simultaneously because I just got so deep into it. And I was in Mississippi doing research on my thesis between my junior and senior year when I met the executor of the Faulkner literary estate at the Yoknapatawpha Conference. He had been a fan of Deadwood so we got together with my dad and after of series of conversations got the rights to a portion of Faulkner's library and HBO was like, “Yeah, cool. We'll develop this.”
So I graduated from college and I drove down to Mississippi and started adapting Light in August, which was my dream in life. And I was doing it as my first job out of college and it was psychotic. I was sitting in Faulkner's backyard writing, feeling like this is the most magical thing that's ever happened to me. I was like, “Amazing! They're definitely gonna do this and this is gonna be great and this is gonna get made.”
The reality of being a writer is that 99% of the stuff you do never sees the light of day.
But that didn’t happen. The reality of being a writer is that 99% of the stuff you do never sees the light of day. Growing up, I was privy to the machinations of the industry and learned early on that most shit doesn't happen. You learn to just feel really lucky to be getting paid to write, period, and to keep your expectations basically non-existent. Everything moves glacially. I feel like I end up giving the same little spiel to my younger friends who are coming up in the industry, where I'm like, “Okay. You're gonna have meetings for two years and at the end of every meeting, someone's gonna say, ‘We love you! You're great! Let's do something together.’ And nothing will ever happen.”
You just have to be okay with knowing that eventually, one person's going to take a chance on you and pay you to write something. I started writing Dude because I realized nobody had ever read any of my screenplays, because my samples were all Faulkner and nobody wants to read Faulkner. So I wrote Dude and people were like, “Oh, oh, oh. We get it. We get who you are now.”
And that’s how I was fortunate enough to meet with one of the most amazing people in the industry—a brilliant, funny, firecracker of a woman whom I idolize: Amy Pascal. And she gave me a chance. She was the one who hired me to do an adaptation of Little Women. There's this weird catch-22 where nobody will give you a job until somebody's given you a job, and she gave me that opportunity.
I'm a really firm believer in sending the letter and reaching out.
It goes to show you how important it is, especially in this industry, to hold the door open for other women and say, “The tent is big, come in.” It's such an important process and one that I feel really fortunate to be able to start engaging in, which is to be working with younger female-identifying writers.
I can’t pretend that it wasn't helpful to have my dad work in this industry. The reality is that it is about connections, but that's not to say that you need a blood connection. You have to reach out to people. Because nobody will vouch for you or believe in you unless you come with a co-sign.
I'm a really firm believer in sending the letter and reaching out. Most of the jobs that I feel like I've gotten is because I wrote an e-mail where I was like, “I really care about this. Can I be a part of it?” You need to be unafraid of saying what you want out loud and asking for help. And when you get in the door, what you do with that is up to you. But it's really helpful to have somebody be able to make a connection for you. In other industries, there's a prescribed course of action: you're a junior associate for two years, and then you do this. In our industry, there's not.
The thing I always say to younger writers is, “You're really fucking smart. You're really talented. Your shit is better than 99% of the shit out there, and I can say that just talking to you for five minutes because most of the stuff out there is such trash. But you have to have the confidence to know that you matter, your story matters, and that people wanna hear from you.” Because confidence is what people ultimately respond to. They're like, “Oh, thank god. You think you can do this. Please.”
I’m currently working on an adaptation of a graphic novel called Queen & Country. It’s about a female MI6 agent, like a female James Bond. I’m also working on a show about Clare Boothe Luce with my friend Ariel Doctoroff. Clare was a badass renaissance woman of the 20th Century. She wrote the play The Women, was an editor at Vanity Fair, a congresswoman representing Connecticut, and ambassador to Italy, among countless other things. She was married to Henry Luce but also had all these wild affairs. She claims to have coined the phrase “No good deed goes unpunished.” But most people have no clue who she is. Luce was also at the forefront of medicinal acid—dropping acid under doctor supervision. The whole show is an acid trip—she drops acid at the beginning and it’s eight hours through her life.
And then just a bunch of other projects about excellent women.
Olivia Milch photographed by Meredith Jenks at her home in Brooklyn. This conversation has been edited and condensed for clarity.