From Hollywood to Chicago, Katherine O’Brien is helping aspiring screenwriters

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Katherine O’Brien

Katherine O’Brien is a brilliant, comedic, down-to-earth individual. For fifteen-plus years, she’s thrived in Hollywood and throughout the international marketplace as a screenwriter, filmmaker, and story consultant.

As a faculty member at Second City’s Harold Ramis Film School and a teacher at DePaul University and Columbia College Chicago, Katherine O’Brien has mentored and supported young filmmakers throughout Chicago. I am happy to know Katherine and love sharing her story.

GROWING UP

REBECCA MARTIN: Where did you grow up?

KATHERINE O’BRIEN: I grew up in the Chicago suburbs, in Glenview, and I always loved performing, always involved in performance activities in school and outside of school.

MARTIN: So were you acting?

O’BRIEN: I was acting, yes. My love for theater and performance led me to work extracurricularly with my high school’s improv group in sketch comedy. When I was doing that during my senior year in high school when I was trying to figure out what I was going to do in terms of college, I was planning on going into politics or law, and I was like, “Performing, comedy, this is what I really love. … This is what I’m passionate about. This is what gets me excited, waking up in the morning.”

In high school when I was trying to figure out what I was going to do in terms of college, I was planning on going into politics or law, and I was like, “Performing, comedy, this is what I really love. … This is what I’m passionate about. This is what gets me excited, waking up in the morning.”

MARTIN: What drew you into comedy?

O’BRIEN: I’ve always been kind of a goofball. I wasn’t exactly the class clown per se, but I was just always goofy, just enjoyed being silly.

MARTIN: That’s a gift by the way, making people laugh.

O’BRIEN: That’s what I really like, I found it really validating, when I could cheer people up. You know, when I could lighten a mood. I would entertain my family and friends with my goofball antics and impressions of them.

MARTIN: That’s great.

O’BRIEN: Which led me to want to do more of it, and I had fun playing onstage with friends who were the same way. You know when you find your tribe and your community it’s just really…

MARTIN: Find your people.

O’BRIEN: Yes, find your people. Your people that just get you, and love you, as weird as you are. It’s wonderful.

MARTIN: Exactly.

O’BRIEN: So I just wanted more of it. Then, senior year, one of my theater friends was like, you should apply to film school. I was like, I know nothing about film, other than that I enjoy watching movies.

MARTIN: Same here with me, that my thing, watching movies.

O’BRIEN: Yeah, I think a lot of film schools attract movie fanatics, that are like, “I love this culture, I love this world, and I want more of it.” It draws creators in that way. So that’s what drew me in. Incidentally, what got me to apply was a buddy of mine leaning over to me in English class and saying, “Dude, there are no chicks in movies; the film industry needs more women.” And I was like, what?! My social justice alarms went off, “I will be that woman.” So that’s why I applied, and when I got there we had a pretty balanced group of male and female content creators in my screenwriting program, which was nice.

I think a lot of film schools attract movie fanatics, that are like, “I love this culture, I love this world, and I want more of it.” It draws creators in that way.

MARTIN: Any women mentor or inspire you in your craft?

O’BRIEN: There were very few female professors. I had three, and one was not actually my professor. She was my TA for critical studies.

MARTIN: Oh no.

O’BRIEN: It was really like, “How do I do this, how do I navigate this?” And one of my directing professors was the incomparable Nina Foch, a legendary actress from the studio days. She really had a long career. So she was my directing instructor and was very old school. And I was the only woman in the class of mostly graduates, for directing. I was fortunate to get in as an undergrad. And I was the only woman in the class.

And I would come in every day in a track jacket and wet shower hair. And she pulled me aside one day and she was like, “You need to meet me in the ladies’ room right now.” So I’m like “Okay…” and we went, And she was like, “Listen, if you don’t take yourself seriously then no one else will take you seriously in this industry. As a woman you have to try harder. You need to come to class dressed to impress. I want your hair done, I want you in makeup, and I don’t want you in these pajamas.” And I’m like, “It’s a track jacket, it’s vintage. She was like, “If you bought it in a thrift store, I don’t want it in my class.”

MARTIN: So for the guys, no problem, they can come in however they want. That doesn’t seem right, although I understand what she was saying.

O’BRIEN: Right, so as a young twentysomething, it really pissed me off. And as I’ve gotten older I’ve understood where she was coming from. She was just trying to convey how hard it is to be taken seriously. Not only as a woman, but a young woman in the film industry. And that would follow me throughout my career. And I came up against that time and time again.

It was only with the #MeToo movement that I found the courage to talk about that, and really face what those challenges were like for me, and for other women I came up with in the industry at that time. I think that one of the most profound repercussions of the #MeToo movement is that there’s been this super visible call to action to support women, femme-identifying content creators in more substantial ways. Which is awesome. But I think Nina’s advice to me back then is nevertheless relevant today—if you don’t take yourself seriously, no one else will. I’ve internalized it now as more like—believe in yourself. Take the risk. Try. Do. Don’t wait to feel “ready” or “prepared”—Amy Poehler was just mentioned in an interview talking about this very thing, as advice to female directors blazing their trails.

SCHOOL TO INDUSTRY

O’BRIEN: When I was at USC, I started interning my freshman year, and I got a really great internship because of a family friend connection. At the internship, I was treated very well, I didn’t have to do copies, I didn’t go fetch coffee, I was 100 percent there to learn. Which was amazing.

MARTIN: What was the internship?

O’BRIEN: The internship was a major production company, and one of the senior execs was my boss. He and his assistant mentored me, give me all the best scripts to read, and then gave me some bad ones so I could learn the difference. And I spent every day there just reading, and talking to them about the scripts that I read. So they helped me cultivate my taste, and then it was easy for me to contribute relevantly, creatively. I was helping them get through piles and piles of scripts, and learning how to evaluate writing samples and getting to know the world of story development.

They gave me this incredible education that’s hard to get in a classroom because it’s real-time, professional world experience. That’s part of what actually drew me to teaching in film schools—I wanted to bring that real world experience to my classrooms in a way that I felt was not part of the curriculum when I was in film school. So my first internship experience was pretty amazing, and that exec became a mentor to me throughout my career, and helped me get internship opportunities because his assistant connected me to other assistants.

That’s part of what actually drew me to teaching in film schools—I wanted to bring that real world experience to my classrooms in a way that I felt was not part of the curriculum when I was in film school.

So those assistants were like, “Well if you think she’s great, I’ll hire her.” So I got my next internship through the assistant network. l landed at a desk supporting a junior executive who didn’t have his own assistant yet. So I basically worked as his assistant, and he was like, “Anytime you want to come in to a meeting, let’s go.” So I got to join him, meeting writers and directors. I went to screenings. I gave notes on projects that they were working on. I helped assemble their production binders.

I got to go to set and PA in the art department, and as a PA for the producers. And that was all during my first three years film school, so I was like seventeen, twenty years old, and already had this major studio and major production company experience working in story development at a very high level, in a very hands-on way. It was amazing. And it’s definitely what helped me launch my career in story analysis and script consulting—where I was basically just working with writers, filmmakers, producers, execs, helping them fine-tune their scripts.

MARTIN: When did you decide to pursue working with scripts?

O’BRIEN: I didn’t realize I had a skill for it until I had been working as an assistant after graduation for a full year. And I realized that my bosses relied on me to give strong story notes, to edit the notes, and were relying on my writing skills in my screenwriting background to help shape projects. And I was able to build a reputation in the industry, within my network, for being able to do that well.

PROCESS

MARTIN: How does the screenwriting process go?

O’BRIEN: The story writing process is that the script is really just the blueprint, the template of the story, and there are different schools of thought here: Some people view a screenplay as a form of literature and they will analyze the text in a literary way, and really take it seriously in that vein. There are others who are like, “No, this is just a production document. This is something we want all of our department heads to converge on, and then break apart and go interpret for their specific crafts and arts.”

There are different schools of thought here: Some people view a screenplay as a form of literature and they will analyze the text in a literary way, and really take it seriously in that vein. There are others who are like, “No, this is just a production document.”

For me, I am very practical and understand that this script has to be produce-able. But I love it when a script is written beautifully, like has these cinematic, literary elements. Because the best screenwriting is really like poetry. And that makes me filled with joy when I read a script like that.

The best screenwriting is really like poetry. And that makes me filled with joy when I read a script like that.

MARTIN: That probably makes you more interactive with the film when you see that deep sense of thought.

O’BRIEN: Totally. When there is a script written by a writer who can do that, I think it does influence how the film is made.

MARTIN: Are there any screenwriters that you really connect to in that way?

O’BRIEN: Many. But working on a script by Eric Roth—who wrote “Forrest Gump,” “The Insider,” “Munich,” “The Curious Case of Benjamin Button,” and “A Star is Born”—really taught me a lot about this connection between the literary and the cinematic.

Working on a script by Eric Roth—who wrote “Forrest Gump,” “The Insider,” “Munich,” “The Curious Case of Benjamin Button,” and “A Star is Born”—really taught me a lot about this connection between the literary and the cinematic.

I got the chance to work on “The Good Shepherd” during the preproduction. One of my jobs was to do draft comparisons for every draft that Eric was writing. So we had the last draft he wrote, and the most recent draft that he wrote, and I would go line for line and compare what changed between the two. I think someone would type everything up for him on a typewriter or something. It wasn’t written in screenwriting software.

So we had to figure out what was changing, and manually highlight the changes. Doing that really gave me an opportunity to closely read his work, and I learned so much about the craft of screenwriting and storytelling from that experience. The literary-cinematic was in seeing how he would use characters interacting with specific objectives as metaphors, or having his characters play a game in a scene. They’re tricks I’ve adopted into my own writing as a way to help show the inner world of a character in a way that translates to screen. To this day that is the first script that comes to mind as “Wow, that was an incredible script.”

MARTIN: I love that. What I love about filmmaking is the collaboration, people coming together, believing in the story and vision, and seeing it materialize.

FEMALE SCRIPTWRITER

MARTIN: What are your thoughts of being a woman in the screenwriting business?

O’BRIEN: So I think that’s really interesting … where we’re at in this moment in time, which is an exciting time for female screenwriters, for all underrepresented screenwriters … there’s a demand for that perspective in the writing and that point of view in the telling of stories. Even though there is no monolithic gender- or race- or sexually-oriented perspective. There is nevertheless a demand for working with whatever those underrepresented perspectives might be, which is exciting and empowering us right now. So I’m loving that, because I’m getting new opportunities in my work, in part because I’m a female screenwriter who can tell stories in specific genres, in comedy, in the drama and thriller space, and in combining the genres as well. I love mash-ups.

MARTIN: Yeah, you have a vast amount of experience; you’ve worked with so many people as well.

O’BRIEN: The challenge though, earlier in my career, for example—a lot of people when I was first coming out as a writer, I had this great film school experience, I had this great story development experience working for studios and production companies. Working with the writers, directors, producers, actors… working with all the agents, the managers… the different personalities that have to come together to mediate, get the script together, give notes on writing it. And everyone has different notes, and they all have to somehow be unified, visually, like we were talking about. All of that experience was valuable to producers as I was breaking out on my own as a screenwriter. They were like, “We want to work with you because you get it.” I didn’t have an ego about notes, I understood how everything had to come together. I’m a collaborator. And they were like, “We understand you can be that team player,” which was fantastic for me.

The flip side is that I felt that how I appeared in a room mattered. Maybe it was Nina. Maybe it was the industry expectations or just living in LA. But I had amazing female mentors at this time, who were my bosses, execs, and colleagues, who supported me with everything from advice on how to be assertive as a writer in meetings to the best place to go get my eyebrows done. So yes, looking the part, but also how to play the part in a strongly voiced, empowered feminist way. Their sisterhood was incredible.

I really struggled with feeling like I had to be a certain way, play a role, look a part… it’s a part of the business world whether we want to admit it to ourselves or not, and there are ways to harness that power and ways we may feel beholden to it… and that feeling of being beholden to it really frustrated me.

But I really struggled with feeling like I had to be a certain way, play a role, look a part… it’s a part of the business world whether we want to admit it to ourselves or not, and there are ways to harness that power and ways we may feel beholden to it… and that feeling of being beholden to it really frustrated me. So I’d go into a room and I had a pink water bottle and a pink laptop case, which I still have, but the idea was like I’m projecting this image of femininity, and I’m writing material that is fluffy girl stuff; I have to convince people that I am an expert in that world, even though I didn’t really feel like I was “one of those girls.”

MARTIN: So were they drawn to the manufactured you? The you they wanted you to be? Or the real you?

O’BRIEN: So my manager at the time, who is still one of my dearest friends, Shannon Riggs, she is an amazing producer. She was like, “I think people are drawn to you because of your kindness and your willingness to do anything to make it happen.” So I guess that would be the real me. That’s genuinely how I am. But I felt this pressure nevertheless to fit a certain feminine aesthetic.

A lot of it reminded me of performance days. Who are you going to be cast as? What’s your type? And whether I was all that consciously aware of it or not at the time, I think I was always kind of trying to figure out how my writer voice fit my “type”—how I came across in the room, what kind of woman I was, what kind of female perspective did I have. I fit even though no one explicitly said that to me. Not micro-aggressive comments, just sort of the subtle comments that were made. Like when I wrote a script that was a male-driven comedy, a lot of the compliments I received were like “Wow, I can’t believe this wasn’t written by a dude.”

When I wrote a script that was a male-driven comedy, a lot of the compliments I received were like “Wow, I can’t believe this wasn’t written by a dude.”

And that’s the thing, we’re still in this space in the industry, where A-list male writers like Judd Apatow or “Game of Thrones”‘ David Benioff can be both criticized and applauded of their treatment of female characters, because they are men. And so when they do it well, they’re like, “That’s so great you can write a female character that well.” And if they mess it up it’s like, “You failed because you’re a man.” Because anyone who reaches that level of fame also reaches that level of scrutiny based on their identity. And I think with identity politics, while we’re in an exciting time, creating more opportunities, they are nevertheless pervasive. Liberating in some ways, but limiting in others.

FEMINIST STORYTELLING

Ten years ago, the perception of feminist storytelling was like women acting like men. Even if you go back to “I Love Lucy,” much of the comedy that the show gets is when Lucy and Ethel puts on the pants.

O’BRIEN: Something I was recently exploring, in my reflection of my creative work that I had to do for teaching, was that ten years ago the perception of feminist storytelling was like women acting like men, still. Even if you go back to “I Love Lucy,” much of the comedy that the show gets is when Lucy and Ethel puts on the pants, or put on a hat, you know? So from “I Love Lucy” to the 2000s, we were in this era. I mean you can look at Goldie Hawn’s movies in the ’70s and ’80s, it was women acting like men. Can they be raunchy? Can they be dirty? Sexually and physically. Can they be tough? Can we take, you know, “Legally Blonde,” she’s too pink, she’s not serious enough for Harvard Law. The success in these movies were very much rooted in women acting like men. And now I think we’re at a place where we can push beyond that and innovate.

My current project, my current approach in feminist storytelling, is that I don’t want to write stories with female protagonists that are acting like men. I want real women and I want to explore what that is, in all of its differentness. Because I can’t sit in the writer’s room and give you the female perspective. I can give a female perspective for this woman raised in the Chicago suburbs, spent some time in LA, and now is back in Chicago and is a mom, and has two sons, or whatever else.

There are all these different facets of our lives, and I think they are there to engage with these dialogues. And it’s happened a lot to my writer and director friends who are not white, being like, give us the Black perspective. Give us the Latinx perspective. It’s like, dude, it’s really a heavy burden placed on us in this way. Whereas, yes, [they’re] giving more visibility to these voices, and yet we still have white cis men who can just write anything, be anything, do anything.

It’s really a heavy burden placed on us in this way. Whereas, yes, [they’re] giving more visibility to these voices, and yet we still have white cis men who can just write anything, be anything, do anything.

COLLABORATE

MARTIN: Do you have any women that you collaborate with on stories?

O’BRIEN: I do, I especially love working with my friends and colleagues here in Chicago at Second City. I try whenever I can to create opportunities where I can bring in my former students, who I think are so incredibly talented, into the mix of any projects. I love working with my female producing partners. On one, I’m working with a fellow mom of little kids. It’s great to have creative partners that empathically and intuitively understand everything you’re juggling.

MARTIN: That’s great, you have those relationships.

O’BRIEN: Yeah, and that’s what I just love about being here.

MARTIN: Yeah, Chicago is very different than LA. What do you like about being in Chicago?

O’BRIEN: I love the independent collaborative spirit. And how we are uniquely poised as a city, as an arts community, to continually elevate the voices of underrepresented populations.

I love the independent collaborative spirit [of Chicago]. And how we are uniquely poised as a city, as an arts community, to continually elevate the voices of underrepresented populations.

FOR THE YOUNG FEMALE FILMMAKER

MARTIN: What kind of advice would you give young women starting out in the industry?

O’BRIEN: Find your crew, find your squad. Because together we can. There’s all that cultural gossip that I felt when I first got out of film school that women were not in the business to help each other out. And fortunately that was not my experience. The women that I met were all about, “I got here because someone helped me, I’m going to pull you up with me.” And that’s also the way I want to be. I mean, I teach and I mentor, to be that woman that helps other women get into the business, to get their foothold in to the business. Find their footing and nurture them. Help them to succeed on their terms, because I think that success is not necessarily about achieving fame, fortune, recognition even; it’s about finding a creative, fulfilling way to keep the party going.

I think that success is not necessarily about achieving fame, fortune, recognition even; it’s about finding a creative, fulfilling way to keep the party going.

MARTIN: Anything you’d like to add?

O’BRIEN: Something I feel that is really important about Chicago, and the female content creator experience, coming back to that, I think Chicago is a community poised to elevate the voices of underrepresented populations for a few reasons. The improv comedy community here is phenomenal, and intrinsic to that community is a spirit of collaboration, and helping each other out. You know we do this because we can; what a privilege, what a joy, and that the keeping of perspective, that this is a privilege that we get to do this, and I think that makes more generous collaborators who are willing to help each other out whenever. And are willing to make time for each others’ projects. And that is unique.

The improv comedy community here is phenomenal, and intrinsic to that community is a spirit of collaboration, and helping each other out. … It is hard to find that in LA where it’s so expensive just to survive there, that everyone is working all the time on their breadwinning projects and it’s tough to make time for the creative passions.

It is hard to find that in LA where it’s so expensive just to survive there, that everyone is working all the time on their breadwinning projects and it’s tough to make time for the creative passions. And when you’re young, when you’re hungry, it’s hard to have the perspective that like, if I don’t take this opportunity, especially when you are living paycheck to paycheck, or gig to gig, which so much of the work in this industry is; it’s very, very hard to have the privilege, the freedom, and the time to be a generous collaborator. And I think in Chicago it’s just a little bit different for those reasons. It’s easier to get from place to place, to work the logistics out…

MARTIN: You don’t have to go through all that red tape.

O’BRIEN: I would say female filmmakers, come to Chicago.

I would say female filmmakers, come to Chicago.

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