'Booksmart' Screenwriter Katie Silberman On Crafting A Unique High School Movie And The New Wave Of Romantic Comedies [Interview]

When I first watched Booksmart during its world premiere at SXSW, I fell in love with this high school comedy in an instant. When we talk about the films that we wished we had while growing up, this is one of them. It feels like an instant classic. Kaitlyn Dever and Beanie Feldstein are both phenomenal in the film and I couldn't stop laughing at every ridiculous and wonderful joke.

Booksmart screenwriter Katie Silberman (she shares screenplay credit with Emily Halpern, Sarah Haskins, and Susanna Fogel) spoke with /Film over the phone this week to discuss the writing process as well as favorite high school comedies. Before the world premiere, I chatted with Katie Silberman on the red carpet. Some of that conversation has been edited into the transcript of our phone conversation.

Annapurna opens Booksmart in theaters on May 24, 2019.

It's been a great few years for you with Set It Up, Isn't It Romantic, and now Booksmart.  When I saw the film at SXSW, I felt it was an instant classic.

Thank you!

Many of us look at Bridesmaids when it comes to female friendship, how exciting is it to be able to add Booksmart to the list?

Oh my gosh. I mean that's the highest compliment imaginable. That's the dream. If you had told me beforehand it would be compared to that, I would have told you truly that is kind of a dream come true especially because when we were developing the movie and the story, Olivia Wilde and I knew which high school movies had inspired us. We talked a lot about Clueless, Dazed and Confused, Fast Times at Ridgemont High, and The Breakfast Club. When we asked young people in high school and just out of high school, "What's your favorite high school friendship movie," a lot of times they would answer Bridesmaids. Even though it wasn't in high school because that was the movie that they felt kind of most accurately demonstrated female friendship—that was the most authentic female friendship they had seen on screen. It was so funny that that is the bar that we set for ourselves and I think should be set for kind of all writers who are trying to write female friendship. I also don't think it's a coincidence that that movie was written by best friends Annie Mumolo and Kristen Wiig, who love each other so much and are able to infuse that friendship and that intimacy into what they were doing on the page. That was for us always kind of the bar to reach and the goal to set that was to be part of that especially because I watch Bridesmaids 17 times a year—if I have a cold or if I'm on a long flight, I can always watch Bridesmaids. If people are able to watch Booksmart that many times, I would die happy.

I'm already at two times and I'm probably going for the third time over the weekend.

Oh, good! That makes me so happy.

Molly and Amy didn't really party in high school until the eve of graduation.  Was your own high school experience any similar?

In a lot of ways, this movie is kind of wish fulfillment for me because I was kind of a Molly in high school if I had not had this realization and simply graduated without ever really going to any parties. I thought I was being responsible. I thought I was being very forward-thinking by only focusing on academics and taking myself very seriously. It wasn't until my 20s that I realized that that wasn't responsibility as much as it was probably fear and insecurity and that I just wasn't putting myself out there because I was nervous. I wish that I kind of had the kick in the pants that Molly has in this movie to force herself to do something because I would have loved to have learned that earlier rather than later.

Can you talk about your writing process for the film?

I came on with the director, Olivia Wilde, already attached and so it was a really fun experience to take in the clear vision of what she wanted to do and translate that into the script as it evolved.  I came on in September and it happened pretty quickly.  We finished our draft by January.  It was really fun also because the script was really able to evolve throughout the entire process, not just when we had a greenlit draft.  We did a lot of rewrites through casting as we had this incredible cast that we were able to adjust to, through preproduction as you find locations and realize your timeline and what you want to do, and on set as well so it was a really fun evolution from beginning to end.

Speaking as someone who is trans, one of the things that I love about Booksmart is that Amy being a lesbian isn't seen as being a big deal.

Absolutely, yeah. There have been so many wonderful coming out stories made recently that are really important and I've thought have been so well done. We were really excited though about the opportunity to tell just a love story for someone—kind of the next phase of your life—after you've been through that that momentous story yourself. We talked about Amy is queer but that's not the first thing you had mentioned about her—a lot of times in movies the queer character, that's their defining characteristic but being straight is very rarely someone's defining characteristic. It's one of many things about them and you would say a lot of other things first. That was the world in which we wanted to address Amy as well. We wanted to give her a crush and a wonderful love story. I think she probably had the most fun love story of everyone in the movie but it was one facet of her personality and didn't need to be the only one or the dominating one.

Going back to your work on Set It Up, I feel like it kickstarted this whole new wave of romantic comedies.

Thank you—that makes me so happy! It was so fun to make that at Netflix because it was hard to make that at a studio. Netflix was the one who came in believed and was like, "We think people really want this.  We're willing to take a risk on it." For it to result in what it did, it was really fun.

After the success of Set It Up, you're writing Most Dangerous Game for Zoey Deutch and Glen Powell set to be released on Netflix in 2020.  Is there anything that you can tell us about the film?

First of all, I feel so lucky for the opportunity to make another movie with them. I think they are geniuses and they have such wonderful chemistry. They're also such wonderful people so just the opportunity to spend more time with them is very exciting for me. We were really excited after Set It Up, which we had such a wonderful experience on and it felt like kind of a perfect experience for us in and of itself. We were thinking about our favorite heroes from the rom-com world and not to compare ourselves to them because they're quite geniuses but how the people that we really loved like Spencer Tracy and Katharine Hepburn or Tom Hanks and Meg Ryan. They very rarely make sequels. They took the wonderful chemistry that they had and put it in a new world with new characters and got to explore a new world in the next movie. We were thinking about the kinds of rom-coms that we loved and we felt like Set It Up was the kind of often screwball rom com and but another kind of rom-com that we haven't seen in a while that we've always loved is the action rom-com like Romancing the Stone. This next movie is kind of like a modern Romancing the Stone with the two of them set today but that of kind of fun swashbuckling action comedy.

What are some of your favorite high school comedies while growing up?

I love Clueless.  I love Clueless so much. I love everything that Amy Heckerling does but Clueless really was pretty monumental for me. I loved Mean Girls. I loved The Breakfast Club. I loved Dazed and Confused. I loved Fast Times at Ridgemont High. I loved Superbad. Did I say Mean Girls? That came out when I was in high school and that was—I remember that's the kind of movie where we're in the first few minutes and you're like, Oh, this is the funniest movie I'll ever see. I'm in no matter what else happened. Those were the ones that we talked about when we were developing in terms of how do we make a movie that makes people feel the way those movies made us feel.

I just rewatched Mean Girls for the 15th anniversary. It's hard to believe it's been that long!

I can't believe it's been 15 years. That makes me feel 107. If you had told me it had come out last year, I would have believed you.

Some of these classics feel like they just came out yesterday!

I know! What's even crazier is I would imagine that Clueless is close to 30 years old and that really feels like it's a part of my everyday life. Superbad came out twelve years ago. That one really blows my mind.

I think Clueless is around 24 years old. I know they just had a reunion in Chicago with four of the cast members.

That's so fun! It's crazy because I feel like I know people who are 24 and the fact that they were born the year that came out feels like it should be illegal.