Straight-A Students in Crisis, in Olivia Wilde’s Booksmart

The director and stars Beanie Feldstein and Kaitlyn Dever chat about the cusp-of-graduation film and memories of their high school years.

In Booksmart, best friends Molly (Beanie Feldstein) and Amy (Kaitlyn Dever) are at a crossroads in their young lives. The day before they’re set to graduate from high school, the two Type-A A-students reflect on the last four years, only to realize that while excelling in their studies, they’ve failed to achieve the fun social lives of their peers.  

As they make an attempt to remedy this wrong by squeezing four years of partying into one wild night, they come to another conclusion — that their intense bond, which got them through their tempestuous teen years, had a downside: It prevented them from developing their own unique identities.

Just as Molly and Amy are attempting to prove themselves as individuals, Feldstein (Neighbors 2 and Lady Bird)  and Dever (Last Man Standing and Justified) knew that they, too, had something to demonstrate as actresses in carrying a film for the first time.

Olivia Wilde had something to prove as well. She may have already helped shoulder numerous movies, including Tron: Legacy, Better Living Through Chemistry, The Lazarus Effect, and Life Itself, but she had never directed a major motion picture till Booksmart, which opens in San Francisco on Friday.

Wilde, Feldstein, and Dever opened up to SF Weekly about pushing past insecurity, doubt, glass ceilings — and even Criss Angel — in order to graduate high school and take their careers to the next level.

What was high school like for each of you?

Beanie Feldstein: I went to a very intense academic high school where I sometimes felt like I thrived academically and other times felt I’m not going to try because everyone’s way smarter — so if I don’t try, I won’t feel like a failure. But when I watched the film, I identified most with theater kids because that was definitely who I was in high school. So it was very fun to play Molly, who hates them, and live out this evil twin of mine who lives inside me that’s making fun of it all.

Kaitlyn Dever: My high school experience was sort of half and half between real high school and homeschool because I was working a little bit at the time. But I was more of an Amy in high school. I really did love studying, and history was my favorite subject.

But I did have my phases, too. I had a phase where I was obsessed with Criss Angel for a long time, from 14 to 16. I wore black eyeliner and watched his show on TV, and my mom took me to Vegas to see his show at the Luxor. This happened until my mom said, “Kaitlyn, you can’t wear eyeliner to bed and then wear it the next day.” It wasn’t a dark time; I just liked the outfits.

Beanie Feldstein stars as Molly and Kaitlyn Dever as Amy in Olivia Wilde’s directorial debut, “Booksmart.” (Courtesy of Annapurna Pictures)

Olivia Wilde: I went to a boarding school, so it was really different in many ways, but what I discovered through this project is that there’s a real universality to the high school experience. There’s the shared trauma of adolescence and it kind of brings us all together. It’s the sense of the first time you break out and figure out who you are. You try to assert your independence, but it can be so harrowing because everything from a grade to a crush and relationship can feel like it’s going to destroy you that you really connect to a friend, and it’s a friend who gets you through it.

Olivia, there have been so many comedies made about the high school experience over the years. How do you see yours as different from the rest?

OW: A lot of films made about high school tend to be patronizing when they look back at the high school experience, “Like isn’t it quaint that they want that so badly or care so much about the party?”

So that was my first mission with this film, to say, “Let’s be honest about what it actually felt like, let’s empathize completely, and let’s make it high stakes because that’s what it felt like at that moment.” There’s a bit of wish-fulfillment, too, about what I wanted high school to feel like, and this movie is … I never had a night like this in high school.

Booksmart spotlights the intense friendships young women often form as they come into their sexuality and see the world as full of opportunities while at the same time struggling with insecurity and self-doubt. This phenomenon isn’t as common among teenage boys, I’d venture to guess…

OW: I think the difference is very interesting. Boys tend to be very good at criticizing each other at a young age, like, “Dude, that annoyed me, stop it. Get away from me.” There’s an openness for criticism that’s allowed, but it’s not as easy for them to say, “I love you, you’re beautiful, I admire you, I’m here for you, and I’ll hold you.” Physical intimacy is harder for them.

For women, I believe it’s the reverse where they can say, “I love you so much. I wish we could sleep cuddled up,” and feel safe in that. But criticism feels like a betrayal, and I think that as you evolve, you realize that real friendship involves honest criticism and that allows you to become deeper friends. But at that young age, I find that that can be very traumatizing.

BF: To continue choosing that person, as you get older, gets harder and harder and more and more meaningful. These girls continue to choose each other. But at a certain point in the final night, you see them going their separate ways and clutching at that wanting to be together but knowing they have to be apart in some way.

Olivia, this is your first time directing a major motion picture and Beanie and Kaitlyn, this is your first time carrying a film. How did you support each other on the set?

OW: I think the common thread through all of our experiences is that we all had something to prove. I was proving something and the actors were proving carrying a film for the first time. They were flexing different muscles every single day. And it was this inspired energy that was just humming, even during four weeks of night shoots where everybody could have been really tired and dragging their heels. But instead, they thought, “This is our chance.” I would have been so screwed had they not approached this with that much positivity.

BF: We, to quote Hamilton, were a group of people who were “young, scrappy, and hungry,” who thought, “We’re gonna do it right.” I, for sure, felt I had ten thousand things to prove, but the great thing is that we got to do it together. That made it so much easier.

KD: Beanie and I had never led a movie before, so it was a great thing to be able to experience it for the first time, holding each other’s hands.

Olivia, how was directing your partner, Jason Sudeikis, in Booksmart?

OW: It’s so fun to tell him what to do, although you can’t really tell him what to do. So he basically did what he wanted and it turned out to be really genius. So I was like, “Yes, yes, more, more.” I’m just his biggest fan and love the way his brain works.

You said recently that you want to direct as much as possible. Why’s that?

OW: I do because I feel like I’m so lucky to have the opportunity. It’s the best job in the world.

Better than acting?

OW: Well, I’ve always enjoyed the collaborative part of the acting process. I love when everybody’s together and coming up with ideas. But I think acting can be sort of isolating sometimes, and that’s the part I found challenging. That’s why directing is very fun for me.

And I also have to point out, for women, if you have the opportunity to direct, you should take it, because we need to prove that we can take up more space. Statistically, it’s still 4 percent of studio films were directed by women. That’s not enough, so yes, direct as much as possible.

Booksmart opens on Friday, May 24, at the Metreon 16.

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