Olivia Wilde's Directorial Debut Is Changing The Game For Queer Teen Movies

“We wanted to tell a story that moved beyond what we typically see when it comes to queer characters, when it’s all about the coming out,” Wilde told BuzzFeed News about Booksmart. (Warning: SPOILERS.)

The day after Booksmart debuted at the SXSW Film Festival in March, the team behind the acclaimed teen comedy appeared in a panel together to discuss the film, about two overachieving high school seniors, Molly (Beanie Feldstein) and Amy (Kaitlyn Dever), and their mad scramble to reclaim their social lives the night before graduation. Roughly 45 minutes into the hourlong panel, a woman in the audience stepped up to a microphone and asked about how the filmmakers approached Amy’s queerness.

“For somebody who identifies as gay, and has seen a bunch of gay and lesbian roles onscreen, I really have to applaud you guys,” she said. “You guys, like, nailed it — making it so realistic for girls that age. … How did you do it?”

Wilde answered by saying she wanted to treat Amy’s sexuality the way she thought her peers would: by making it “a nonissue,” a sentiment that screenwriter Katie Silberman then echoed. “Our friends who identify as queer, it’s like the fifth thing you would mention about them, if not the 15th,” Silberman said.

Then Feldstein spoke up.

“It was really meaningful for me to watch the film,” she said. “My partner’s a woman.”

“I think if I could have seen our film earlier, I think I maybe would have found myself a bit sooner.”

Feldstein spoke these words with such matter-of-fact composure that one could be forgiven for not realizing that she had, in fact, just publicly come out. The 25-year-old actor, whose career exploded in 2017 as Saoirse Ronan’s BFF in Lady Bird, explained how moved she was during Amy’s climactic love scene in the film, especially because Wilde and Silberman chose to emphasize the human, awkward moments often cut out of teen love scenes, like the clumsy struggle it is just to take off your own pants.

“Representation is really important,” Feldstein said. “I think if I could have seen our film earlier, I think I maybe would have found myself a bit sooner.”

No one onstage remarked on Feldstein’s nonchalant revelation, but the moment was not lost on other women panelists. “I was really proud of her,” Wilde told BuzzFeed News last month before Booksmart’s nationwide release. “I was like, I wonder if that will become a story. I wonder if that’s going to affect her or her career.

It did become a story, but barely. The New York Post ran an item that day with the vague headline Beanie Feldstein opens up about sexuality,” which was then aggregated by several other outlets — People, Bustle, HuffPost — with similarly nebulous headlines. When Feldstein was subsequently interviewed in advance of Booksmart’s theatrical release, she expanded on her SXSW revelation. (To the Wall Street Journal: “I was like, I’m not gonna not address it, because it is my truth.” To New York magazine: “I was sort of like, Men? Sure. Then I met my girlfriend and I was like, Oh no, this is love. This is what being in love feels like.”) None of those pieces, however, made Feldstein’s sexuality the centerpiece of their story.

Let’s compare, for a moment, that reaction to what happened when, on May 31, the New York Times ran an interview with the actor Richard Madden in advance of his supporting role as Elton John’s boyfriend and manager in the musical biopic Rocketman. A few months before Rocketman’s release, paparazzi photos of Madden and actor Brandon Flynn (i.e., Sam Smith’s ex), matched with some social media sleuthing, had led to wide speculation that Madden and Flynn are dating. The Times’ Kyle Buchanan asked if they are.

Madden’s reply, in a manner Buchanan characterized as “unbothered”: “I just keep my personal life personal. I’ve never talked about my relationships.”

His nonanswer about his sexuality certainly delivered far more widespread press coverage than Feldstein directly addressing hers (getting to put “Game of Thrones” in a headline can do that to a story). But his decision not to engage with the context of the question also weirdly echoed the film’s essentially shallow approach to queerness in general, reducing Elton John’s overabundant life into the story of a troubled rock star learning to accept himself enough to come out to a world that had long surmised he was gay anyway.

Meanwhile, much like Feldstein’s approach to talking about her sexuality, Booksmart at once centers its characters’ queerness while also treating it as a simple fact, not an issue to be surmounted or hardship that has to be endured. In doing so, the film — and its stars — are charting a new future for queer films and queer actors. This is how they got there. The question is, will audiences follow?

Although queer teenage characters have become much more commonplace on TV over the past two decades, it wasn’t until last year that a mainstream, wide-release teen movie — the romantic comedy Love, Simon — featured a gay lead character. It turned out to be the first of several films last year featuring queer teens, from the raunchy studio comedy Blockers (about three BFFs who make a sex pact for prom) to the sober indie drama Boy Erased (about gay conversion therapy). In just about all of them, however, the queer characters were either struggling to come out, or struggling with accepting their sexuality after being outed against their will.

With Booksmart, Wilde wanted to do something quite different.

“We wanted to tell a story that moved beyond what we typically see when it comes to queer-identifying characters, when it’s all about the coming out and the stress around it,” she told BuzzFeed News.

In the original script for Booksmart, which appeared on the 2009 Black List of the hottest scripts in Hollywood, Amy was straight, and she and Molly had set a pact to both find boyfriends by prom. By the time Wilde was hired to make her feature directing debut with Booksmart, however, the film had already undergone some significant changes, including making Amy gay.

Working with screenwriter Katie Silberman, however, Wilde created several more queer-identifying characters who, crucially, had accepted their sexuality and come out to their peers, including George (Noah Galvin) and Alan (Austin Crute), the two delightful leaders of their school’s theater department. Rather than a single token queer character burdened with representing all things for all LGBT people, Booksmart’s queer characters are woven fully into the fabric of its story — their sexuality is part of the larger narrative, but not the point of the narrative.

“We don’t just say that Amy is queer, and then we move on from it.”

“In the past, the gay characters that I’ve seen in film almost always feel like they were put in the movie to be the gay character,” Dever said. “The thing that was so cool about Amy was her sexuality was not a defining characteristic.”

For LBGT audiences, making sure a queer character isn’t “defined” by their sexuality has long felt like code for not having any sexuality: They’re there to be quippy and chic, help the straight characters resolve their own dilemmas, and maybe enjoy a brief flirtation or a chaste kiss. But Amy’s entire arc in Booksmart pivots precisely on the tried-and-true teen movie tradition of chasing after her long-standing crush, culminating with her first sexual experience — and the film’s only sex scene.

“We don’t just say that Amy is queer, and then we move on from it,” Dever said. “We actually see her explore her sexuality in this movie.”

“[Amy’d] come out to her friends and family and it was wasn’t an issue for them, but like so many young teenagers of any sexuality, she hadn’t had any experience yet,” said Wilde. “I want this character to be defined by so many things: her intelligence, her activism, her love for her best friend, her curiosity, her sweetness, her humor, and of course, PS, also, she’s queer and that’s what she’s dealing with right now in terms of her crush.”

If that sounds a lot like how one might describe all manner of straight, cis teen characters from every teen movie ever, that’s pretty much the point. “Coming-out stories — they’re important to tell,” said Galvin, who came out publicly at 21 when his ABC sitcom The Real O’Neals, about a gay teenager coming out to his family, debuted in 2016. “But I think we’re at a time where, over and over again, replaying the plight of the queer person, which often is told, like, through a negative coming-out story — I’m done with seeing that story. I want to see queer characters just live lives.”

Wilde’s first break as an actor came when she appeared on the second season of the seminal mid-2000s primetime teen soap The O.C. as Alex Kelly, a bisexual teenager who dates both Adam Brody’s Seth Cohen and Mischa Barton’s Marissa Cooper.

“In the moment, I didn’t think anything of it,” Wilde said. “I was like, she is cool and confident, she loves music — you know, I was thinking about other things. Then the show came out, and it was a sensation that she was queer. I didn’t even understand the significance of what we were doing. I was just playing a person.”

It wasn’t until a few years later that the true significance of Alex’s character began to sink in for Wilde. “I’m not exaggerating, this still happens to me, people come up to me and say, ‘Your representation in that show allowed me to feel comfortable with myself, or allowed me to come out to my family or my friends, or allowed me to realize I didn’t have to be the stereotypical version of what I feared being queer meant,’” said Wilde. “I am really moved by that. I take it very seriously. And it has affected the way that I want to tell stories, because it made me realize the extensive reach of the stories we tell. We don’t know who’s watching and who might need to hear or see something to help them.”

That lesson even carried over into the auditions for Ryan, Amy’s crush in Booksmart. The character breakdown for the role noted Amy’s infatuation with her, and that Amy isn’t sure what her sexuality is. “So all these actresses came kind of embodying what I would consider a sort of stereotype of a young, queer woman,” Wilde said. “I was like, What’s happening here? Why is everyone doing like, their butch impression or something. … What subtle messages are we sending into society that cause stereotypes to exist? So much that actors think, like, OK, she probably walks and talks like this.”

The experience caused Wilde to focus even more on ensuring that every character in Booksmart felt like a real person as opposed to a cliché. “I started telling people, ‘Just forget the part where Amy thinks Ryan might be gay. Just take that out,’” she said. “It was becoming so distractingly big in terms of the interpretation of the character that it was causing people not to dive deeper into, like, what else is she like?”

Wilde said that the actor who eventually got the role, Victoria Ruesga, told Wilde that she saw Ryan as just really nice, which throws off Amy’s ability to parse her attraction from Ryan’s kindness.

“I was like, ‘Exactly, exactly, my friend, you are so hired, I love you,’” she said.

Wilde stumbled on a different kind of queer stereotype when she was auditioning actors for Alan, who was initially written to be the gay best friend of the school’s overly enthusiastic theater queen. Both Galvin and Crute read for the role, and Wilde became so enamored with both actors that she and Silberman decided to change Alan’s female counterpart into to a male one, George, played by Galvin.

“We were like, you know, maybe we can move beyond the trope of the girl with her gay best friend,” she said.

Both Galvin and Crute were, understandably, thrilled with the change. “We’ve all seen the Ryan/Sharpay dynamic portrayed before,” said Crute. “We all know what that is. Usually the gay character is the best friend, the condiment, the side item, the seasoning. The fact that the queer energies can take control and be the beacon by which we see the theater program … it’s just refreshing.”

Initially, Galvin and Crute were only meant to be in one scene at the start of the film and then appear in the climactic graduation ceremony. But Wilde was so taken with what they were doing that she and Silberman created an entire sequence set at a murder mystery dinner party held at George’s house, just so the film could spend more time with them. Then Wilde asked Galvin to show up for the cool kids party scene in the third act, which led to Galvin rocking out to an outrageously fabulous drunken karaoke rendition of Alanis Morissette’s “You Oughta Know.”

Annapurna Pictures

Galvin singing “You Oughta Know” in Booksmart.

“It was insanely collaborative — we would sort of just let the moment dictate the next,” said Galvin. “We felt that George had an anger that could very easily maybe also possibly be unrequited love. So I thought that George being inebriated in the karaoke scene would be a moment where he could unleash a little bit and let go of the feelings that he’s been holding inside that just happened to be for Alan.”

That kind of layered thoughtfulness is rare for a teen movie, and rarer still for a queer teen character. “It specifically allows the queer characters in the film to have rich interior lives, you know?” Galvin said. “A big problem with a lot of depictions of high school in cinema is that a lot of these characters are so goddamn one dimensional, and you know, at the end of the day, just boring because of that.”

Crute’s decision to play Alan as unapologetically effeminate, meanwhile, might have felt like exactly the kind of one-dimensional stereotype that had caused LGBT audiences in the past to worry if the role was good for the gays. But Crute, who said he had to suppress his own sexuality growing up in a conservative Christian community, saw the role differently.

“I actually took inspiration from myself, because I feel like I’m five different types of queer people in one person,” he said. “When I’m around my straight guy, masc friends” — he grunted — “I’m this masc guy, you know. I go with that energy. When I’m around my girl friends, I’m a queen.”

Crute said he imagined Alan growing up in a family in which he was given the freedom just to be gay without judgment of how he expressed it. “I just experimented with not being afraid of being femme,” he said. “A lot of times when the character is femme, it’s seen as like a parody or comedy. It can add to comedy, absolutely. It can accompany it. But I think that femme queers are valid. Queer characters sometimes are portrayed as straight-acting and straight-looking gay people. And it’s like, it’s OK to portray gay-looking, gay-acting gay people, and still recognize them as valid human beings that can be taken seriously.”

Even with all the intensive time spent bringing as much specificity to its queer roles as possible, the climatic scene in Booksmart, when Amy finally has her first sexual experience with another girl in her class, Hope (Diana Silvers), has raised a few eyebrows. After some awkward fumbling on the floor of a bathroom at a house party, Amy begins to finger Hope, until Hope whispers, “I don’t think that’s the hole you think it is.”

“As a woman who has had plenty of slapstick sexual experiences with other women but never managed to mistake a butthole for a vagina, I was confused,” wrote Christina Cauterucci for Slate. “I wondered: Does this actually happen to people?”

When I asked Wilde about Amy’s slip up with Hope, she explained that the scene was in the draft of the script before she and Silberman signed onto the film, but it was meant much more as a classically slapstick comedy beat.

“Everything got really crazy and broad,” she said. “I leaned away from that. I was like, Listen, I can maintain this moment of Amy messing up, because I thought, you know, exploring the anxiety that comes from discovering your sexuality, that’s interesting to me. But I didn’t want to make it really slapstick-y and broad, because I didn’t really feel that was within the tone of the movie we’ve made.”

Queer representation is still so incredibly rare in pop culture that Amy’s tactile inexperience with basic female anatomy could easily translate as the filmmakers’ ignorance about how women have sex with women. Wilde and Dever do both identify as straight, though they were both quick to note that they saw Amy’s furtive sexual encounter as relatable to anyone.

“In hookup scenes that I’ve seen in movies, they make it look, like, pretty seamless and easy, and, like sexy and cool. But it really isn’t.”

“The feeling of being nervous and never having like any sort of hookup moment in your life, if you’ve never kissed anyone before, that’s a universal feeling,” Dever said. “In hookup scenes that I’ve seen in movies, they make it look, like, pretty seamless and easy, and, like sexy and cool. But it really isn’t. We wanted to keep in all of those awkward moments that you have when you’re hooking up with someone for the first time.”

Dever also pointed out that the scene also plays to the film’s titular premise, that Amy and Molly are “very, very, very smart, but not very wise.”

That’s another trope of queer characters that Booksmart quietly tries to dismantle: They’re always supposed to be savvy. Even Cauterucci in her Slate piece concludes that there probably have been some unlucky queer teens whose fingers have, in the heat of the moment, mistaken their intended target for one nearby — at least, there’s enough of a possibility that we can believe it could happen in a movie, just like there have been some straight teenage girls who have probably kissed their ex-stepbrothers, and some straight teenage boys who have probably fucked a pie.

“It’s not that she does anything terrible,” Wilde said of Amy’s mistake. “When you’re young, you can do something that is so innocent, and not at all terrible, and yet, in the moment, it can feel so mortifying. And I thought, well, this is an opportunity to share that experience.”

When I asked Crute if he was comfortable telling me how he identified his sexuality, he paused for a moment before answering.

“Just right now, I’m bi as far as I know,” he said. “The last relationship I had was with a girl, but you know, now I’m full-on guys right now. Like, I’m in a guy season. You know, feeling it out — it’s a spectrum. And while I’m figuring it out, hopefully, I can help other people figure it out.”

Booksmart is Crute’s first major film role — he auditioned for the film while on spring break at NYU — and while his candor is totally in keeping with his generation’s evolving attitudes about sexuality, it remains atypical for a young actor just launching his career. Crute will next appear in another queer role on the Netflix sci-fi dystopia series Daybreak, and yet there is a vast catalogue of queer actors who’ve played multiple queer roles who have chosen to remain publicly silent about their own sexuality.

For Crute, the decision to start his career being so transparent about his own life was not a simple one. “I was like, am I gonna kill my grandparents?” he said with a laugh. “Am I going to affect, you know, my mom’s reputation? She still runs the church.” Ultimately, however, Crute couldn’t step back from what he sees as an opportunity to provide the kind of representation to kids like him that he’d never had a chance to see growing up.

“Even in my queer infancy, it’s been therapeutic for me,” he said of doing Booksmart. “Because I am basically ministering to a lot of kids that feel too feminine, or too much, or too extra, or too this or too that, when you can really just be who you want to be, and who you need to be.”

“I don’t consider any kind of love off limits for myself, or anyone else.”

It’s a sentiment echoed by Wilde after I asked her how she self-identifies. “Oh, I’m straight. That’s totally a valid question,” she said. “But, you know, I sort of personally reject labels in general, partially because I have this awareness of the kind of fluidity of identity in life and how we continue to evolve. I’m certainly not the same person I was at 21 — I hope not, Lord — and I don’t know who I’ll be in 20 years. There’s something about labels that feels sort of restrictive in terms of our own evolution. I don’t consider any kind of love off limits for myself, or anyone else.”

Wilde infused that sensitivity into Booksmart’s bones, but it’s unclear how many people will get to experience it for themselves: To date, the film has grossed a meager $14.3 million at the domestic box office, discouraging for any teen comedy, but especially one with Booksmart’s sterling critical reception. The culprit, to be clear, does not appear to be the film’s queer representation — Annapurna Pictures seems to have wildly miscalculated audience appetite for a teen comedy against behemoth summer blockbusters like Aladdin, Godzilla: King of the Monsters, and Avengers: Endgame.

So Booksmart’s creative breakthroughs weren’t matched by a financial one, an all-too-common story for queer-centered movies. But like so many other queer-centered movies before it, there’s every chance this movie will find its audience — it’s just too good not to.

“I think about kids living in more repressive communities with families that might not see them,” said Wilde. “And that they will have a chance to watch this movie and think like, Oh, there’s high schools out there where it’s not a big deal that I’m gay. Yeah, there’s a version of the world that I believe is very real for some kids, and not for others. I’m hoping that someone out there will feel like there’s a reason to hold on a little bit, because they have a family out there.” ●

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