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Katie Silberman’s Comedy Empire

The writer behind ‘Booksmart’—and ‘Set It Up,’ and ‘Isn’t It Romantic,’ and your next favorite rom-com, coming soon—is shaping a new wave of female-led, genuinely funny films. And she’s just getting started.

Getty Images/Netflix/UA/Ringer illustration

When Katie Silberman was slightly older than the characters in Booksmart, the boisterous new teen comedy she cowrote, she knew she wanted to be a writer, but not how to make it happen. The solution? “I just cold-emailed basically every writer that I liked,” she told me a few days before the Booksmart release. We were sitting at an upscale Italian restaurant on Madison Avenue, eating frou-frou chicory salads beneath a ceiling draped with bright-green hanging plants. It was the kind of cinematically gorgeous spring day when everyone already sort of looks like they’re starring in their own rom-com and anything seems possible; New York had achieved a rare and beautiful moment of sunny warmth without the standard accompanying melting-garbage smell. And yet I nearly blacked out at Silberman’s confession, remembering my mother insisting, when I was similarly young and confused, that emailing Lisa Ling was the key to starting my career. I’d dismissed this strategy as impossibly and preposterously naive. Even Silberman admits its implausibility: “I very easily could have been a crazy person,” she told me. But here Silberman was, poised in a linen sundress, flown in from her home in Santa Monica for a press tour, proof that this optimistic tactic could yield remarkable results. It sounds like a story out of a fantasy, but a normal person made it happen.

Those out-of-the-blue emails, Silberman explained, led to nurturing mentorships from established female writers, including screenwriter Dana Fox. She and Silberman became pen pals, and Fox offered Silberman an entry-level gig a few years later, after she had graduated from film school. “I moved out to L.A. and was ready to just work at a coffee shop and write,” Silberman said. “But the day that I landed, Dana Fox had a show picked up and suddenly needed an assistant.” (I need to apologize to my mom.) The show, Ben and Kate, was well-liked by critics, but canceled after one season; despite its brief run, it served as a valuable launching pad for Silberman’s career. She got along so well with Fox that they partnered up on script rewriting projects, including work on the Rebel Wilson–led Isn’t It Romantic?, which gave Silberman the confidence to work on solo projects. “The first script I ever wrote myself was Set It Up,” she said. (Mom: I am so sorry.)

The 2018 Netflix original, a kicky rom-com about two harried assistants who fall in love while setting up their finicky employers, was a hit for the streaming service and a showcase for Silberman’s witty, good-natured sensibility. While her dynamic with a powerful female figure put her in the position to get Set It Up made, Silberman stressed that it in no way served as the movie’s inspiration. “Set It Up is about all these terrible bosses, and I only had one boss and she was extraordinary and as generous and gracious as anyone could ever be, and one of my best friends.” (The workplace in Set It Up, however, was inspired by a real-life sports media startup. “It was based on The Ringer,” Silberman said.) (She also said it was based on Deadspin. But whatever.)

The success of Set It Up meant that Silberman was invited to pitch her take on Booksmart. That pitch led to her working with Olivia Wilde, who directed the film, and who was so taken with Silberman’s work that the pair are already planning their second project together. “Developing the script with Olivia was probably the most fun I’ve ever had in my life,” Silberman said. And the success of Set It Up, Isn’t It Romantic?, and Booksmart have rapidly made Silberman one of the highest-profile comedy screenwriters in the country. A solid return from some unsolicited emails.

A screenplay for Booksmart, written by Emily Halpern and Sarah Haskins, had been around since Silberman graduated from Dartmouth in 2009—the same year it wound up on the Hollywood Black List for promising unproduced screenplays. Despite the positive response within the industry, Halpern and Haskins’s story, about two overachieving best friends who decide to become party animals for one night before graduating high school, was stuck in development purgatory for years.

Even after a freshened-up draft by writer Susanna Fogel in 2014, the movie’s future was uncertain. It had been a weird decade for funny movies. Studios were chasing tentpole blockbusters that would translate to global audiences, which was bad news for comedy, which tends to be mid-budget and also not particularly well-suited to kill internationally, as so much of humor is language- and culture-dependent. The rom-com flourished in the indie world, and there was the occasional Bridesmaids-like hit, but it was a tricky time to get this kind of movie in theaters. Katherine Heigl’s career shriveled. It looked like television might usurp film as the place for audiences to find light entertainment about the attractive, funny, and lovelorn. And in 2018 that turned out to be true, at least in terms of the literal screen we use to watch romantic comedies. Along with Crazy Rich Asians, which demonstrated that the right romantic comedy could still be a potent box office draw, To All the Boys I’ve Loved Before and Set It Up both found wide, enthusiastic audiences through Netflix.

Thanks to Set It Up’s success, Silberman was invited to pitch a refresher on the long-stalled Booksmart project. Wilde was attached to the project at that point and had a very specific vision for her debut. “Her pitch was that the movie was Training Day for high school girls,” Silberman said. “That’s the level of intensity that high school girls deserve.” Silberman wanted to root the movie in the very valid but heightened emotions evoked by social situations in high school and inserted a new catalyst for the movie’s “One Crazy Night” story line that reflected this. When Amy and Molly (Kaitlyn Dever and Beanie Feldstein) discover that the classmates they’d dismissed as irresponsible party-animal slackers were actually every bit as accomplished as the rule-following duo, they decide to join them at a pregraduation rager to show that they’re well-balanced too. “Their existential crisis is realizing that they’ve judged everyone incorrectly,” Silberman said. “I was excited to lean into what these people would have been in a traditional high school movie, and then reveal them all to be something a little more than that.”

One of Silberman’s skills is this habit of lovingly tweaking storytelling tropes so that they feel less stuffy. Her affection for the genres she most frequently works within is obvious, as is her desire to open them up a bit. Booksmart shares DNA with the teen movie Superbad, which also follows a pair of high school BFFs on one last adventure before graduation. Both films are anchored in a central friendship, feature a memorably wacky cast of supporting characters, and showcase a Feldstein sibling as the fast-talking and more confident member of the main duo. (Superbad’s Jonah Hill is Beanie Feldstein’s older brother.) Booksmart also overlaps thematically with Greta Gerwig’s Lady Bird, in its specific Californian setting, focus on supportive female friendship, and the casting of Feldstein. Despite drawing on its predecessors and on the general arc of teen comedies that revolve around one wild party, Booksmart still feels fresh. It melds the raunchiness of Superbad with the gentleness of spirit of Lady Bird and also firmly situates itself in the world teenagers inhabit in 2019. “I immediately fell in love with Molly and Amy’s friendship,” Kaitlyn Dever told The Ringer via email. “It was unlike anything I had ever read before.”

Although the original screenplay had been written more than a decade earlier, the end result is a modern comedy, one that takes place in a hyperprogressive enclave among Gen Z characters who actually look and talk like they were born after the year 2000. “In order for a movie like this to work,” Silberman said, “it really needs to be specific about the generation.” She was inspired by Bo Burnham’s dedication to realistically capturing the younger generation in Eighth Grade and made sure to interview real teenagers and to lean heavily on the cast’s own sense of style and personalities. The high school milieu in Booksmart is deliberately free of villains, with a tender attitude toward its cast that distinguishes the film from equally funny but sharper-edged teen comedies like Mean Girls. This is a raunchy movie—there are plot points involving butthole fingering and unconventional masturbation choices—but it’s never a rude movie. The weirdos, particularly Billie Lourd’s ethereal maniac Gigi and Skyler Gisondo’s well-meaning hypebeast Jared, are misfits but not outcasts, and the popular kids like Molly Gordon’s blowjob-loving future Yalie “Triple A” tend to complicate their reputations rather than totally reject or fulfill them. “We wanted to develop all these tertiary characters into people that had a full arc and could’ve had their own movie,” Silberman said. As in the underrated 2018 teen comedy Blockers, Booksmart has a gay protagonist whose sexual identity is important to the plot and her character—Amy is queer, and spends the movie trying to kiss a girl for the first time—but not a social vulnerability. The school hierarchy portrayed in Booksmart underlines how attitudes about gender identity and sexuality have shifted for younger people in very blue pockets of the country.

The total lack of assholes definitely places Booksmart into feel-good fantasy territory, but it doesn’t sap it of its central conflict, which is about how Molly and Amy have to learn to let go of each other as they move into a new phase of their lives. “We realized that we needed to structure it and kind of keep looking at it, all the time, as a breakup movie,” Silberman said. “It’s about the end of a kind of friendship. That even if you stay friends with that person forever, which I think Molly and Amy will, it’s irrevocably changed by the end of school.”

While Silberman’s characters have to learn to say goodbye, she is developing a rotating group of people she will work with repeatedly.

This is no doubt helped by how much people Silberman works with seem to like working with her. “She is quite possibly the greatest person on this earth,” Dever said. “I’ve yet to meet a person who has worked with Katie and has not begged to work with her again after it was over,” Zoey Deutch said by email. “She is my wife.” To that end, Silberman is already working on a new female buddy comedy with Wilde and has reunited with Set It Up stars Deutch and Glen Powell for a new project currently in production. “They’ll be playing new characters in a new world,” Silberman said. “That is going to be kind of like an action romantic comedy, à la Romancing the Stone.” Deutch said she plans to start begging for a third movie soon.

Meanwhile, Silberman is looking forward to paying tribute to her mentors by helping plucky strangers in the same way she found help after a few fortuitous emails. “I’m really excited about finding younger writers, especially writers who have a totally different perspective from mine, and helping to shepherd projects,” she said. True to her unfailingly supportive word, Silberman insisted on emailing me her personal address to make sure I had everything needed to successfully tell this story before she headed to Brooklyn to meet with Wilde to discuss their next project. Like the women who received her messages when she was just starting out, I wanted to keep the conversation going.

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