10 Things I Hate About You was written largely via snail mail. Karen McCullah and Kirsten “Kiwi” Smith, the screenwriters behind the landmark teen romantic comedy, wrote the film while in a long-distance writing partnership. They had met around 1996, when Smith, who was working in a cubicle at a development gig in Hollywood, came across a script of McCullah’s in the submissions pile and took interest. They bonded first via mail, then over the phone, then in person, quickly becoming a team that’s lasted over two decades and has churned out some of the most quotable films of the past 30 years — including but not limited to 10 Things, Legally Blonde, She’s the Man, and The House Bunny. The first script they sold was 10 Things, and since they were still living in different cities at the time, they wrote it by taking turns mailing pages back and forth via the express delivery service Airborne.
By the time 10 Things hit theaters, the duo was already working on another project: the film adaptation of the not-yet-published Amanda Brown novel Legally Blonde. The two movies formed a one-two punch introduction to Hollywood that should ensure, if there is any creative justice left in the pop cultural realm, that McCullah and Smith are forever immortalized as legends — the craftswomen behind two of the industry’s most enduring films.
“I think our legacy is just these fearless, funny female characters who are sort of radical by their confidence,” Smith said about the pair’s footprint in Hollywood. “They’re changing the world even though they don’t really know that they’re doing it.” McCullah described their work in her own five words: “badass and full of mirth.”
The first screenplay Smith and McCullah worked on after meeting for the first time in real life was a women-led action comedy. When that film didn’t sell, they started contemplating their next steps. “We knew we wanted to write a teen movie, and we got the inkling that we wanted to adapt a classic story,” Smith said. She recalled that while teen movies at that point weren’t “really, fully in the zeitgeist,” she and McCullah had admired Clueless, Amy Heckerling’s take on Emma, and were looking to utilize a similar formula. They already had the title for their new movie, inspired by a list McCullah had kept about a boyfriend, and they landed pretty quickly on William Shakespeare’s The Taming of the Shrew as the play they wanted to reinterpret for modern times. “We definitely knew [the title character] would not be tamed at the end,” McCullah said.
Luckily for Smith and McCullah, Disney happened to be looking for a teen movie to make right as the pair had gotten the script into fighting shape. “They had purchased another script at the time, called School Slut, and it was this race to see which rewrite would come in better, our script or School Slut,” Smith recalled. The rewrite of 10 Things won out, and the rest, indeed, is history.
In 2018, 10 Things is remembered alongside its foremother Clueless as one of the most well-crafted, beloved teen movies out of the ’90s. Released in 1999 and directed by Gil Junger, the film is known in part for launching Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt into superstardom, as well as for embedding several Letters to Cleo songs into the imagination of a generation. Smith and McCullah’s screenplay was the bedrock to the film’s success. The script is punchy and clever, but also cutting and sweet in the same breath. The writing provided rich material for the movie’s actors and director to play around with, and everyone involved in the movie excelled at bringing the story to life. The film’s characters, as reimagined from Shakespeare and molded around Smith and McCullah’s sensibilities, are so incisively written that they stand as timeless archetypes that modern teen movies, from Mean Girls to The DUFF, shamelessly pull from — while also being quintessential emblems of American teen culture in the ’90s.
“We did get a note that said, ‘Why is she so angry?’”
The character of Kat (Stiles), in particular, remains a prescient portrayal. The “shrew” in question from Shakespeare’s original title, Kat is an unapologetically angry teen girl. A constant scowl on her face, she is combative, hostile — “the mewling, rampallian wretch herself” — and stomps around her privileged Seattle life in granny dresses, spouting ideas from feminist literature and yearning for a future life at Sarah Lawrence College. It’s not exaggeration to call Kat a masterpiece. She’s a moving time capsule to a specific slice of riot grrl–inspired, indie music–loving, agitated, alternative, usually-white girl culture of the era.
When Disney execs first met Kat, in one of the early drafts of 10 Things, McCullah said, they couldn’t quite wrap their heads around why she was so pissed off all the time. “We did get a note that said, ‘Why is she so angry?’” Smith said. According to McCullah, “they didn’t understand that sometimes as a teenage girl you’re just angry at all the bullshit you have to put up with.” The executives pushed the writing team to add a specific backstory to explain Kat’s anger issues. Eventually Smith and McCullah yielded, writing in a throughline about Kat and her sister Bianca’s (Larisa Oleynik) mother having abandoned the family.
The generation that first made 10 Things a hit is grown now. By all accounts they’re still pretty obsessed with the film, as are many of the people who’ve found the film since its release. “It’s only gotten more love over the years,” Smith says, “which just feels so lovely, to have the passionate response from younger generations, that the movie means something to them in their youth and in their evolution. What could be better than that?”
Riding off the buzz from 10 Things in the late ’90s, Smith and McCullah dove right into adapting Legally Blonde. “When we read [the novel] we just thought, wow, this is such a gift, what a great concept, what a great character,” Smith said. “So many bare bones of the plot were architected in Amanda’s book, and that’s what you want. We knew that we knew how to do it.”
Even more so than 10 Things, Legally Blonde pivots on one central woman character in conflict with the world around her. Elle Woods (Reese Witherspoon) is a chipper sorority girl from Southern California who applies and gets accepted to Harvard Law School in a ploy to win back her ex-boyfriend. Once at Harvard, Elle responds to her peers’ skepticism over her presence by setting out to demonstrate that she’s got what it takes to succeed in this new, notoriously challenging environment.
“Her confidence and her optimism are big parts of her character. Other people might underestimate her, but she never underestimates herself,” McCullah said of Elle. She also noted that the very concept of the character was a reversal of the norm when the film came out in 2001. “A lot of time in movies the rich, pretty, popular girl is the villain instead of the underdog,” McCullah said. “It was fun to play with that dynamic with [Elle] being the underdog, having to prove herself to other people even when she was completely capable.”
Developing Elle Woods for the screen took time and precision. The character is bubbly, style-oriented, and at the beginning of the film is happy existing in the perfectly-manicured world she grew up in. She’s also determined, and observant, with an empathy her peers at law school often lack and an ability to rebound when her dreams don’t pan out as planned. According to Smith, the editing process for the screenplay involved a lot of layering in moments “that made sure it was clear that [Elle] was very keenly intelligent” without sacrificing her earnest pep. One of the manifestations of Smith and McCullah’s efforts came in the form of a scene early in the movie where Elle schools a salesperson who assumes she’s just a “dumb blonde.” The scene became one of the many iconic moments in the movie. Ariana Grande even recently quoted a later line from the film, in an Instagram teasing the music video for “Thank U, Next.” The video itself pays homage to Legally Blonde and several other much-loved, women-driven films from the turn of the century.
According to McCullah, Legally Blonde went through three drafts before being greenlit. The writing team removed a few R-rated jokes (including one about cunnilingus) so that the movie could hit theaters with a PG-13 rating. When Witherspoon signed on for the role, during the development process, she had her own thoughts on how to tweak the film to make it even more astute. “We had a meeting with her and she gave us really smart, strategic, surgical notes,” Smith remembers. According to Smith, Witherspoon’s notes included a suggestion to better define the characters of Elle’s sorority sisters Margot (Jessica Cauffiel) and Serena (Alanna Ubach).
One of the movie’s most memorable scenes emerged late in the filmmaking process. The “bend and snap” — an exaggerated seduction move in which someone pretends to drop something dramatically and picks it up in a way that emphasizes their body — came about because producer Marc Platt told Smith and McCullah they needed to add a big set piece to the film’s second act. “We racked our brains for maybe a week and a half, going in every different direction,” McCullah said. “We knew it had to be at Paulette’s shop, so we thought maybe it gets robbed or something. Then we thought, well, what if Elle just teaches her a move to get the UPS guy?” The writers were drinking and brainstorming at a bar when they came up with the idea for the scene, and Smith came up with the move on the spot. She later taught the mini dance to famed performer and choreographer Toni Basil, who helped director Robert Luketic incorporate the bend and snap into the film.
Legally Blonde, much like 10 Things, still has a special sheen to it, the kind that only comes from writers with a full command of their craft.
“Luketic decided to turn that into a musical number when we were shooting it, which was quite a surprise to us,” McCullah said. “It was a completely random invention,” Smith noted. “I don’t even know where in my brain and body that came from, but it came out of something.” And, as McCullah added, “it stuck.” In an interview with Entertainment Tonight in 2016, Witherspoon said that she’s frequently asked by fans to perform the move. “I have a feeling I will be doing the bend and snap until I am 95.”
Legally Blonde was a success both critically and at the box office, inspiring two sequels, a Broadway musical, a reality TV show about said musical, and hundreds of thinkpieces. A Legally Blonde rewatch in 2018, much like one for 10 Things, necessitates the acknowledgment that certain cultural norms have changed over the years — most notably a demand for inclusive casting and shifts in the portrayal of LGBT characters. But Legally Blonde, much like 10 Things, still has a special sheen to it, the kind that only comes from writers with a full command of their craft. Legally Blonde remains exquisite and delightful, from Witherspoon’s perky resolve as Elle to the barbed quips Smith and McCullah weaved throughout the film.
One scene, where Elle’s law school teacher Professor Callahan makes a pass at her, has also circled back into public conversation again and again, at once timeless and repeatedly timely. McCullah expressed exasperation at anyone who has the notion that people have only recently started talking about sexual harassment and misconduct. “This didn’t just start, it’s been going on for a while,” she said of the drive behind the #MeToo movement and people sharing stories of men in authority crossing the line. “We were just drawing from real life [with Callahan]. Everyone you know has been sexually harassed by a boss at some point. I don’t think we even had a specific approach in mind, it just felt true, like what we knew to be true.”
In recent years, Smith has noticed that her and McCullah’s work has landed “back on the map” as cultural shifts have caused a push for more films crafted by and for people from marginalized groups. From 10 Things to Ella Enchanted to The House Bunny, every one of Smith and McCullah’s screenplays have incorporated (mostly white) women protagonists and have been geared toward women. “There’s this reignited appetite for the kinds of movies that we want to see, the kind of stories that we were always telling,” Smith said. Their films are what moviegoing audiences in the ’00s called “chick flicks,” though Smith and McCullah are still debating each other over whether or not the phrase has a negative connotation.
“I get asked a lot on panels if I feel like writing chick flicks has put us in a box, but it’s a box I like to play in,” McCullah said. Smith noted that she and McCullah have always been driven to write the types of movies they were craving to see in theaters themselves, “movies about funny, strong, interesting, cool girls.” She added that the pair had lived through an era in which the phrase “chick flick” was used to denigrate any movie that was marketed toward women; McCullah, for her part, responded that she’d never considered the phrase to be a derogatory term at all. “We can’t let those people [using it in a negative way] own it, we need to own the genre. It is a genre,” she said. “There’s a whole genre of [man-centric] movies I don’t like, either.”
"I’m so glad we lasted through the lean years."
When Smith and McCullah started their writing partnership in the late 1990s, “girl power” was the buzzword being thrown around Hollywood as a selling point for any movie featuring a major woman character. “That has now become ‘female empowerment’ and ‘female-driven comedy,’” Smith said, recalling “a dark patch in the 2000s, 2008 to 2012” when the genre she and McCullah had made their careers in largely disappeared. Bridesmaids brought hope for a resurgence in 2011, but Hollywood’s relationship with women-centered comedy has long been a messy one. Smith has hope now, though. “I feel like this whole past year, in particular with stories about women in the headlines, there’s a real hunger for female stories,” she said. “The sandbox is re-expanding again, which is so great. I’m so glad we lasted through the lean years.”
The pair is in the process of returning to their legacy via Legally Blonde 3 (they didn’t write the film’s first sequel, which was not critically well-received but still performed fine at the box office), scheduled to hit theaters in 2020. And as audiences continue to look back on Smith and McCullah’s films, several stand out as case studies of how “chick flicks” — however you think of them — can be gripping, challenging, impressive art that sticks in hearts and minds in big ways.
The pair is far from done churning out pithy, tenacious characters. They’re continuing their writing partnership, and Smith has a Netflix show in the works that will feature a cameo by 10 Things alum Oleynik. But Smith and McCullah’s work is already the stuff of legends. Not many people can say their careers began with two films that remain such prime examples of the craft. ●
The screenwriters of Legally Blonde and 10 Things I Hate About You are Kirsten “Kiwi” Smith and Karen McCullah. A previous version of this article misstated their names in a photo caption.