Oliver got her start as far away from Hollywood — she grew up in South Carolina and attended Stanford as an undergraduate. Her career kicked off with directing and acting gigs before she found her way to screenwriting (she appeared alongside Little star Issa Rae in The Misadventures of Awkward Black Girl) but as soon as she began writing for the screen it became apparent that she was uniquely fit to change the business altogether.
“What I started learning about the business part of the industry is that writers create all the intellectual property,” she explained to EW at the offices of her publicity firm. “There’s nothing unless you get the script right, but then once it’s cast you don’t participate in that script’s success.”
That is a revelation that has come, often painfully, to many writers in Hollywood, but Oliver decided to take an active role in changing the system. She realized that if she was going to keep saying yes to the increasing requests to work on more and more scripts she had to get more out of it.
“I’m part of what I hope is a new movement of people who are demanding, if you want my ideas and my work, I have to have equity in it like you do,” said Oliver. “I’m not saying we can’t share in it or that I have to have it all, but I want to participate.”
In the case of projects like the upcoming The Sun Is Also a Star, that means demanding an executive producer credit — and it also means being okay with walking away from a project if the studio isn’t willing to say yes. The first time Oliver put her philosophy into practice she was turned down, and while she was making calls to her team questioning whether she should have folded, the studio came back to accept her demands, validating her opinion that screenwriters deserve more.
“Writing is the hardest part of entertainment,” she said. “I say that because I directed and acted for years and nothing gives me a migraine like sitting down in front of a blank screen when you have to create an entire world from scratch.”
With Little, which hits theaters today, that brainstorming process went differently — star Marsai Martin, best known as one of the Johnson children on Black-ish, was looking to pitch a movie and brought her idea of reinventing Big to Black-ish creator Kenya Barris and Oliver. She was 10 years old at the time (let that sink in), and Oliver left the meeting sufficiently impressed and fleshed out their ideas into a formal script pitch to take to Universal.
“She had some notes and some jokes that she wanted to include,” Oliver said with a smile. “We did that whole bit with spanking from the trailer. In the pitch she was way more confident than I was — she was telling me to pull it together. And they [Universal] bought it in the room.”
The flick, which is kind of Big meets 17 Again meets 13 Going on 30, follows Regina Hall’s Jordan, the successful owner of an app development firm who also happens to be a huge bully. She wakes up one morning as her childhood self (played by Martin) and is forced to reckon with the person she’s become. But, like, it’s funny. (This is the writer of Girl’s Trip after all).
The plot pulls inspiration from Oliver’s Stanford days (where she was surrounded, quite literally, by the Elizabeth Holmes’ of the world) and also from her own relationships with less-than-nice bosses — played out onscreen by Issa Rae as Hall’s (slash Martin’s) assistant.
“The movie is kind of a fantasy because they have to have this relationship in which April is able to say all the things you wish you could tell your boss,” she said. “But the good thing about movies is that characters have to change.”
Little has a PG-13 rating and a 14-year-old star, which presents a unique challenge for a comedy writer who’s used to pushing the boundaries. Oliver worked hard to balance the need for irreverence with the need for age-appropriate jokes — a scene with the young Jordan smoking weed became a scene about wine-drinking, and she admitted there was plenty of discussion about a (hilarious) back-and-forth between young Jordan and her incredibly hot teacher (played by an incredibly good-natured Justin Hartley). It was a stark contrast to Girls Trip when Oliver found herself as chief sensor for the first (and probably last) time.
Oliver normally writes her jokes as boundary-pushing as possible, and then reels them back as the studio suggests, but she found the Universal team asking for even more raunch on the Girls Trip script: That process brought audiences the grapefruit scene and that now-infamous image of Jada Pinkett-Smith peeing over a crowd on Bourbon Street.
“It made me nervous,” Oliver admitted. “Black women had never been seen in that way before. We weren’t allowed to be that raunchy, we weren’t supposed to do that onscreen for whatever reason. So it fed into my fear that I was going to get, like, an open letter about representation. I was like, I don’t want this, I just want to make a fun movie and not the pressure of it saying more than what it is.”
Which is exactly what she continues to do. After Little, she’s working on the upcoming adaptation of YA novel The Sun Is Also a Star, as well as the remakes of First Wives Club and Clueless. In addition to creating female characters who represent real women — she noted that she continues to remind studio executives that not every female story needs a love story — she’s hell-bent on handing out Hollywood opportunities as judiciously as possible.
“Just a few years ago when I was starting out there were so few black women screenwriters, so I didn’t really have anybody to reach out to,” she explained. “I didn’t have this community of women to reach out to and it was really hard and frustrating.”
She has now made mentorship a priority in her life and also spends extra time to discover new talent — if she’s offered a screenwriting gig that she’s unable to accept, or on projects she is producing, she makes sure to hire someone who wouldn’t have that opportunity otherwise. On the upcoming Clueless remake, she fought hard to bring on a black female writer who was having a hard time getting hired on a studio film because she’d never done one before. For the remake of First Wives Club, a friend sent her a script by a woman living in Philadelphia that Oliver described as “f-king hilarious” but who had never staffed on a series. She advocated to bring her to Los Angeles, and now that writer has an agent and has sold her own project.
Oliver describes her mentoring as a twofold process — vouching for new talent and then getting hands-on to ensure their success once they’re hired: “I’m doing the mentoring and the advocating that I wish I had.”