Harvey Weinstein's former personal assistant writes tell-all play (sorta)

Leslye Headland loves Harvey Weinstein—despite having worked as his personal assistant. And he most likely loves her back—even after she penned the play Assistance,about ill-treated young personal assistants at a fictional corporation called the Weisinger Company headed by a demanding, impatient, perfectionist named Daniel Weisinger. At the very least, the Oscar-courting head of The Weinstein Company isn’t holding a grudge against Headland. The indie studio recently purchased her much-loved comedy Bachelorette (which she wrote and directed, based on her own play) at this year’s Sundance Film Festival.

The 31-year-old NYU graduate insists that Assistance, which opens tonight Off Broadway at Playwright’s Horizons, is not a tell-all about her former boss, as much as it’s an exploration into the minds of executive assistants — in this case jaded veteran Nick (Michael Esper), kind newbie Nora (Virginia Kull), scatterbrain Heather (Sue Jean Kim), masochist Justin (Bobby Steggert), and cool-as-ice Jenny (Amy Rosoff). The play asks why they do what they do, and why they often do it for so long (Headland herself worked at Miramax and the Weinstein Company for six years). But just try watching a play in which one downtrodden assistant is shoved out of a gypsy cab — and then run over by the same cab — and not think of the notoriously temperamental Weinstein. So we spoke with Headland to see if she’d set the record straight.

ENTERTAINMENT WEEKLY: You must have known that because of your connection to Miramax and the Weinstein Company, people assume Assistance is about Harvey Weinstein. Didn’t that scare you?

LESLYE HEADLAND: The thing is, the play is so much not about the boss. And when I was an assistant, I worked for a lot of different people. I worked for the copresident of production at Miramax. I work for Harvey for about a year, and then I worked for Arianna Huffington for about a month. It was a job I did for a while. So, it wasn’t like I came into contact with one person and was like, “Oh gosh, he or she would make a good story,” as much as it was like, ‘Wow, why was I an assistant for six years?’

It did seem that you were criticizing the assistants for getting stuck in the cycle of abuse more than their boss for inflicting it.

Yeah, it’s more about the assistants than the boss—which is the No. 1 thing that separates it from the tell-all culture of an assistant’s memoir.

So, it’s the exact opposite of The Devil Wears Prada…

Yeah. I never read the book, but movie is pretty good. Although, I was an assistant at the time and while watching it I was thinking, “This is really stressful.” I was also like, “I could’ve gotten [Meryl Streep’s character] out of that situation.” I was like, “You can get her out of there in the middle of a hurricane. You just have to work harder!” That’s what I mean: It’s that mentality that is more interesting to me than what is the most outlandish thing a boss can ask for.

Did you start writing the play while you were still working at the Weinstein Company?

Way after. Harvey knew that I was a writer. People I worked with knew I was a writer and they would speculate, “I bet you’re going to write about us some day.” And, I was like, “No, it’s not that interesting of a world.” As far as it being autobiographical, none of that stuff ever happened. I’m so not afraid of it because it’s not true. It’s all stuff that I made up and thought would be funny. Actually working for Harvey was very educational and cool, but it was pretty boring.

Did you base any of the assistants in the show on people you knew?

They’re based on different versions of myself throughout the job. Nora is how I would like to see myself. I felt like Justin at times, looking past whatever was going on with me personally in order to get back to the job. I’ve definitely neglected my own health in order to get to work. But I was more like Heather as an assistant, to be honest. I felt overwhelmed a lot and I couldn’t figure out how to complete simple tasks. I felt like I was stuck in the same routine and there was all this work being done but I wasn’t really accomplishing anything.

What goals weren’t you achieving?

That was one of the problems. I didn’t really have any. I thought I would learn a lot, which I did, and then I was just staying because I was afraid to become a writer. Harvey was one of the few people who was supportive. He was like, “You’re a good writer, that’s probably what you should do.”

You call Assistance’s fictional business the Weisinger Company, but you never make it clear that the characters work in the film industry — or any industry, for that matter.

If you name what industry they’re in, like the film industry, [people have preconceived notions that] making movies is a really cool industry. In this particular story, it’s really important that they’re not making anything and that no one is skilled at anything. I made the direct choice to not only not show what they did, but also for the assistants to not necessarily be the good guys — like in the ways they’re failing at their jobs and all they’re really getting good at is helping this one person.

So do you get the sense that kids graduating from college these days now simply expect to be treated horribly at their first jobs — that they seem to naturally accept the Swimming With Sharks or Horrible Bosses lifestyle?

That it’s a cultural thing now? Absolutely. It’s something I’m very interested in as a playwright. I like going toward stories that people already know the setup of and then asking different questions. Like, if you’re leaving school and you’re expecting to be treated horribly, one of the things that this play asks is: Why? What do you think about your self? Nick and Nora’s fatal flaw is that they think that it’s just being around this guy that’s going get them what they want as opposed to going out and getting it themselves and that’s because the alternative is really hard and really scary.

What was your feeling, then, when you found out that The Weinstein Company had bought Bachelorette?

It was so funny and great. When I was working there, that was all I wanted — I would daydream that someday I’ll be making movies and Harvey will buy them and, and he will want to support me. You know, as coworkers essentially. There’s nobody like him. He’s genius. You sit across from him and you’re like, “I cannot believe how brilliant this guy is.” So his interest in me as a filmmaker just makes me feel like I made the right choice to move on.