terrible bosses

Harvey Weinstein and Hollywood Bosses From Hell

Photo-Illustration: Marcus Peabody/Getty Images

What makes a boss truly terrible — and how do you deal with it? Vulture film critic Alison Willmore writes about Weinstein and #PayUpHollywood as part of a weeklong series about what makes a bad boss, and why we’re so tortured by them.

Leslye Headland wrote a play about working for Harvey Weinstein back in 2008. It was an experience she knew something about. Headland, the filmmaker and co-creator of Russian Doll, spent six years as an assistant at Miramax and the Weinstein Company, one of them reporting directly to Weinstein himself. Assistance wasn’t about the accusations of sexual assault and harassment that would begin emerging and accruing almost a decade later, the ones that would (maybe) put an end to his career and result in his being charged with rape. Aside from a few faint hints on the margins, Assistance wasn’t about sexual abuse at all.

Weinstein was notorious for being a monster long before he became synonymous with the surge of the Me Too era, but it was a “That’s showbiz, kid!” sort of notoriety. Over the four decades of his time in the business, articles and books like Peter Biskind’s Down and Dirty Pictures would recount his nightmare-boss antics as gossip or a sidebar to industry news. Like the time he reportedly decided that an intern would henceforth be known as “Fuckface,” or that habit he had of firing people, for real or for show, on the spot when displeased, or the incident in which he hurled a framed photograph across a room, or his repeated, legendary public meltdowns at his staff when things didn’t go his way. It was the kind of behavior you can only really get away with in public when you’re powerful, but that also, perversely, can be used to underscore just how powerful someone is. It’s a kind of behavior that assistants can bear the brunt of, which is why complaints about it resonate with the recent groundswell of #PayUpHollywood, a movement made up of assistants who’ve been rallying together for better pay, hours, and working conditions. It isn’t part of Me Too, exactly, but it’s clearly inspired and empowered by it, evidence that there are ways of contending with abusive behavior that falls outside what’s plainly illegal.

Daniel Weisinger, the Harvey Weinstein stand-in in Assistance, never makes an appearance onstage, though he looms threateningly over the entire production. (Nor, for that matter, is it ever made explicit what industry he works in. It’s just clear that it’s a high-status one.) It’s a choice Headland was criticized for when the play opened Off Broadway in 2012. “After a while it’s like watching The Devil Wears Prada with the Anna Wintour character snipped from every scene,” Charles Isherwood wrote in his review in the New York Times. But, of course, Wintour was the real, delicious focus of The Devil Wears Prada, whereas it’s not Weinstein that Assistance is actually about. The play explores the psychology of the people who’ve shaped themselves around him, who’ve learned to accommodate his capriciousness and his rages, and who’ve accepted it as a nightmarish sort of normalcy. As Headland told Vulture in February, “I think what was interesting was looking at how abuse cycles and trickles down throughout a culture and a company.”

And work is noticeably, for the characters in Assistance, an ongoing abusive relationship. They constantly try to rationalize the things they’re subjected to — the lousy pay, all-consuming hours, unreasonable demands, and screaming fits — as they white-knuckle their way through with the promise of promotions that seem almost mythological. They sometimes vent, or try to protect each other from their employer’s wrath, but more often they accept it as their due. As a character says at one point, “I don’t need another person telling me Daniel Weisinger is an asshole. If he acted like everyone else, he’d be everyone else. He’d be a nobody.” He delivers this line while sporting a cast because after he was fired and ordered out of the car he and his boss were riding in, the car ran over his foot. He later took the job back, and is insisting to his therapist that he’s the one who was at fault: “I was standing too close to the car.”

It’s a Stockholm syndrome–y sequence that recalls an anecdote from Vanity Fair’s 2011 profile, in which Weinstein apologized for being an asshole on set, and someone responded, “Yeah, but you’re our asshole, and we’re glad you’re back.” Or the way that Weinstein’s brother and business partner, Bob (infamous in his own right), talking to The Hollywood Reporter in October 2017, said that he didn’t do anything after his sibling “got physical” and assaulted him: “It doesn’t absolve me of my own cowardice, but this is the thing that happens.” Getting your foot run over by your boss, as the Weinstein equivalent does in the play, or having a lit cigarette hurled at you, something the real Weinstein reportedly did to then–acquisitions executive Jason Blum, are the kind of things that get treated as war stories, presuming one can weather them, because they’re signs of the kind of monster a powerful person is allowed to be. Or, in some dark ways, expected to be, as though kindness is a weakness and being respectful to people around you is a burden that can be relinquished once someone is important enough.

There are so many different breeds of terrible boss in the world, but there’s something about Weinstein’s particular brand of toxicity, his temper and streak of sadism, that seems particularly central to the film industry. When there’s no obvious path to move up the ladder in an increasingly capricious business, the ability to endure a gauntlet of pettiness and pain can seem like the way of paying dues. And that means that when someone does ascend, they might just feel emboldened to return the favor to those aspirants below them.

Isherwood compared Assistance to The Devil Wears Prada, but the truth is that the Hollywood answer to The Devil Wears Prada came out long before then, a 1994 indie called Swimming With Sharks that was about a fresh-faced young graduate and the vicious executive he ended up working for in what he thought would be a dream job…until he snaps and takes his boss hostage at gunpoint. When it came out, people couldn’t agree on who the mogul was inspired by — whether it was Barry Josephson, or Scott Rudin, or Joel Silver — because there were just too many possibilities. Weinstein is far from the only Hollywood bully. He was just the most prominent example to flame out so spectacularly that people outside the industry took notice — part of a tradition of toxicity as old as Hollywood.

Bullies are a dime a dozen, and Headland is right that the more interesting subjects are the people around them: the people who learn to weather their tirades or submit to their whims, all the while hoping that it will pay off for them in the end, and the people who realize that they’re not going to actually get what they want, no matter how much they put up with. And you can add to that pile the people who start to push back, like the assistants of #PayUpHollywood, and reject the assumption that abjection is the only way to earn a spot in the industry. It’s a reminder, also, that the dichotomy that’s so often presented with these jobs, one of enduring or giving up, doesn’t have to be a true one, and that there’s more to work than the ability to withstand punishment.

Harvey Weinstein and Hollywood Bosses From Hell