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On HBO Max series Hacks (streaming on Crave in Canada), Jean Smart (right) plays comedian and demanding boss Deborah Vance opposite Hannah Einbinder.Courtesy of HBO Max

Ask anyone to name a female boss in pop culture and it’s likely one character will be on everyone’s list: Miranda Priestly, the Anna Wintour clone who makes Andy Sachs’ life miserable as the editor-in-chief of the fictional Runway magazine.

It’s been 15 years since The Devil Wears Prada was released, but Priestly has become iconic in the pantheon of pop culture bosses – for all the wrong reasons. In the early 2000s classic, her character is clearly meant to be the villain; she deliberately pits employees against one another, expects them to work to the point of burnout and is a master of the cutting jibe. Priestly exemplifies every stereotype of the bad female boss, a trope that’s so well established in TV, movies and, unfortunately, real life that googling the term returns 196 million results.

But what’s most interesting about Priestly is the way we’ve related to her as time has passed. By the mid- to late-2010s, we had entered the era of the girlboss, when women’s professional success and financial gain became synonymous with feminism, a kind of “trickle down” social justice that was never as empowering as Sheryl Sandberg and her contemporaries would have us believe.

At the same time, TV was brimming with female anti-heroes, including Veep’s Selina Meyer, Scandal’s Olivia Pope, How to Get Away with Murder’s Annaliese Keating and House of Cards’ Claire Underwood. Arguably, all of these women were terrible bosses, but by this point it was a less a lazy stereotype and more an opportunity to explore how power works.

It’s in this context that cultural critics began rethinking Priestly’s cruelty. “It’s absolutely true that Miranda Priestley seems like a dreadful employer,” wrote Washington Post columnist Alyssa Rosenberg at the time. “[But] if Miranda were a man, she might be the hero at the end of The Devil Wears Prada, the character who sees the greatness in Andy and pushes her to achieve it. Instead, her role in the movie is more ambiguous. She becomes the person against whom Andy defines herself, the avatar of everything Andy doesn’t want to be, who nonetheless gives Andy the reference that helps her pursue a career as a reporter.”

Now, against the backdrop of a pandemic, a “racial reckoning” and the so-called great resignation, where workers are leaving their jobs in pursuit of more fulfilling opportunities and/or better work-life balance, the way we relate to Priestly and other fictional female bosses feels even more complicated. For starters, not very much has actually changed.

“The women we see as bosses on TV often mirror the structural issues [faced by] women seeking positions of leadership in real life,” says writer, editor and cultural critic Ishani Nath. These issues include the “overrepresentation of white women, Black women having to start their own thing in order to be at the top, few Asian women, no Indigenous representation.”

Ms. Nath notes that there’s also a dichotomy of women bosses on TV who are either “struggling to balance work and home life or women who are hardened and choosing to live alone – [neither] of which are narratives that apply to male bosses.”

She’s not wrong. While there are some pretty good female bosses on TV right now – qualified, level-headed Gerri Kellman from Succession comes to mind (leaving aside the current situation with Roman Roy), as does Liz Lawrence on The Good Fight, who is both respected by her employees and granted a life outside of work – even they are subject to questions about complicity and the evils of capitalism.

What’s more, many of the female bosses on television right now are cast from the same mould as Miranda Priestly. Hacks’ Deborah Vance and Ted Lasso’s Rebecca Welton may benefit from more character development than their predecessor, but they still tick off many of the same stereotypical boxes: blonde, white, ball-busting, selfish, lonely in their personal lives.

There are more racialized bosses on screen now, which is a win for representation, but they’re not immune from these “career woman” tropes, either. Regina from Maid is depicted as overly demanding and emotionally stunted. Even The Chair’s Ji-Yoon Kim, who is in many ways ultraprogressive, has a messy personal life.

“Perhaps the issue is that we haven’t seen any new types of bosses because our structures [in real life] have yet to change,” says Ms. Nath. “Pop culture can be a way for us to imagine what’s possible, but we still don’t even know what that looks like for women in the work force.”

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