Mindy Kaling's 'Late Night' and a twist on Hollywood's bad female bosses

But as these stories subvert old stereotypes, they construct new ones. Often the implication is that these women are bad because they are older. Their internalized sexism is framed as a generational problem. They are cast as products of their time — a bygone era during which the few women allowed to infiltrate the boy’s club were the ones seemingly willing to betray, ignore or punish other women. The culture at large is also interested in maligning and discarding women of a certain age — Katherine jokes about it often in “Late Night” — so it is a little bit uncomfortable that these stories so often locate feminist potential in young women. These more enlightened women of a younger generation, unlike their compromised leaders, are apparently so self-actualized that they are capable of being successful and sisterly at once.

In “Late Night,” this archetype takes the form of Molly, who is as nice as she is competent: She arrives at work with lots of ideas, and also cupcakes. By film’s end, she has shown her boss the error of her ways, saved the show and forged intergenerational unity between women. The construction is deployed quite literally in “Little,” where Jordan Sanders, the tech mogul played by Regina Hall, gleefully crushes her assistant (Issa Rae) beneath her heel. Jordan realizes that her abusive actions are rooted in fear of other women only after she is transformed into the body of her younger self.

And it is savagely satirized on “Veep,” when Selina (Julia Louis-Dreyfus) squares off against a younger female rival for the presidency, the lawyer-turned-Sen. Kemi Talbot (Toks Olagundoye). When Kemi repeatedly identifies “as a woman, and a woman of color” on the debate stage, Selina counters that when she entered politics, she was forced to endure discrimination and harassment without making a fuss, and she advises the young women of America to “stop complaining and man up.” Because in “Veep,” the worst people always win, “Man Up” becomes Meyer’s triumphant campaign slogan.

The big, bad powerful woman is a news fixture, too, and accounts of real-life women are in close conversation with fictionalized ones. Sheryl Sandberg, the chief operating officer of Facebook and founder of Lean In, was hailed as a mentorship icon until revelations about her role in the platform’s political disinformation crisis cut her down to size. A memorable “Veep” joke — that Selina once forced an aide to “dry shave” her legs under a conference table — was inspired by a rumor about Sen. Amy Klobuchar that ricocheted around the capital. (A representative for Klobuchar said it never happened.) When Klobuchar announced her bid for the presidency, she set off furious debate as to whether she is a nightmare manager, or she is simply being held to a higher standard because she is a woman. Two feminist impulses are in conflict here: It’s not always possible to defend a female boss’s reputation from attack while also protecting female employees from a self-interested employer.

Generational conflict is etched into the story of American feminism. The social movement is chopped into waves, which can give the impression that a feminist’s beliefs and loyalties may be divined by her date of birth. The stories we tell about feminism are often mapped onto the relationships between mothers and daughters, or else between employers and employees. These tales tend to cut two ways.

One narrative pitches older feminists as the real activists who fought hard for rights that younger women now have the luxury of taking for granted. That’s the undercurrent to the second season of “The Handmaid’s Tale,” in which flashbacks show June’s activist mother volunteering as an abortion clinic escort while June is complacent with her fiancée and her publishing job — leaving her shocked when the misogyny pulsing beneath polite society explodes into overt subjugation of women.

But a more fashionable narrative, these days, argues that feminism grows naturally and inevitably over time, leaving each new generation of women more equipped to live out feminist principles than the one that came before. That idea animates the almost-one-woman-show “What the Constitution Means to Me,” in which Heidi Schreck, a former teenage competitive debater turned writer and actress, tells the story of how several generations of women in her family dealt with male violence and control, with each one becoming increasingly awake to her own power.

The play takes the form of a faux-teenage constitutional debate, and just as Supreme Court Justice William O. Douglas used the metaphor of a penumbra — the partial shadow between the darkness and the light — to extend an implied right to privacy in the Constitution, Schreck uses it to argue that the history of women in the United States is a slow but inevitable movement toward freedom and enlightenment. Near the end of the show, Schreck pitches the idea forward, bringing a current high school student onstage — a role played on alternating nights by Thursday Williams and Rosdely Ciprian — to debate her, and also to represent the bright future of feminism. “I have learned so much from younger women, from younger feminists,” Schreck says. “Sometimes, I feel like you are shining a light backwards into the darkness so the rest of us can follow you into the future.”

A similar dynamic is explored less optimistically in Meg Wolitzer’s 2018 novel “The Female Persuasion.” A famous second-wave feminist activist and speaker, Faith Frank, partners with a venture capital fund to create a feminist foundation, only to be shown up by her mentee, the millennial Greer Kadetsky, who deserts Frank when she realizes that her wealthy investors are not, ultimately, allied with the movement. This is a little disingenuous; if any generation has seamlessly aligned feminism with capitalism, it is Greer’s. But the book’s meditation on intergenerational relationships between women — how mentorship is tied up with competition, and how discarding existing leaders is necessary to make room for new ones — feels honest, even if its constructions are pat. By the end, Greer has written a best-selling feminist self-help guide, and now it is her turn to be eyed as out-of-touch. The message comes from her teenage babysitter, Kay Chung, who informs her that younger women do not “care about figureheads.” They are only interested in dismantling structures.

One of the most interesting things about the bad boss archetype is her ability to shine a light on those structures. She is evidence that the patriarchy is not simply propped up by men; it colonizes everyone it can. By its seventh and final season, “Veep” had become a lame-duck satire, but the series finale was oddly moving, in part because it offered a sincere explanation for why Selina is the way that she is. In the midst of one of her many bids for the presidency, a male rival tells her: “You don’t have a political future, Selina. That is your punishment … The party and the nation will never forget all that door you pushed open.” But instead of giving up, Selina goes on a political rampage, proves herself more ruthless than even the men, and finally wins.

The message is that progress develops too slowly to benefit the women who pushed for it. Selina always had to fight harder to survive; she had to sacrifice everything, including her friends, her family and her conscience. Younger female candidates like Kemi might have the luxury of being powerful and liked at the same time: At the series’ end, we learn that Kemi went on to become the first woman to serve two full terms.

But history does not always unfold so neatly, with youth and progress handsomely paired. In her Netflix stand-up special, “Growing,” Amy Schumer makes a warm joke about the newly enlightened culture around sexual harassment. Pitching herself as a woman from an older generation, she says: “I’m so grateful to this new generation of women that came along, and they’re like, ‘Hey, have you been getting sexually harassed like this your whole lives?’ And we’re like, ‘Oh … yeah!’”

The joke is that the young women have the perspective to demand progress on problems that older women had to simply endure. It’s a nice idea, but a false one. The women who led that change — among them, the 45-year-old #MeToo creator Tarana Burke and the 51-year-old actress Ashley Judd — are older than Schumer, who is 38.

The truth is this: Feminist attitudes do not split cleanly on generational lines. The vast majority of older women are socially and politically powerless. And progress is often interrupted by setbacks and backlashes. But age can be a tempting metaphor. If younger women do have some kind of moral advantage over older ones, it is not derived from their youth or determined by when they were born. It comes from the fact that they are simply not old enough to have amassed great corporate or political influence, or to have had the chance to be corrupted by it. They may be at the bottom of the career ladder, but they retain the moral high ground.

Increasingly, race is deployed this way, too. Often in these stories, the older feminist is a white woman and the younger one is a woman of color — as are Thursday and Rosdely of “What the Constitution Means to Me,” Molly of “Late Night,” Kay of “The Female Persuasion” and Kemi on “Veep,” who is a kind of avatar for Kamala Harris. This helps to poke at the idea that powerful women are not only evidence of feminist progress. They are also agents of traditional hierarchies — racial, political and corporate — which they work to maintain.

But there is sometimes a touch of condescension to these depictions, too, as if young women of color are naturally imbued with moral righteousness. These women risk being drawn more as symbols than as people. One of the sharpest lines in “What the Constitution Means to Me” comes when Schreck praises Thursday in the course of their debate, saying that she’s ready to knock on doors for her congressional run, and Thursday raises an objection: “Pandering!”

It is probably not a coincidence that the role of the powerful woman tends to be deliciously complex while that of the up-and-comer is comparatively thin. The bad boss, whether in business or politics, is jumping with social tensions. Executives and senators are curious avatars for feminism, after all: Feminism is a movement bent toward equality, while power necessarily accrues to a select few. Often, powerful women are upheld as agents of feminist change when all they have changed are their own circumstances. Efforts to insist that such power “trickles down” are not incredibly convincing; millions of women are left competing for droplets.

And yet this woman’s power is precarious. She is always at risk of losing it, especially as she grows older. The very insistence that powerful women necessarily be feminists can precipitate their fall. It becomes another instance of setting the bar higher for women than it is for men. If women wish to seize power, they must compete ruthlessly with one another, but if they want to be seen as good feminists, they must act as if they are not in competition at all. They must promote a fantasy that they have succeeded virtuously. Men are not required to do the same.

The ruthlessly competent ladyboss gets a bad rap. But perhaps the more troublesome archetype is that of the bright young woman who rises to power without compromising her values at all. She makes it seem as if all of the problems of power can be neatly resolved by one plucky individual. She suggests that society really can change for the better, as soon as a better woman comes along. Especially if she brings cupcakes.