We’re Not Happy Until You’re Not Happy

Diana Heald reviews Sophie Gilbert’s “Girl on Girl: How Pop Culture Turned a Generation of Women Against Themselves.”

By Diana HealdMay 22, 2025

• Cultural Studies

JESSICA SIMPSON TAKES the stage at a Florida chili cook-off. It’s 2009: Simpson is 29, three years out of her divorce from fellow pop star Nick Lachey. Her career is past its prime, but only just. Though her albums aren’t selling like they used to, Hollywood movies and romantic relationships with singer John Mayer and Dallas Cowboys quarterback Tony Romo keep her name in the press. Simpson’s bouncy blonde curls cascade over a black tank top she’s paired with a wide leopard-print belt and high-waisted dark denim bell-bottoms. If you’re a woman who came of age in the early aughts, you likely already know what comes next. The next day, Page Six will announce, “Jumbo Jessica Simpson: Packin’ on the Pounds.” Other tabloids will call out her “beefy bod,” saying she’s “pack[ing] it in,” “a bigger star than ever.” Sixteen years later, Simpson says she is still traumatized by the damage the media’s fat-shaming did to her self-esteem, and to her career.

And Simpson isn’t the only one: whether they liked her music or not, every one of the female friends I texted about millennial diet culture remembered this moment with precision. The jeans, the belt, the curls, the headlines inscribed in our collective memory, bloating her image into a warning about the value of our bodies. It makes me cringe to reveal the next bit, but because I want you to be horrified, I will: Simpson weighed, at the time, 120 pounds. A trim size four. The coverage would have been cruel and objectifying no matter the size of Simpson’s body; that it was applied to someone so small only further highlights the collective media-induced body dysmorphia that defined the decade. When I look at the images now, I see a healthy, radiant woman, unaware of the poison she’s about to be made to swallow. The rest of us will swallow it too.

This moment in pop culture and countless others like it are the subject of Sophie Gilbert’s sweeping new cultural history, Girl on Girl: How Pop Culture Turned a Generation of Women Against Themselves. Sifting through the wreckage of post-Roe America, Gilbert questions where feminism ran aground, replaced by tradwives who insist that leaving the workforce is a radical act and girlypops who tell their TikTok fans that no one loves women as much as Donald Trump. Gilbert’s expertise as a book and TV critic for The Atlantic gives her a bias toward looking for answers in the music, films, and online videos of the last three decades, playing in the background of a generation of girls.

Gilbert argues that anti-feminist messaging in lowbrow culture is particularly insidious because we consume it as entertainment, without the intellectual rigor we might reserve for art and politics. Of reality TV, she notes that, “because the genre was dismissed as trash—as so many cultural products aimed at women are—few were scrutinizing the values and norms it was atomizing out to millions of female viewers.” Recent memoirs and documentaries have recontextualized the individual narratives of once-maligned famous women such as Britney Spears and Monica Lewinsky, but Gilbert is less concerned with their restitution than with what might be owed to the rest of us. She writes,

I’m interested, too, in what this moment did to those of us who were simply spectators: curious and even envious of the stars whose degradation was offered up to us as thrilling, perpetual, stakes-free entertainment. How did it condition us to see ourselves? And, maybe more crucially, what did it condition us to think about other women and what they might be capable of?

Gilbert traces a careful arc from the sidelining of women in rock and hip-hop in the mid-1990s, replaced by the anodyne “girl power” of the Spice Girls, to the teen sex comedies at the turn of the millennium, the shared obsession with reality TV makeovers in the aughts, and the self-aware hot messes of the 2010s on Girls and Fleabag and in the personal essays of Gawker and xoJane. Along the way, themes recur: a relentless focus on improving and perfecting the body, an erosion of meaningful agency for women, a surveillance culture that teaches them to prioritize performance over fulfillment.

This argument revives the age-old question of whether the media we consume passively reflects our culture or actively shapes it. That media and advertising are simply a mirror of our current cultural values is a favorite argument of the culture creators who insist politics is ruining art and entertainment. But Gilbert’s sustained close reading of the 1999 comedy American Pie is an especially thrilling study of how media shapes us. All I remembered from my single viewing, decades ago, was the sensual encounter between Jason Biggs and the titular apple pie, but Gilbert recognized the origins of incel culture. The main characters’ quest to lose their virginity, “a state that the characters understand as pathetic at best and hierarchically unjust at worst,” renders them involuntarily celibate: “Sex is the goal, virginity the antagonist, and girls the gatekeepers—the ones who are standing in the way of the heroes’ glorious and rightful destiny.” The female characters resist seduction, but the film, Gilbert writes,

offers no insight into why that might be. There’s no sense in the movie that any characters could be stigmatized or shamed for having sex; no fear of teen pregnancy; no shadow of disease or danger. […] in excluding them from its utopian narrative, American Pie makes the decision its female characters are reckoning with into an arbitrary one, which in turn makes it easier to blame them for withholding what the guys want.

Revisiting the case of mass murderer and incel Elliot Rodger, Gilbert considers how his media diet, shaped by his childhood in the shadow of Hollywood and his father’s job as a film director, informed his values. The manifesto Rodger left behind is “strikingly informed by what a lifetime of visual storytelling told him about sex and power,” from his preadolescent exposure to porn to an envy-laced description of the “good looking young people enjoying pleasurable sex lives” (Rodger’s words) in Alpha Dog (2006) to the rampant male cruelty he watched on Game of Thrones (2011–19). “Movies in the aughts hated women,” Gilbert concludes. Rodger believed sex was something he was owed, and he stewed in rage toward the women who kept it from him. It’s hard not to see echoes of those same views in the film and TV he grew up watching.

Gilbert’s narrative culminates in the 2008 financial crisis–induced hustle culture encapsulated in the rise of the “girlboss” and in Sheryl Sandberg’s 2013 book Lean In: Women, Work, and the Will to Lead. Media in this era positioned the individual success of a handful of telegenic, mostly white, venture capital–backed female founders—Emily Weiss of Glossier, Sophia Amoruso of Nasty Gal, Audrey Gelman of The Wing—as a triumph for all women. Gilbert identifies “an undercurrent of scamminess to the girlboss era.” Supporting their companies, says Gilbert’s Atlantic colleague Amanda Mull, meant that “maybe the patriarchy was just a choice that savvy consumers could shop their way around. Maybe people could vote for equality by buying a particular set of luggage or joining a particular co-working space.” If the riot grrrls and female hip-hop stars of the early 1990s offered radical forms of resistance to patriarchy, the girlboss represented the apotheosis of “trickle-down feminism,” redirecting solidarity toward individual success. When complaints about racism, bullying, and bad business practices among female founders reached critical mass, Gilbert writes, the public realized that “many girlbosses operated just like men—they weren’t interested in the elevation of other women at all.”

What’s left of feminism in the post-girlboss, post–Me Too, post–Roe v. Wade age is even harder to identify. A partial list of media topics I’ve consumed in the last half-year: GLP-1 inhibitors erode paltry gains made by the 2010s body positivity movement; Vice President J. D. Vance questions whether women without children should be allowed to vote; the pronatalists “want women to start having a lot more babies,” as if the role played by men in falling birth rates is incidental; “Your body, my choice” trends on social media in the days after Trump’s election. The headlines keep rolling in, the way they have all my life, faster than I can absorb their implications.

Gilbert concludes Girl on Girl on a positive note, buoyed by the power she sees in women like Simpson and Spears telling their stories, but on most days, I find her optimism hard to share. Like many millennials, I was raised on the MLK chestnut that “the arc of the moral universe is long, but it bends toward justice”—two steps forward and one step back is still progress, after all. But the bulk of Gilbert’s research illustrates another pattern, less arc than cycle, in which each challenge to the status quo is met with thundering resistance. Still, I’m reminded that to identify a pattern is the first step toward breaking it, or as Adrienne Rich wrote, quoted in Girl on Girl’s introduction, “Until we can understand the assumptions in which we are drenched we cannot know ourselves.”

Girl on Girl is more interested in illustrating the sources of misogyny in pop culture than in exploring their tangible effects, mostly eschewing its personal impact on Gilbert. She writes, “I wanted […] to expand the ways in which I understand and think about this era, and inserting myself into it only ever seemed to be inhibiting my scope of vision.” But her approach has given me new tools to examine incidents from my own life, from how I internalized pop culture to more personal run-ins with misogyny—the leering gaze of high school boys, the way we used to be proud to say we didn’t like books and music made by women, the girl I grew up with who got kicked out of school after her boyfriend secretly filmed them having sex and played the video for our driver’s ed class. There was a lesson in each of these episodes for us girls, but as with so many of the messages we received about our bodies, our sexuality, our abilities, I could never quite articulate what it was. Reading Girl on Girl, I located it in the words of adult filmmaker Max Hardcore, whose simulated rape films Gilbert calls “psychodramas of rage directed at feminine beauty.” Introducing an aspiring porn actress to his practice, Hardcore says, “We have a saying around here. […] We’re not happy until you’re not happy.”

I suspect many millennial women have memories like these. Sophie Gilbert is determined to surface them, to see the ample historical precedent for our current moment in all its horror. Girl on Girl is hard to read—I found the onslaught of toxic messages enraging on my first pass, back in December, and nauseating on the second, a few weeks ago. In the intervening months, self-proclaimed misogynist Andrew Tate had returned to Florida despite rape and human-trafficking charges against him, feeling newly comfortable in Trump’s America. Encountering his name in Girl on Girl, I had to put the book down to cry. But it also led me to pick up my phone, again and again, to text old friends. “Remember this?” I’d ask, sharing a picture of Jessica Simpson in her high-waisted jeans. Everyone did—and as we reminisced, all of us nearing 40, it seemed like we were finally ready to be angry about it.