At the start of 1999, Jennifer Aniston was 29 years old and probably the most bankable star on definitely the biggest TV show in the world. NBC’s Thursday night “Must See TV” lineup (which included, at various times, Seinfeld, ER, and 3rd Rock from the Sun) had pushed the network back to primetime-TV dominance, and Friends was the jewel in that crown.

The show launched in 1994, explicitly to reach the rising market of Gen X–ers starting out on adult life in the big cities. And how better to find that audience than by putting it on-screen?

Jerry Seinfeld considered Friends’s basic elements—a sitcom about a group of singles in New York City—to constitute a do-over of his own show with a better-looking cast. But Friends was more than Seinfeld with beautiful people. In contrast to Seinfeld’s self-imposed “no hugging, no learning” rule, part of the point of Friends was that you got to see its characters grow and change over time, blurring the line between sitcom and soap opera.

The six main characters on the show seemed like people you would actually be friends with. “I remember when I was a young person watching Friends, I thought, ‘This is how we talk,’” said Sean Hayes, who went on to play the character Jack in another Must See TV mainstay, Will & Grace.

Aniston’s character, Rachel Greene, was the one who had the most growing and changing to do, so it made sense that audiences would become particularly attached to her. She’s the last of the six to show up in the pilot episode, crashing into the coffee shop, where the others are gathered, dressed in a bridal gown, on the run from her own wedding. “I just had to get out of there,” Rachel cries as she explains her situation. “I started wondering, ‘Why am I doing this and who am I doing it for?’”

It’s a smart upending of the typical rom-com plot: Rachel’s story doesn’t end when she gets to the altar but, rather, begins when she realizes the man at the altar is entirely wrong for her. It was also a reflection of American lives in the 1990s, albeit a melodramatic one. In common with people of all developed nations, Americans were getting married later, or not getting married at all, and the driving force of that trend was a generation of educated, ambitious young women for whom husbands and babies would come, if they came at all, after career and self-discovery.

From Season One of Friends: “The One Where Monica Gets a Roommate.”

By 1999, Rachel had been transformed from a princess reliant on her daddy’s money into a capable young woman with a career in fashion—and a tantalizing on-again, off-again relationship with Ross, played by David Schwimmer. She was the perfect example of the independent young woman making her way, and plenty of women chose to model themselves after her: the layered, face-framing hairstyle Jen wore on the show became a phenomenon in its own right, as millions of women went to their salons and requested “the Rachel.”

Aniston was valuable, and along with the rest of the Friends cast, she knew it. The six of them—three men, three women—formed what Schwimmer described as a “mini-union” and negotiated a deal that not only placed them among the best-paid actors on TV, but also gave them syndication royalties. Aniston had kicked against the glass ceiling, helping to create a micro-economy for herself and her co-stars with a perfect gender balance and no wage gap at all.

Americans were getting married later, or not getting married at all, and the driving force of that trend was a generation of educated, ambitious young women for whom husbands and babies would come, if they came at all, after career and self-discovery.

Her professional life was more or less a self-made Utopia. This success made her an object of admiration, but it also put her at the center of an existential panic over women’s choices in the aughts.

Friends made that panic part of its drama. Like the women who saw themselves in her, Rachel Greene was dealing with new dilemmas thrown up by the modern schedule for living. Deferring settling down brought choices and freedoms, but you still couldn’t barter away the limits of the female body. Fertility remained finite. In the 2001 Friends episode “The One Where They All Turn Thirty,” Rachel goes through a landmark birthday—and becomes upset when she realizes how far behind her “plan” she actually is:

See, I wanna have three kids … I should probably have the first of the three kids by the time I’m 35, which gives me five years. So if I wanna have a kid when I’m 35, I don’t have to get pregnant until I’m 34, which gives Prada four years to start making maternity clothes. Wait, but I do want to be married for a year before I get pregnant … So I don’t have to get married until I’m 33. That’s three years. That’s three whole years. Oh, wait a minute though, I’ll need a year and a half to plan the wedding. And I’d like to know the guy for like a year, year and a half before we get engaged, which means I need to meet the guy by the time I’m 30 … According to my plan, I should already be with the guy that I’m gonna marry.

For the young women watching, Rachel’s distress was relatable: many would have their own plan, or at least be aware that such choices would be forced on them at some point. But in the culture at large, one of the aughts’ prevailing anxieties about women was that they were being altogether careless about their plan, complacently wasting their prime reproductive years in pursuit of education or professional advancement.

From Season Five: “The One Where They All Turn Thirty.”

Journalism of the period pushed an apocalyptic message about women’s lives. A typical example appeared in Time in 2002, under the headline “Making Time for a Baby,” with a cover photo showing an adorable infant lying on top of an overflowing office inbox. In the article, fertility doctors bemoaned the naïveté of women who sought success within a workplace designed around men—men who had the advantage not only of more durable fertility, but also, traditionally, of a wife to pick up the child-care duties so their professional lives could continue unimpeded.

“Those women who are at the top of their game could have had it all, children and career, if they wanted it,” said one of the physicians quoted. “The problem was, nobody told them the truth about their bodies.” According to the article, a woman’s chances of conceiving declined rapidly after 30—and after 35, she had better prepare for a childless future.

But, according to Sylvia Ann Hewlett, author of Creating a Life: Professional Women and the Quest for Children, the issue was one of wishful thinking rather than straightforward ignorance. Childlessness had become a “creeping non-choice” for middle-class women approaching midlife, she said, and yet, younger women were refusing to heed the warnings: “The fact that the biological clock is real is unwelcome news to my 24-year-old daughter … and she’s pretty typical,” Hewlett wrote.

Like the women who saw themselves in her, Rachel Greene was dealing with new dilemmas thrown up by the modern schedule for living. Deferring settling down brought choices and freedoms, but you still couldn’t barter away the limits of the female body.

In any case, Aniston could hardly be accused of neglecting her personal life. In 1998, she had started dating Brad Pitt—a man so absurdly attractive that he could plausibly take the role of the demi-god Achilles in the 2004 movie Troy. She was “America’s Sweetheart”; he was “the sexiest man in the world.” In 2000, when she was 31, they got married, putting her well ahead on the Rachel Greene plan.

In a time when the intensity of celebrity coverage left few illusions about relationships, Brad and Jen offered a rare instance of purity. “They seemed the most fortunate couple imaginable—two beautiful superstars who had hit the jackpot, earning not only fame and riches but also an enduring love,” wrote Leslie Bennetts in a 2005 Vanity Fair profile.

People weren’t just fans of Brad and Jen individually. They were fans of the marriage, which seemed to represent everything that could be hoped for in a 21st-century sexual union. The couple was even able to joke about their public selves. In a 2001 episode of Friends, Pitt guest stars as Will Colbert, a formerly fat kid from Rachel’s high school who reappears in her life, newly hot and enduringly bitter over her past treatment of him. It was funny to hear Brad Pitt snarl, “I hate Rachel Greene,” because everyone knew that he loved Jennifer Aniston.

Brad Pitt and Aniston at the Emmys in 2004.

When Friends ended in 2004, the obvious next step in the plan—a plan that both had discussed in interviews—would be for them to start a family. Instead, the still childless couple fell apart. Inevitably, a public that had invested passionately in their relationship pored obsessively over the details of their breakup. What could have gone wrong with this golden union? (The end of Friends was also the end of sitcoms’ dominance on network TV: NBC’s next hit in the Must See TV slot was a reality show called The Apprentice, starring Donald Trump.)

Tabloids vied to supply the answer. Was Brad cheating on Jen with Angelina Jolie, his dangerously sexy co-star in the movie Mr. & Mrs. Smith? Had Jen pushed Brad away by refusing to compromise her career for the sake of a baby? Interest reached such feverish heights that when gossip blogger Perez Hilton published the first photos of “Brangelina” together—they were leaked to him by a magazine employee whose publication had been outbid for the pictures by a rival—he picked up enough traffic to crash his site. It was a defining moment in Hilton’s career and in the shift of power from print to online outlets.

When Friends brought its soap opera to its conclusion, it gave the audience everything they wanted. After multiple comings-together and fallings-apart (including getting drunkenly married, getting divorced, having a baby together, and deciding they could never work as a romantic couple), Ross and Rachel end up together. In fact, in the final episode, she chooses Ross over her dream job in Paris, in a last-gasp realization just before her plane takes off. Rachel Greene, the girl who ran away from her wedding to find out who she was supposed to be, has finally found the man worth sacrificing her hard-won career for. Rom-com logic ultimately won.

David Schwimmer and Aniston in Season Eight of Friends: “The One Where Rachel Is Late.”

But with Rachel’s fictional drama tied up, the public still wanted to see Aniston in soap opera, still wanted to see her go through all the varieties of heartbreak and joy, still needed her to stand in for the aughts Everywoman and carry all the anxieties over professionalism, fertility, and femininity that had attached to her. Aniston was about to be cast, against her will this time, in the second great role of her career: as Sad Jen, the tragic third point in a love triangle with Brad Pitt and Angelina Jolie.

For the rest of the decade, there was nothing she could say, and no example of her personal accomplishment or happiness she could show, that would convince the world it was mistaken.

Act II

In January 2005, Pitt and Aniston issued a joint statement announcing their breakup. The collapse of their marriage became a global conversation about the nature of relations between men and women. Even more intrusively, it became a discussion about the condition of Aniston’s uterus and whether she was either willing or able to have the baby her husband apparently wanted.

“Perhaps the strongest clue to the cause of the end of this particular fairytale lies in Pitt’s behaviour on an American television chat show last year,” explained a Guardian story on the couple’s separation. “Eyes welling up, the actor told the nation what he longed for. ‘I’m going to say it: kids, family, I am thinking family,’ he blurted out. But the only sign of issue from his marriage was a joint film project announced last year.”

In her tearful but defiant 2005 cover interview for Vanity Fair, Aniston pointed out the unfairness of this commentary. “A man divorcing would never be accused of choosing career over children,” she said. “That really pissed me off. I’ve never in my life said I didn’t want to have children. I did and I do and I will! The women that inspire me are the ones who have careers and children; why would I want to limit myself? I’ve always wanted to have children, and I would never give up that experience for a career. I want to have it all.”

Jennifer Aniston was about to be cast, against her will this time, in the second great role of her career: as Sad Jen, the tragic third point in a love triangle with Brad Pitt and Angelina Jolie.

After her divorce, Aniston briefly went out with the actor Vince Vaughn and, subsequently, had a year-long relationship with the singer John Mayer (which he later said ended because he was an “asshole”). In 2010, she began dating fellow actor Justin Theroux, and the two were married from August 2015 to February 2018. There was little evidence of her being in a state of permanent pining for her ex-husband. Her romantic life was not, in itself, particularly interesting: TMZ, which preferred its celebrities to come with D.U.I.’s and rehab stints, called Aniston the most boring star in Hollywood.

But TMZ tended to hold itself to a high standard of veracity, only reporting what it could confirm. Other gossip outlets took a more creative approach, and for them, the Aniston-Pitt-Jolie love triangle was too compelling to be allowed to die.

Regardless of what was actually happening in her life, Aniston had been conscripted into being the face of the late-30s female condition, and the assumption was that, without a man and a baby, that condition could only be an unhappy one. Ultimately, the purpose of the “Sad Jen” journalism was not to reflect the truth of Aniston’s life. It was to reflect the worries that adhered to women of childbearing age in general. Alarmists had feared that women were naïve about their bodies. “Sad Jen” was perhaps the era’s greatest work of propaganda for the body clock.

Regardless of what was actually happening in her life, Aniston had been conscripted into being the face of the late-30s female condition, and the assumption was that, without a man and a baby, that condition could only be an unhappy one.

Under the extensive fabrications, though, there was a fragment of truth: in her interviews during this period, Aniston repeatedly stated her intention of becoming a mother, although the scrutiny around this part of her life was clearly uncomfortable for her. When Jonathan Van Meter interviewed her for Vogue, he reported that Aniston was “visibly irritated” by the baby question. “I’ve said it so many times,” she told him. “I’m going to have children. I just know it.”

What she didn’t say publicly was that, during this period, her private life was being consumed by the trying: “It was really hard. I was going through IVF, drinking Chinese teas, you name it. I was throwing everything at it. I would’ve given anything if someone had said to me, ‘Freeze your eggs. Do yourself a favor.’ You just don’t think it,” she told Allure in 2022.

It didn’t help that her post-divorce movies repeatedly returned to the themes of motherhood and marriage. Most awkwardly, there was The Break-Up (2006), in which she and Vaughn played a disintegrating couple. The sentimental drama Marley & Me (2008) cast her opposite Owen Wilson, as a wife balancing her career ambitions with her carefully planned drive for domesticity: in one of the standout scenes, she delivers a heartbreaking portrayal of a miscarriage.

Vince Vaughn and Aniston in the 2006 movie The Break-Up.

In He’s Just Not That into You (2009) she’s the moany girlfriend trying to get an infantile boyfriend (Ben Affleck) to commit. And in The Switch (2010), which she executive-produced, her character is so eager to have a baby that she decides to become a single mother via donor sperm.

In 2009, in an acceptance speech at the Women in Film awards, Aniston joked about the way her movie roles seemed to be dogging her personal life. “It’s funny,” she said, “I kind of noticed something a couple years ago that there seemed to be this strange parallel to the movies I was doing and my life off-screen. It started with, well, The Good Girl. Then that evolved into Rumor Has It, followed by Derailed, and then there was The Break-Up … ” Then came the punch line: “So if any of you have a project titled Everlasting Love with an Adult, Stable Male …

But when she said this, she was single and 40. Aniston would never have the baby the tabloids had so often promised. In 2021, The Hollywood Reporter asked her how her post-Friends life had differed from her expectations. “The career was one thing,” Aniston replied. “I didn’t know what was coming, and that’s been nothing but blessed. It’s a different caliber of work but I love it, no matter what, even if it’s a terribly reviewed, dumb comedy, it doesn’t matter if it brings me joy.”

She continued: “It was more personal stuff that I had expectations about that sort of shape-shifted, so to speak. That was what was jarring, that we all had an idea of what the future was going to be and we were going to go hunker down and focus on this or that and then it all just changed overnight, and that was it.”

Perhaps some would classify Aniston among those women for whom childlessness was a “creeping non-choice,” as Sylvia Ann Hewlett described it. It’s worth noting, though, that a woman with Aniston’s resources has more options than most. Even without a partner, she could, like Jolie, have pursued adoption; or she could have had a baby via surrogacy.

She chose not to, which pokes some holes in the tabloid portrayal of her as a woman obsessed by baby hunger. And, despite all the ways Aniston has been recruited to stand for the anguished tussle between career and motherhood, her ultimate contentment may be the most significant fact of all. Infertility is a source of deep grief—and yet, counter to the persistent message of the “Sad Jen” confection, husbands and children do not bring automatic contentment for women.

Beyond the aughts’ concerted efforts to terrify women into reproduction lay an even greater fear: What if women didn’t need a man and a baby to be happy? (Or, at any rate, what if they would be equally unhappy either way?) The insistence that women would inevitably find misery if they didn’t follow the plan had been presented as well-intentioned advice, but perhaps it was closer to emotional blackmail: if women could be harrowed into shacking up and reproducing regardless of the immediate costs they bore, the workplace could be spared the bother of reforming itself to better fit female employees, who make up 47 percent of the total U.S. workforce.

The Hollywood Reporter interview was, in part, given to promote The Morning Show, the Apple TV+ drama that marked Aniston’s first lead role in a television series since Friends. The evolution of television that started with the cable wars of the late 1990s had continued through the following decades and escalated again with the arrival of streaming services. This had led to a resurgence of interest in Friends, and not only among older viewers who wanted a nostalgic re-watch. Millennials who would have been children at the time of the first broadcast, and Gen Z–ers, who wouldn’t even have been born, were every bit as avid.

“The career was one thing.... That’s been nothing but blessed.... It was more personal stuff that I had expectations about that sort of shape-shifted, so to speak.”

Friends had been a triumph for Aniston, but it had also trapped her in various less interesting iterations of the Rachel Greene character. Now television had matured to the point where it could again offer her a role to match her talents. After over a decade of being largely disregarded for her cinematic work, Aniston won a Screen Actors Guild Award for her performance on The Morning Show. In it, she plays Alex Levy, a TV news anchor whose male co-host, Mitch Kessler (played by Steve Carell), is fired for sexual misconduct.

It’s a storyline that clearly maps the real-life falls of men like Matt Lauer, Charlie Rose, and Bill O’Reilly, all of whom lost their jobs after allegations against them emerged in the aftermath of the Harvey Weinstein case. (Lauer, Rose, and O’Reilly all deny the accusations.)

The scandals exposed by the #MeToo movement showed that many men had little appetite for re-invention. Instead, they clung to dominance, using sex to assert their control over the women who had encroached on the workplace.

Aniston and Steve Carell in The Morning Show.

And then, in 2016, disenfranchised masculinity found political expression in the election of Aniston’s Must-See TV successor, Donald Trump. #MeToo, which emerged as a mass movement in 2017, was essentially the backlash to the backlash: out of the betrayed promise of a female future came a moment of consciousness-raising in which many women not only acknowledged for the first time the harms done to them by men in positions of power, but also realized for the first time, through other women’s testimony, how near universal such encounters with predators were.

But while MeToo offered a form of wild justice, women’s formal rights in the United States were slipping away. In 2012, The End of Men author Hanna Rosin had regarded the professional, sexual, and reproductive freedoms won by women in the previous decades as non-negotiable. “A society that has become utterly dependent on the unfettered ambition of women cannot possibly, with a straight face, reopen the debate about contraception,” she wrote confidently—and, it transpired, wrongly.

Trump’s appointment of conservative justices to the Supreme Court enabled the overturning of Roe v. Wade in 2022, ending American women’s constitutional right to abortion. Speaking after the decision, Justice Clarence Thomas suggested that the same legal argument could also be deployed against (among other decisions) Griswold v. Connecticut, which had established the right to contraception. The window of deferred maternity enjoyed by women had allowed both female liberty and male anxiety to flourish. Now, in the United States at least, there are determined efforts to close it.

This does not mean women will necessarily comply: one of the lessons of the demographic data is that, even with efforts to compel women toward childbearing, educated women will still have fewer babies and will do so later in their lives, if at all. But exercising this preference becomes dramatically more difficult without accessible legal abortion.

In 2004, Rachel Greene and Jennifer Aniston had stood as twin visions of female liberty: the fictional one got to “have it all,” while the real one underwent a more complicated mixture of disappointments and accomplishments but, ultimately, built a life that must, by any standards, be considered a happy and successful one.

Almost uniquely among women who experienced the most extreme form of aughts fame, Aniston did not become a prisoner of her image, however relentless the efforts to impose that image on her. Her celebrity persona existed in parallel to a real life in which she found her own fulfillment. For the young women of the present-day United States, that freedom to make their own plan, with all the attendant risks and rewards, can no longer be taken for granted.

Sarah Ditum is a London-based journalist. Her book, Toxic, will be published on January 23