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In the biggest tabloid love triangle of the 2000s, there was never a right kind of woman to be.
In the Purity Chronicles, Vox looks back at the sexual and gendered mores of the late ’90s and 2000s, one pop culture phenomenon at a time. Read more here.
There was a moment in the 2000s when you could tell the world exactly what kind of woman you were trying to be by who you were rooting for in the Brad Pitt-Angelina Jolie-Jennifer Aniston love triangle.
Being Team Aniston meant you believed in the sanctity of marriage; that you aspired to an achievable, girl-next-door glamor; that you wanted to be cool in a “hottest prom queen of the decade” kind of way.
Being Team Jolie meant you believed that love was stronger than marriage; that you aspired to an otherworldly glamor; that you wanted to be cool in a “cosmopolitan global citizen with lots of tattoos” kind of a way.
It felt as though one of those women was the right kind of woman, and if we could all just decide who she was, then we would know what kind of woman we should be, too. But which one was it?
Nobody rooted for Brad Pitt in that love triangle, exactly, because that wasn’t what he was there for. Brad Pitt didn’t have to prove that he was the right kind of man; that was already assumed. He existed to choose the right woman, and to prove her rightness with his approval.
But if the past few years of headlines prove anything, it’s that in the long term, none of the women in this story ever really got to be right.
Pitt and Jolie divorced in 2016, and now their messy custody battle has been dragged into the courts, with Jolie alleging that Pitt behaved violently toward her and their children and Pitt’s supporters accusing Jolie of a smear campaign. Meanwhile, Aniston revealed in a December interview with Allure that she struggled with infertility throughout her marriage to Pitt. The stories are sad and disturbing, but they’re also oddly familiar.
When Pitt ended his marriage with Aniston in 2005 to enter a relationship with Jolie, he launched what would become one of the most potent and profitable tabloid narratives of the era. The storyline was set subliminally before anyone even confirmed the basic events, when Pitt masterminded a photoshoot with Jolie in W magazine that showed the two of them together presiding over a house full of children, while the press darkly implied that Aniston had chosen a nascent film career over kids. That story was: One of these women deserves to have Brad Pitt’s babies. (“I’ll have your baby, Brad,” said Eva Longoria’s T-shirt, while “Team Aniston” and “Team Jolie” shirts flew off the shelves.) In a way, that’s still the story we’re telling now: One of these women deserves to mother Brad Pitt’s children. Which one are you rooting for?
Questions about fatherhood, meanwhile, become significant by their absence. The issue of which woman Brad Pitt deserves to have kids with is rarely asked. Instead, we assume that he deserves whomever he happens to want.
The big question of this story is who is the winner, but you don’t need to struggle to win if you’ve already won. The only person involved to whom that applied was Brad Pitt. He needed no trophy of his own because his trophy was his whole life.
Aniston and Jolie never actually got to win. They were always on the brink of having won, always on the brink of having proven themselves worthy of love, always contingent. They were never allowed to have won.
As Pitt, Jolie, and Aniston return to their old tropes, each of them is trying to rewrite the narrative in their own favor, just like they did last time. To see how they’re doing it now, we’ll have to look at how they did it the first time around, and what they stand to gain now.
“Is Brad to be blamed here?”
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Jennifer Aniston and Brad Pitt during the 54th Annual Primetime Emmy Awards, Los Angeles, 2002.
In 2004, the world seemed confident that Jennifer Aniston was a woman made for motherhood. She was just coming off Friends, where she spent the last few seasons playing a single mother who is also successful in both her career and in love. Sunkissed and golden and effortlessly likable, Aniston seemed poised to follow in her character’s footsteps. Only in real life, she would have Hollywood’s greatest male sex symbol at her side all the while.
In 1999, a year before Aniston and Pitt were married, the Globe announced that Aniston was “about to become a bride and a mother.” “Jennifer Aniston: Brad, Babies & a Breakout Movie” read the cover of People magazine when Aniston appeared — not pregnant — in 2002. She and Pitt would, W magazine reported in 2003, be having somewhere between two and seven children together. When Aniston hosted SNL in 2004, she appeared in a sketch hounded by paparazzi who shrieked in chorus, “When are you gonna have a baby?!”
Aniston was, as Guardian columnist Zoe Williams argued in 2022, an ideal woman for the post-feminist ’90s, which is to say she was most exceptional in how deeply, sweetly approachable she appeared to be. Williams argues you can see Aniston’s perfection for the era in her famous hair: “not too long (attention-seeking), nor too short (feminist/independent), not too blond (conventional) or too dark (vampy), not too shiny (airhead) nor in any way dull (frigid), [it] was the perfect, man-pleasing hair for the late 20th-century woman.”
Aniston was considered a little bit lowbrow, too, which made it all the more obvious that she was meant to be a mother. Aniston was America’s sweetheart, sure, but she was a TV actress in the era before people started talking about TV shows like they were serious art. If she wanted to put her career on hold to have a baby while Pitt was off making movies and trying to land an Oscar, who would it hurt?
Angelina Jolie was another story altogether. For years, she had been in many ways the Mary Magdalene to Aniston’s Virgin Mary, a wild child who seemed to be all sex appeal and taboo-breaking. Sure, she won an Oscar for Girl Interrupted, but then she followed it up by smooching her brother. In 2006, Vanity Fair would succinctly sum up Jolie’s image in this era as “a tattooed vixen with a taste for bisexuality, heroin, brotherly incest, mental institutions, and wearing her husbands’ blood.” Also her hair was long (attention-seeking) and dark (vampy).
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Angelina Jolie poses with her Oscar at the Academy Awards in 2000.
Jolie, unlike Aniston, did not seem born to be a maternal figure. If Aniston’s most iconic role of the 2000s saw her navigating single motherhood with a devoted team of friends at her side, Jolie’s saw her shooting up a mall to fully express her disgust with the idea of becoming a housewife in the suburbs.
Moreover, Jolie was a figure of worrying ambition. She had an Oscar. She didn’t seem likely to put her own career aside to raise children while her husband went off to try to win his own Oscar.
But in 2002, Jolie adopted her first child, Maddox, an orphan from Cambodia. As Anne Helen Petersen documented in BuzzFeed, she began to tweak her image, at first a little, and then a lot. She got herself photographed playing with her kid in the park, and she started to talk to the press a lot about her humanitarian concerns. She became a UN goodwill ambassador. At the time that she became involved with Pitt, Jolie was, as Vanity Fair put it, morphing into “a globe-trotting humanitarian who seemed to be channeling Audrey Hepburn.”
At the beginning of 2004, Aniston and Pitt began to tell the press they were planning to have a baby soon. Friends was winding down in January of 2005, and Pitt would wrap Mr. and Mrs. Smith in February of the same year. Their schedules were lining up. Everything was falling into place.
Instead, in January of 2005, Aniston and Pitt announced their divorce. In April of that year, Us Weekly published photographs of Pitt with Jolie and Maddox on a beach in Kenya, looking every inch the family unit. Pitt, clearly, had swapped one would-be mother for another.
Wild, sexy, unpredictable Jolie was tailor-made for a villain narrative, for the idea that she stole the hottest man in Hollywood from the beloved star of Friends. But her years of image reshaping meant that she also had a counternarrative ready and waiting for her to step into. She was a serious person with serious concerns, and it wasn’t her fault if she also happened to be so gorgeous there was no way Brad Pitt could resist her. For the first time, the possibility emerged that perhaps Aniston was not, after all, the right sort of woman.
As the divorce progressed, onlookers took sides (see: the above T-shirts). A 2008 item for Yahoo was able to work both sides of the story at once: Aniston “comes across looking a tad bit pathetic at times,” but Jolie was “a mastermind manipulator … willing to do whatever it takes to get her way.”
By the close of the decade, with three adopted children and three biological, Brangelina were no longer adulterers but saints. They were A-listers who gave the power of their wealth and attention to worthy causes, an Oscar winner and an Oscar hopeful and their gaggle of beautiful children. In the end, motherhood was to be the ruin of the Betty and the redemption of the Veronica.
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Brad Pitt, Angelina Jolie, and kids arrive at the Venice Film Festival in 2007.
Aniston, childless and unmarried and with her biggest hit fading into the past, was painted as the loser, the spinster: poor pathetic Jen. Dark rumors swirled that maybe she hadn’t even wanted children, that maybe she’d picked her career over kids, but her fanbase didn’t believe it. Part of loving her became wishing she would finally find happiness, which meant true love and children. The perennial questions tabloids began to ask of Aniston was: When was it going to happen for her?
The question of Pitt and his culpability or lack thereof in the whole story was, noticeably, missing. In the narrative of the tabloids, Aniston and Jolie are the agents acting upon Pitt, while he and his golden beauty, his charm, his credibility all rest inviolate and whole. He was the trophy for whomever proved herself worthy of him.
“Is Brad to be blamed here?” demanded gossip site Koimoi as late as 2020, after alleging that Jolie “was a temptress on the set” of Mr. and Mrs. Smith. “Angelina is one of the most beautiful women in the world, it might be hard to resist.”
The moral of this story is: you can be a good woman, but if you’re not a mother, your goodness is sad. You can be an unruly woman, but if you are seen mothering in public, your unruliness has been tamed and we no longer have to worry about you.
To be a mother is to be a woman fulfilling her duty. Then we may consider you tamed, passive. We tell you that you win, but in fact you have been won.
“Brad has owned everything he’s responsible for from day one”
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Brad Pitt with Quentin Tarantino and Margot Robbie at the 2023 Golden Globes.
Pitt and Jolie divorced in 2016, uncoupling the elements of Brangelina to be a portmanteau no more. At the time, there were vague stories about an altercation on the family’s private plane, but the story was difficult to follow and seemed to make little impact on Pitt’s reputation. What we knew then was this: Pitt, apparently, had been drunk, and he’d had some sort of confrontation with Jolie and with 15-year-old Maddox, which Jolie said had gotten “physical” and Pitt insisted had not. The FBI investigated and filed no charges.
In September of 2016, Jolie filed for divorce and demanded sole custody of their six children. Pitt countersued for full custody for himself. By the end of the year, they’d reached a provisional agreement in which Jolie would have full custody temporarily. Meanwhile, battle for control of the narrative played out in the press.
Jolie initially took her story to TMZ, which loves a scandal and knows no loyalties. But the print tabloids, who know where their bread is buttered, were immediately Team Pitt. “Her Plot To Destroy Brad,” screamed Us Weekly, in an article that claimed Jolie was running a vicious and untrue smear campaign. Meanwhile, People had “Brad’s Side of the Story.”
In May of 2017, Pitt sat for a soulful cover story in GQ and talked about “looking at my weaknesses and failures and owning my side of the street.” He had, Vanity Fair concluded, “won hearts and minds.”
Jolie, meanwhile, was keeping her side of the story close to the chest. She declined to comment on the circumstances of the divorce, but profiles about her increasingly dwelled on her rich-lady kookiness, the sense that her many foreign adoptions were the result not of an admirable global consciousness but rather of a white savior complex. Pitt won the day.
The story probably would have stayed vague and amorphous and easy for Pitt to talk his way through had he not chosen to drag it into the courts.
In February of 2022, Pitt sued Jolie over the vineyard they used to mutually own. They bought it together in 2008 and married there in 2014. Pitt claims that when they divorced in 2016, they agreed neither one of them would sell their shares without the other’s permission. However, in 2021, Jolie sold her shares to Tenute del Mondo, the wine division of Russian liquor company Stoli. Pitt’s suit says the sale undermines his own investment in the business.
Jolie, meanwhile, says the no-sale agreement never existed. According to Jolie, she tried to get Pitt to buy out her shares in 2021. When sales negotiations failed, she went over his head, talked to a judge, and got legal approval to sell her shares. Tenute del Mondo took over Jolie’s shares and promptly sued Pitt for mismanaging the vineyard, and then Pitt countersued them and sued Jolie for good measure too.
As for why those sales negotiations between Pitt and Jolie failed: The New York Times reported in October of last year that the sale fell apart because Pitt wanted Jolie to sign a nondisclosure agreement pledging never to publicly discuss what happened on that plane ride in 2016. When she wouldn’t do it, he refused to buy her out.
Now Jolie is publicly discussing the plane ride in detail for the first time as part of her countersuit against Pitt. She has also anonymously filed a Freedom of Information Act request with the FBI (first discovered by Politico in April) seeking more information on the FBI’s report on the plane ride from 2016 and its decision not to press charges against Pitt.
The redacted FBI report first leaked to the public in August 2022, and its contents are disturbing. The report describes a drunk Pitt describing one of his children (likely Maddox) as a “fucking Columbine kid,” grabbing and shaking Jolie, punching the ceiling next to her head, and pouring beer over her as she slept. The report says he menaced one of the children (again, likely Maddox) and injured Jolie when she prevented Pitt from attacking the child. It also states that the investigative agent has provided the US attorney’s office with “copies of a probable cause statement related to this incident.”
As the report’s story filtered out, Pitt went on the offensive against Jolie in the print tabloids. The story had already been investigated, he argued, and Jolie was only making it public now in order to hurt him. “What are the motivations of a person to take up court time and public resources in filing an anonymous FOIA request for material they have had for years?” demanded a “source close to Pitt” in People magazine. “There’s only one: to inflict the most amount of pain on her ex.” (Jolie’s attorneys maintained she was only trying to find out why no charges were ever filed against Pitt.)
In October, Jolie filed her countersuit, which made her accusations against Pitt more explicit than they were in the redacted FBI report. The countersuit alleges that Pitt choked one of the children and struck another across the face, and that in addition to pouring beer on Jolie, he poured red wine on the children.
“Angelina Jolie is on a smear campaign against Brad Pitt, hashing and rehashing the same allegations she’s made for years — allegations that have fallen flat with authorities — this according to sources close to Brad,” reported TMZ.
Pitt is the legal aggressor here: He sued Jolie. But his allies in the press continually argue that the reason their custody battle has made it to the courts is that Jolie is caught up in some sort of vengeful campaign to destroy Pitt’s life. In the popular narrative of this lawsuit, Pitt’s own culpability is erased, even as he loudly congratulates himself on his ability to own his mistakes.
“Brad has owned everything he’s responsible for from day one — unlike the other side,” Pitt’s lawyer told Page Six. “He’s not going to own anything he didn’t do. He has been on the receiving end of every type of personal attack and misrepresentation.”
This move is in many ways a return to the narrative of 2005. “It’s hard not to notice how the current moment is replaying early images we associate with Brangelina — Jolie as the bad influence, Pitt as the innocent charmer caught in the drama,” mused Angelica Jade Bastién in New York magazine. Back then, Jolie was able to turn her image around, to win the PR battle against a marginalized Aniston. This war, though, is different.
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Angelina Jolie during an event celebrating the reauthorization of the Violence Against Women Act (VAWA) in the East Room of the White House on March 16, 2022.
In the early 2000s, Pitt and Jolie were at close to equal levels of fame, celebrity peers. Now, Pitt has far more power than Jolie. His acting career has flourished and he finally got that Oscar, while Jolie no longer seems interested in her own acting and hasn’t made a notable hit since Maleficent in 2014. Pitt’s second career as a producer has paid off with multiple credible hits (Twelve Years a Slave, Moonlight, Promising Young Women, She Said) while Jolie’s second career as a director has stalled after a series of flops and credibility-sapping misfires.
When Jolie turned her image around in the 2000s, she did so through the performance of motherhood: picture after picture of Jolie as a loving parent with her brood of children. For Pitt, such a performance doesn’t seem to be necessary. No one has photographed him with his children or indeed has any proof he has been in their lives since that plane ride in 2016, but that doesn’t seem to matter for this fight: Pitt can still earn glowing headlines from the tabloids just by remarking that he’s proud of his kids. Fatherhood or the lack thereof does not have the same iconographic power that motherhood does.
And in this era of Me Too backlash, Pitt’s side of the story gets an extra leg up from an internet army eager to burnish his claims. An NBC News study found that social media figures who built up a following bashing Amber Heard to their followers now have Jolie in their crosshairs, and that they’re calling Pitt and Jolie’s legal battle “the next Depp v. Heard.”
At the heart of Pitt’s strategy, though, is an attack on Jolie’s motherhood. Pitt, like Woody Allen before him, is claiming that his ex-wife is turning their children against him in a baseless bid for vengeance. “BRAD PITT SOURCES: ANGELINA HAS POISONED KIDS AGAINST HIM … She’s On A Hate Campaign,” declared TMZ in October. It went on to quote an anonymous source claiming Pitt has a “limited and strained relationship [with his kids], because of her campaign of alienation.” Pitt is saying that Jolie is not a good mother, that her love for their children is unnatural and manipulative. Angelina Jolie, according to Pitt’s current narrative, no longer deserves to have Brad Pitt’s babies.
The moral of this story is: You can be a good mother, but without power, that doesn’t mean people consider your story worth believing. You can be a good mother, but that doesn’t necessarily mean anything if a man questions your goodness.
“I don’t have anything to hide at this point”
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Jennifer Aniston filming on location for The Morning Show at the Mercer Hotel on September 26, 2022, in New York City.
If Jolie’s star has fallen since the 2000s, Aniston’s has risen. Friends nostalgia only keeps growing, and HBO Max’s reunion special last May was a blockbuster hit. With the success of Apple TV’s The Morning Show, on which she both co-stars and works as a producer, Aniston now has another big hit — and since this one isn’t a comedy, she’s been able to expand the public’s perception of her range.
Now twice-divorced and still childless, Aniston is no longer America’s girl next door. She’s been promoted.
“At 50 years old, Jennifer Aniston’s brand is Boss,” declared Lainey Gossip in 2019, as Aniston posed for the cover of InStyle in heaps of gold jewelry, face stern. “She’s been a boss for years with her own projects but it was never actively part of her image then. Now? Boss is the message now. And it looks great on her.”
In interviews, Aniston has begun positioning herself as an ambitious striver who still has more to show the world. “I was the girl next door, the damsel in distress, the brokenhearted — your traditional rom-com themes. And at a certain point, it was like, ‘Can’t we do something else?’” she told the Hollywood Reporter in 2021. “There are still certain directors I’d love to work with, ones who have their pick of who they like, and sometimes I want to go, ‘I’d love to be part of that club.’” Wes Anderson, she thought, would be interesting.
Pitt, who Lainey Gossip calls “cunning as a Kardashian” in his subtle understanding of the publicity game, seems to have picked up on the shifting heat metrics. One of his hottest publicity moments since his divorce from Jolie came in 2020, when he and Aniston ran into each other backstage at the SAG Awards: Pitt there on the Oscar trail for Once Upon a Time in Hollywood, Aniston there for The Morning Show. Both would win trophies that night.
In photos they can be seen beaming at each other with delight and embracing. Then Aniston turns to walk away — and Pitt, gazing wistfully after her, keeps holding onto her wrist. The moment was so celebrated it instantly earned a name: The Hand Clasp.
Emma McIntyre/Getty Images for Turner
The Hand Clasp.
“I’m already writing the fanfic in my mind and I’m not even sorry about it,” said Cosmo.
“I don’t think there is a person in the world that doesn’t want to be grabbed by Brad Pitt that way,” opined Blast.
“Now you must leave us to die in peace,” decreed the Cut.
As Bastien has noted, Pitt seems to frequently remind people of how much they like his exes whenever his image could use a little extra zhuzh; just last summer, he did a friendly sit-down with Gwyneth Paltrow. A moment with Aniston on her upswing makes for a particularly potent reminder of why the fantasy of Brad Pitt is so compelling: Here is a man who is secure enough in himself to date interesting women, and to remain good friends with them after it all ends.
But Aniston’s success can also be a reminder of what is available to women who do not win the motherhood races. She’s divorced (twice), and she’s still happy. She doesn’t have children, and she is still successful. In her 50s, she’s revitalizing and reimagining her career.
So when Aniston told Allure about her infertility struggles this fall, she did so from a place of strength, as the boss who doesn’t need a man and doesn’t need babies.
In the 2000s, she told Allure, there was a narrative “that I was just selfish. I just cared about my career. And God forbid a woman is successful and doesn’t have a child. And the reason my husband left me, why we broke up and ended our marriage, was because I wouldn’t give him a kid. It was absolute lies. I don’t have anything to hide at this point.” She doesn’t have anything to hide because she has the power now.
This entire story is, in the end, a story about power: who has the power to win America’s love. When Aniston was young and hungry and coming off a hit show, she didn’t have the power to keep the tabloids from rendering her pathetic, but she does now. Back then, Jolie had the power to salvage her image from a press intent on painting her as a homewrecker, but now, she’s lost enough standing that she’s falling prey to the same misogynistic rumor-mongering that took down Amber Heard.
In 2004, Brad Pitt had the power to render his own presence in this story invisible, unremarkable, hegemonic. He’s trying to pull off the same trick here. Mostly, it’s working.