It was a perfect spring Los Angeles day in 2005 when Paris and Nicky Hilton walked, hand in hand, into a throng of waiting paparazzi. The cameras clicked and popped as the socialites turned to one another with knowing giggles, safe in the knowledge they’d soon be in every gossip column thanks to their T-shirts. Nicky’s bore the words “Team Aniston” while her sister Paris’s read, “Team Jolie”.
The shirts had been acquired at cult Beverly Hills boutique Kitson, whose owner Fraser Ross had hastily monopolised on a growing celebrity story: the split of Brad Pitt and Friends actor Jennifer Aniston, and his rumoured new romance with his sultry Mr & Mrs Smith co-star Angelina Jolie.
Those Kitson T-shirts were just the start of a tabloid narrative that pitted Jolie and Aniston against one another for well over a decade. Even when Jolie and Pitt announced their own divorce in 2016, attention turned to Aniston, with reports pondering her reaction (which she, of course, never gave).
Their A-list love triangle has proven irresistible to tabloids and magazines. Aniston and Jolie were painted as bitter rivals, despite neither of them ever commenting on the other. In fact, Aniston had said in 2005 that she never overtly blamed Jolie for her divorce, only remarking, “It’s just complicated” (you can say that again).
And while not immune to that media cacophony, somehow Brad Pitt’s nice guy image remained largely intact. Aniston herself helped Pitt close the chapter on any post-split bad blood when she was photographed with her hand on his chest at the 2020 Screen Actors Guild (SAG) awards, where he won an award for his turn in Once Upon A Time In Hollywood. Later that year, they both appeared on Zoom for a pandemic charity event, during which she called him “honey”.
Yet his protracted divorce battle from Angelina Jolie, which was only just finalised on 30 December, eight years after they announced their split, told a different story. Since 2022, Jolie has filed a series of legal documents detailing claims of emotional and physical abuse. Her lawyers alleged Pitt grabbed and pushed Jolie during a physical altercation, during which it was claimed Pitt also assaulted two of their children. Pitt denied those allegations and, in 2021, was awarded joint custody of the children after a long and acrimonious court battle over their living arrangements. In June, their daughter Shiloh submitted a petition to a Los Angeles court to drop Pitt from her surname, and two more of the couple’s children have reportedly stopped using their father’s name too, in solidarity with Jolie.
These, at times, shocking court allegations have somehow barely registered on the usually sensitive public cancel-ometer for Pitt. Indeed, he has maintained a cheerful presence on the publicity circuit – especially during awards season. A recent interview for GQ magazine, alongside best pal George Clooney, to promote their latest film Wolfs, was a celebration of their best buddy status and Hollywood clout.
As Pitt promoted Wolfs, Jolie attended the premiere of her critically acclaimed Maria Callas biopic, Maria. At the time, it was confirmed by an organiser that the event had been planned with meticulous care to ensure that Jolie and Pitt would never come face to face.
It was there that Pitt made his red-carpet debut with non-celeb, thirtysomething girlfriend Ines de Ramon. Allegedly, they are keen to get married, and Pitt wants a “fresh start”.
Jolie, who turns 50 in June, is getting back into her Hollywood career after stepping away to “heal”. Sources close to Jolie, who has eschewed A-list cliques for most of her life, say that she has been embracing a newfound solidarity with fellow awards-circuit actors such as Demi Moore, Salma Hayek and Kate Winslet, whom she was seen hugging at the recent Critics Choice ceremony in LA. She was said to have been “devastated” at her snub in the Oscar nominations last month, with reports suggesting that Hollywood has sided with Pitt, and that the voting could be a reflection of industry pals not wishing to “upset” Pitt by putting Jolie in the run for Best Actress for which she had been so hotly tipped.
So how has Brad, now 61, kept his Hollywood boy next door status intact? Tabloid snark is, of course, always quicker to pinpoint any women at fault; Angelina Jolie and Jennifer Aniston learned this the hard way. It was just five years after their intimate (by Hollywood standards, anyway) $1m, 200-person wedding on a Malibu clifftop, during which Aniston promised to always make Pitt’s “favourite banana milkshake”, that the most golden of A-list couples announced they were over. Their rather pointed statement added, “We would like to explain that our separation is not the result of any of the speculation reported by the tabloid media.”
The “speculation” was, of course, the flurry of rumours about Pitt and Jolie, who were said to have fallen for one another while shooting Mr & Mrs Smith, in which they played a bored married couple who discovered they were both assassins. Just a month after Aniston filed for divorce, US Weekly had the first exclusive paparazzi pictures of the new couple, sold for hundreds of thousands of dollars, as they walked on a beach in Kenya with Jolie’s adopted son Maddox.
Then, in July of that year, a sexy shoot for W magazine to promote Mr & Mrs Smith dropped. Entitled “Domestic Bliss”, the shoot provocatively depicted Brangelina as a devoted married couple, with children, at a time when they had been skirting romance rumours. During an interview with Vanity Fair in August, Aniston said of that shoot, “There’s a sensitivity chip that’s missing.” She added, “I just don’t know what happened ... I feel as if I’m trying to scrounge around and pick up the pieces in the midst of this media circus.”
Arguably, that media circus cast a long shadow across the women’s professional lives, while leaving Brad’s untouched. In the years that followed, despite working a lot, neither appeared in a film that compared to their previously critically acclaimed films like The Good Girl (Aniston) and Girl, Interrupted (Jolie). Brad Pitt’s career, however, went from strength to strength, with turns in the lauded Moneyball, Burn After Reading, The Curious Case of Benjamin Button and Inglourious Basterds all coming in the immediate aftermath of the romantic controversy. He also retained control of Plan B, the extremely successful production company he and Aniston founded with partner Brad Grey, which has gone on to make Oscar-winning films like Moonlight and 12 Years A Slave, strengthening Pitt’s Hollywood clout.
Joli, meanwhile, was regularly painted as the villain in all this, the cold, and achingly cool other woman. Brad Pitt was still seen as Hollywood’s approachable leading man, with his sunny midwestern charm. “There was a sort of belief that Jolie, mostly known for wearing vials of blood and kissing her brother [James Haven] on a red carpet, had cast some kind of spell on Brad for him to leave Jen like that,” says one Hollywood insider.
Brangelina may have finalised their divorce in December last year, but their feud over their French vineyard Château Miraval is ongoing. It has been a stage for an onslaught of intimate details of their relationship’s demise to play out, dubbed the “War of the Rosé”.
A short explanation of the extensive legal wrangle: the couple bought the French winery together in 2011 and were even married there. Years after their split, however, Jolie sold her shares to a subsidiary of the Stoli Group – the parent company of the famed vodka brand – which Pitt saw as an action that “sought to inflict harm” because the sale blocked Pitt from obtaining majority-shareholder status. Jolie, according to legal filings, says that Pitt was trying to “silence her” with an NDA before he would agree to sell up.
In one set of papers, Jolie claims that Pitt’s final words in their marriage were, “F**k you. F**k you all”. Jolie added that he had called her a “b***h” and shook her by the shoulders. All allegations were denied by Pitt, who has accused Jolie of seeking to deliberately undermine his businesses.
Their children Maddox, Pax, Zahara, Shiloh, and twins Vivienne and Knox, have taken their mother’s side, much to Pitt’s anguish. In 2022, news surfaced that Brad and Angelina’s adopted son Pax had shared a scathing account of how he felt about his father on his private Instagram story on Father’s Day in 2020. In the leaked screenshot, Pax wrote over a photograph of Brad accepting an Oscar for his performance in Once Upon A Time In Hollywood. “Happy Father's Day to this world-class a**hole!” the post read. The teenager allegedly claimed the Hollywood star made his four youngest children “tremble in fear” and “made the lives of those closest to [Pax] a constant hell”.
Reports suggested that Pitt has been “heartbroken” about the fallout with his children. Now, in the wake of their long-awaited divorce, Pitt and Jolie must find their “new normal”, something that was demonstrated by their “near-miss” appearances at the Venice Film Festival. While Jolie recalibrates her career, Pitt claimed in 2022 that his own could be “on its last legs”, but he currently has 10 upcoming projects listed on IMDB and is widely expected to make an appearance on the red carpet for the Oscars.
A recent report by New York magazine explained that Pitt’s lovability is down to the idea that audiences feel they “know” him. It is certainly inevitable that there are many more chapters to come for the man who has dominated pop culture for a generation.
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