It’s been 20 years since Brad Pitt ‘left’ Jennifer Aniston for Angelina Jolie – have we learned anything? – Bundlezy

It’s been 20 years since Brad Pitt ‘left’ Jennifer Aniston for Angelina Jolie – have we learned anything?

Brad Pitt and Angelina Jolie smiling in a scene from movie Mr and Mrs Smith.
It’s been two decades since Brad Pitt and Angelina Jolie fell in love while filming Mr and Mrs. Smith (Picture: 20th Century Fox/ Kobal/ Rex/ Shutterstock)

Ready to feel old? It’s been 20 years since one of the biggest events in tabloid media history: Angelina Jolie and Brad Pitt filming Mr. and Mrs. Smith, which happened concurrently with the end of his marriage to Jennifer Aniston

The film started shooting in early 2004, while Brad was still very much married to Jennifer Aniston. At the time, Brad and Jen were considered Hollywood royalty.

They’d been married since 2000 and were the golden couple: glamorous, low-drama, and wildly famous. Then came Mr. and Mrs. Smith.

Brad was cast opposite Angelina Jolie, who already had a reputation for being edgy, bold, and wildly magnetic. From the minute filming began, rumours flew that something was happening between the two stars.

Brad and Jen announced their separation in January 2005 and finalized their divorce in October. Just a few months later, paparazzi captured now-infamous photos of Brad, Angelina, and her son Maddox playing on a beach in Kenya.

They never officially confirmed a relationship until the following year, but the timeline pretty much wrote itself – and so did the tabloid headlines.

Editorial use only. No book cover usage. Mandatory Credit: Photo by Stephen Vaughan/20th Century Fox/Kobal/REX/Shutterstock (5884806j) Brad Pitt, Angelina Jolie Mr and Mrs Smith - 2005 Director: Doug Liman 20th Century Fox USA Scene Still Mr & Mrs Smith
The sultry film got rumour mills spinning (Picture: Stephen Vaughan/ 20th Century Fox/ Kobal/ Rex/ Shutterstock)
For Editorial Use - Credit Studio Only Mandatory Credit: Photo by THA/REX/Shutterstock (15072593si) Film Still from "Mr. & Mrs. Smith" Brad Pitt, Angelina Jolie ? 2005 20th Century Fox Photo Credit: Stephen Vaughn Studio Publicity Film Stills
Angelina and Brad have always denied that they slept together while he was married to Jenn
(Picture: THA/ Rex/ Shutterstock)
Editorial use only. No book cover usage. Mandatory Credit: Photo by Stephen Vaughan/20th Century Fox/Kobal/REX/Shutterstock (5884806s) Brad Pitt, Angelina Jolie Mr and Mrs Smith - 2005 Director: Doug Liman 20th Century Fox USA Scene Still Mr & Mrs Smith
But it was clear that they discovered their romantic chemistry while filming the spy movie
(Picture: Stephen Vaughan/ 20th Century Fox/ Kobal/ Rex/ Shutterstock)

The media circus that followed wasn’t just gossip, it was a revealing snapshot of how deeply sexist and one-sided pop culture could be (and honestly, still is).

Right out of the gate, the media locked Jennifer Aniston into a role: the abandoned, heartbroken wife.

Tabloids started calling her ‘Poor Jen’ on repeat, painting her as this sad, lonely woman who just couldn’t hold onto her man. It was sympathetic, sure, but it also made her seem passive, like her only storyline was being left behind.

Meanwhile, Angelina Jolie was cast as the villain. She was the ‘homewrecker,’ the ‘temptress,’ the sultry siren who stole Brad away.

The term ‘homewrecker’ itself is soaked in sexist judgment, it’s almost always used to shame women, not the men they supposedly ‘lure’ away.

And then there was Brad. Somehow, the guy at the center of all this? Barely got touched. He was either the poor, bored husband stuck in a lifeless marriage or the helpless man who just couldn’t resist Angelina’s ‘exotic’ allure. If anything, the whole thing only helped his career,

Actor Brad Pitt and actress Jennifer Aniston attend the 51st Annual Primetime Emmy Awards on September 12, 1999 at Shrine Auditorium in Los Angeles, California. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
Jenn and Brad had been together since 2000 (Picture: Ron Galella Collection via Getty Images)
56th Annual Primetime Emmy Awards - Arrivals
Somehow, Brad mostly escaped the media circus unscathed (Picture: Kevin Winter/ Getty Images)

One Reddit user summed it up perfectly: ‘When two women fight over one guy, that one guy is always gonna be a winner.’

Then came the baby drama. The media latched onto this idea that Jen didn’t want kids, forcing a heartbroken Brad to look elsewhere.

It became a tabloid obsession: Did she choose her career over motherhood? Was she too selfish? Too cold?

Never mind the fact that Aniston had never publicly said she didn’t want children. She was being punished for not fulfilling the role of ‘mother,’ while Brad, who had clearly moved on and started a family with Angelina, was painted as this big-hearted family man.

In a 2022 interview with Allure, Aniston addressed the rumors head-on: ‘And God forbid a woman is successful and doesn’t have a child… 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.’

Even back in 2005, she told Vanity Fair how blindsided she was when photos of Brad and Angelina first surfaced just months after her divorce filing.

Brad Pitt (R) with his son Knox (in arms), daughter Zahara(L) upon his arrival at Tokyo's Narita International Airport in Chiba Province, Japan, . Behind Pitt is US actress Angelina Jolie holding their daughter Vivienne and son Maddox (L) and daughter Shiloh (R center). Pitt is in Japan for the Japan premiere of the film The Curious Case of Benjamin Burton.
BRad would go on to have six children with Angelina (Picture: EPA)
Angelina Jolie and Brad Pitt attend the Cinema for Peace Gala ceremony at the Konzerthaus Am Gendarmenmarkt during day five of the 62nd Berlin International Film Festival on February 13, 2012 in Berlin, Germany. (Photo by Pascal Le Segretain/Getty Images for Cinema for Peace)
Angelina and Brad’s contentious divorce was only recently legally settled (Picture: Pascal Le Segretain/ Getty Images for Cinema for Peace)

‘The world was shocked, and I was shocked,’ she said. ‘I’d be a robot if I said I didn’t feel moments of anger, of hurt, of embarrassment.’

Angelina’s image, meanwhile, was all over the place. On one hand, she was praised for her humanitarian work and her growing family. On the other, she was still being branded as the ‘other woman’ with an ‘agenda.’

It was the classic Madonna-whore complex playing out in real time: She was either a goddess or a seductress, depending on which headline you were reading.

And then there’s Brad Pitt. The man at the center of the entire saga got off with barely a scratch.

He eventually made a comment in Parade magazine in 2011 that seemed to throw shade at his marriage to Jen: ‘I wasn’t living an interesting life myself… I think that my marriage had something to do with it.’

No apology. No real accountability.

His alleged affair with Angelina was often framed as a result of Jen’s ‘failure’ to keep him happy, not as a decision he made as a grown adult responsible for his own actions.

That’s a double standard we see over and over again: when a man cheats, it’s her fault; when a woman cheats, it’s also her fault.

Looking back, the way this triangle was covered says a lot more about us than it does about Brad, Jen, or Angelina. It shows how media narratives lean hard into traditional gender roles, where women are either victims or villains, and men are…well, usually just fine.

In the years since, both Jen and Angelina have opened up about the toll this all took. Jen, in particular, has pushed back against the cultural idea that a woman’s life isn’t full unless she has a husband and kids.

As she told Allure: We are complete with or without a mate, with or without a child.’

This story isn’t just celebrity drama; it’s a case study in how we, as a society, talk about women.

And two decades later, it’s still a reminder of how far we have to go.

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