Yep, it was the era when the Brad Pitt-Angie-Jen saga had us glued to tabloids like it was prime-time TV.
Fans didn’t just watch—they picked sides like it was a personality test: Team Aniston or Team Jolie. It wasn’t just gossip; it was a cultural showdown, shaping how we saw relationships, celebrities, and maybe even ourselves (whether we admit it or not).
Being on Team Aniston meant rooting for marriage, stability, and a grounded kind of glamour. She was America’s sweetheart—the golden girl next door fresh off Friends, who embodied the idea of balancing success and domesticity. On the flip side, Team Jolie was all about embracing the unpredictable, the otherworldly, and that globe-trotting, tattooed energy. Jolie brought an edge to the narrative, making love seem wilder and bigger than the institution of marriage.
But Brad Pitt? Well, nobody really talked about him as much. He wasn’t the one under the microscope—he was the prize. The question wasn’t whether Brad was the right man, but rather which woman was “worthy” of him. It was a classic setup: two women fighting to prove their rightness while Brad sat on the sidelines, already deemed a winner by default.
Fast-forward to today, and it’s clear that neither Jolie nor Aniston ever truly “won” in the way the media framed it. Pitt and Jolie’s marriage ended in 2016, followed by a custody battle that revealed darker layers of their relationship. Aniston, meanwhile, opened up in 2022 about her struggles with infertility during her marriage to Pitt—a reality far removed from the tabloid headlines that painted her as a woman who chose career over kids.
Looking back, this love triangle wasn’t just about Hollywood romance but societal expectations of women. The media pit them against each other, using motherhood and career success as weapons to measure their worth. In the end, Pitt walked away with his image intact, while Aniston and Jolie were left to navigate a narrative that never really let them win.
So, which side were you on back then? And more importantly, did it ever really matter?
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