Who: Oscar-winning producer and actor Brad Pitt, 55, and Golden Globe and Emmy-winning actress Jennifer Aniston, 49.
How They Met: Aniston and Pitt initially crossed paths in 1994 when Friends was just beginning, but it wasn’t until ’98, after their respective splits from Tate Donovan and Gwyneth Paltrow, that their managers set them up on a date. Aniston later told Diane Sawyer that she knew “on the first date” that he was the one for her. Five months later, they were engaged. And in July 2000, the very tan and financially stable All-American sweethearts wed in a private ceremony in Malibu. Important aside: People reported that Brad and Jen got matching “‘brother-and-sister’ blond highlights” ahead of the ceremony, so please keep that strange image in your mind as you read this.
When They Peaked: Though they were literal Hollywood royalty, Brad and Jen both deigned to attend an event sponsored by Coors Light, and when Brad was all like, “I refuse to trim my out-of-control beard, plus I’m going to wear a ridiculous straw hat, a sheer yellow shirt I got at a thrift store on the way here, and an American flag patch on my too-faded jeans,” Jen still agreed walk the carpet with him. That’s love.
Why We Loved Them: Jen once called Brad “the most fun I’ve ever had,” and from early photos of the two, that much is evident.
However, as anyone who’s visited a grocery store checkout line since 2005 surely knows, that fun did not last ‘til death do us part.
The Breakup: When it comes to the split that literally rocked the nation (we had t-shirts and everything), there are two main schools of thought: 1) Angelina Jolie and Brad Pitt hooked up on the set of Mr. and Mrs. Smith, ending the latter’s marriage to Aniston; 2) Aniston and Pitt’s split had nothing to do with a third-party — they had their own insurmountable issues. According to Jen herself, it sounds like their separation actually straddles the line between the two.
Though the media insisted for years that Pitt and Aniston were some sort of golden-tressed power couple immune to the pressures of Hollywood, both parties have since admitted that things were not as picture-perfect as meets the eye.
In a 2011 interview, Pitt reminisced about his past, telling Parade, “It became very clear to me that I was intent on trying to find a movie about an interesting life, but I wasn’t living an interesting life myself. I think that my marriage [to actress Jennifer Aniston] had something to do with it. Trying to pretend the marriage was something that it wasn’t.”
In her first major post-split interview, Aniston told Vanity Fair, “We were put on a pedestal, but we were just a couple like anybody else.” Though she professed her love of the solidarity that comes with marriage, and the idea that you can “re-meet, reconnect” with your spouse when times are hard, she said Pitt shared a different view. “We believe in different things, I guess. You can’t force a relationship, even if it’s your view of how you would like it to be conducted,” she admitted.
That being said, Jen is still grateful for the experience of her first marriage. “I still feel so lucky to have experienced it,” she said, “I wouldn’t know what I know now if I hadn’t been married to Brad. I love Brad; I really love him. I will love him for the rest of my life. He’s a fantastic man. I don’t regret any of it, and I’m not going to beat myself up about it. We spent seven very intense years together; we taught each other a lot — about healing, and about fun. We helped each other through a lot, and I really value that. It was a beautiful, complicated relationship. The sad thing, for me, is the way it’s been reduced to a Hollywood cliché — or maybe it’s just a human cliché. I have a lot of compassion for everyone going through this.”
As for the beautiful, Oscar-winning elephant in the room? Jen chooses to believe that Jolie and her former husband began their romantic relationship after Pitt and Aniston had split. “There’s a lot I don’t understand, a lot I don’t know, and probably never will know, really,” she confessed, noting, “At this point, I wouldn’t be surprised by anything, but I would much rather choose to believe him.”
That’s not to say the whole ordeal didn’t hurt (like hell). A few years after the explosive Vanity Fair article was published, Aniston opened up about quotes Jolie had given Vogue in early 2007, telling the publication that she realized “‘God, I can’t wait to get to work,’” a few months into her and Pitt’s working relationship.
“There was stuff printed there that was definitely from a time when I was unaware that it was happening,” Aniston told Vogue. “I felt those details were a little inappropriate to discuss. That stuff about how she couldn’t wait to get to work every day? That was really uncool.”
Where They Are Now:
After finalizing his divorce from Aniston, Pitt adopted Jolie’s son, Maddox, and daughter, Zahara, in early 2006. The couple welcomed their first biological child, Shiloh, in May 2006, and adopted then-3-year-old son Pax in mid-2007. The Jolie-Pitts capped off their massive brood in July 2008 after welcoming biological twins Knox and Vivienne in the South of France.
Though they’d been romantic partners for nearly 10 years, it wasn’t until 2014 that Brad and Angelina officially wed. Two years later, in September 2016, the universe’s collective jaw dropped when it was announced that Brangelina had called it quits.
More than two years later, Pitt and Jolie are still in the throes of a custody battle, which is reportedly the main reason their divorce has yet to be finalized.
On the professional front, things have been a tad more stable. Brad had an incredible year in 2014 when he (on behalf of production company Plan B, which he once co-owned with Aniston) won both an Emmy for The Normal Heart and an Oscar for 12 Years a Slave. Though it seems Pitt is more focused on producing than acting these days, he’s starring in two major films in 2019: Quentin Tarantino’s Once Upon a Time in Hollywood and James Gray’s Ad Astra.
Aniston began dating her second husband, actor Justin Theroux, after reconnecting on the set of Wanderlust in 2010 (they previously met on the set of Tropic Thunder in 2007). Theroux proposed in 2012, and they wed three years later in 2015.
After two-and-a-half years of what we’d thought (or at least hoped) was wedded bliss, Jen and Justin announced their separation.
Like Pitt, Aniston also had an impressive 2014. The Friends star proved her dramatic chops with a fiery performance in Cake, which earned her a Golden Globe nomination (SHE. WAS. ROBBED).
After a brief hiatus between projects, Jen is coming back with a vengeance in the coming months. Her latest film, Dumplin,’ hits Netflix on December 7, which will be followed by a reunion with Just Go with It co-star Adam Sandler in Murder Mystery, and Aniston’s long-awaited return to television alongside Reese Witherspoon and Steve Carell.