For over 20 years, America’s had a full-on obsession with Brad Pitt and Jennifer Aniston’s relationship—from their status as America’s golden couple through their divorce and relationships with other people to their current status as friends who seem to get along just fine, thank you very much.
Our collective passion was reignited during the 2020 awards season as Pitt and Aniston crossed paths at the Golden Globes and SAG awards, where they both were nominated—he for Once Upon a Time…in Hollywood and she for The Morning Show. We all basically lost our minds when we saw them embrace backstage, but how did we get here?
Let’s take a look back at the major moments, from when it all began back in the ’90s to now.
1998: Their story begins. You’d be hard-pressed to find two people more famous in the late ’90s than Pitt and Aniston. He was a gorgeous movie star, and she was America’s Sweetheart after being skyrocketed to mega-fame for her role as Rachel on Friends. In the world before a million channels and streaming platforms, around 30 million people were watching Aniston’s show every week. So when these two got together, it was a big deal.
In true Hollywood fashion, they were set up by their agents, and Aniston told Diane Sawyer it was a done deal from that moment. “We both [knew] on our first date,” she said, per Us Weekly.
1999: By the Emmys in 1999, they start hitting red carpets together, feeding the public frenzy. They even got on stage together at a Sting concert.
July 29, 2000: Brad and Jen say “I do” in a massive Malibu wedding that had helicopters circling the venue to try to capture any moment they could. The couple then released one iconic black-and-white photo to the press. “We just wanted to keep it special. Keep it ours,” Pitt later said. People reported there were 200 guests, 50,000 flowers, four bands, and a gospel choir. Guests included Friends stars Courteney Cox, Lisa Kudrow, Matthew Perry, David Schwimmer, and Matt LeBlanc along with celebs like Cameron Diaz, Edward Norton, and his then girlfriend Salma Hayek.
January 7, 2005: And then, just like that, the fairy tale is over: “We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration,” Pitt and Aniston say in a joint statement to People at the time. “We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.”
April and May 2005: The Brangelina era begins. Pitt had already filmed Mr. and Mrs. Smith with Angelina Jolie in 2004 and soon their relationship would become a focal point in the press. He was soon photographed with Jolie and her young son, Maddox, in Kenya, sparking rumors. The two actors also starred in a photo shoot for W titled “Domestic Bliss”, where they portrayed a happy family life.
September 2005: Aniston appears on the cover of Vanity Fair and gives one of her most famous interviews. “It was extremely hurtful to Jen that he was seen with another woman so quickly after they were separated,” her friend Andrea Bendewald said in the story.
“A man divorcing would never be accused of choosing career over children,” Aniston said of the accusations that her not wanting a child caused the split. “That really pissed me off. I’ve never in my life said I didn’t want to have children. I did and I do and I will! The women that inspire me are the ones who have careers and children; why would I want to limit myself? I’ve always wanted to have children, and I would never give up that experience for a career. I want to have it all.”
Of the W shoot she said, “Is it odd timing? Yeah. But it’s not my life. He makes his choices. He can do—whatever. We’re divorced, and you can see why.” And then she uttered this famous line: “There’s a sensitivity chip that’s missing.”
October 2005: Brad Pitt and Jennifer Aniston’s divorce is finalized
December 2008: Aniston gives another high-profile interview about Jolie and Pitt, this time to Vogue. She references an interview Jolie also gave to Vogue, where she implied she and Pitt fell in love on the set of Mr. & Mrs. Smith. (“I think we found this strange friendship and partnership that kind of just suddenly happened. I think a few months in I realized, ‘God, I can’t wait to get to work,’” Jolie said.)
“There was stuff printed there that was definitely from a time when I was unaware that it was happening,” Aniston told Vogue about Jolie’s interview. “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.”
September 2014: Pitt and Jolie marry.
August 2015: Aniston and actor Justin Theroux tie the knot.
September 2016: Pitt and Jolie file for divorce.
February 2018: Aniston and Theroux announce they’re separating.
February 2019: Pitt attends Aniston’s 50th birthday party in Los Angeles—thus beginning the “exes who are now just good friends” era. People, naturally, started shipping them.
December 2019: Aniston throws a Christmas party, and guess who attends? Pitt. Again, just as a friend. “They have been in touch a few times since her birthday and are keeping it friendly,” a source told People, earlier adding, “The annual tree-trimming party is always Jen’s favorite to host. She loves Christmas. As usual, a large group of friends attended.”
January 6, 2020: We begin our series of awards season run-ins. First, the Golden Globes, where Pitt cracks this joke during his acceptance speech: “I wanted to bring my mom, but I couldn’t because any woman I stand next to, they say I’m dating.” Aniston laughs, and the internet goes wild.
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Earlier in the evening, Entertainment Tonight asked Pitt if he’d be cool running into Aniston, to which he says, “I’ll run into Jen. She’s a good friend.”
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We then learn from E! News that the two had a friendly meet-up at a Globes after-party. “They said hello very quickly,” a source said. “Jen arrived after Brad. It was brief, but [they] were very cordial and friendly and seemed happy to be there. They approached each other once they saw each other inside and looked happy as they started to hug and say hello. Jen whispered something to Brad, but it wasn’t in an affectionate way. They both didn’t seem like they wanted to make a big deal about being together in the same room although it was a private party. They were trying to be low-key. Brad left shortly after and didn’t stay at the party long.”
January 19, 2020: After both win big at the SAG Awards, Aniston and Pitt share a [friendly moment] backstage. They have their photos taken together publicly for the first time in years.
During his acceptance speech, Pitt made a joke about marriage, which Aniston laughed at:
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The photographer who snapped the pics of Pitt and Aniston at the SAGs, Emma McIntyre, gave some details about what happened to People.
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“[They were both backstage] doing the circuit of awards press,” she told the publication. “Jennifer had just signed some posters for SAG and was about to walk the press line. I was running back and forth between the two backstage areas and had just taken some photos of Jennifer. I was about to leave when I saw Brad coming down the hallway and sensed there would be a photo-worthy moment.”
She continued, “He called out ‘Aniston!’ and she turned around and they embraced and congratulated each other. It was a moment of two accomplished people at the top of their game, acknowledging each other’s successes and genuinely seeming happy to see one another…. The moment was really touching, and you could sense the respect between two people who have known each other 20-plus years and are both outstanding in their field.” Aniston later said Pitt watching her acceptance speech from backstage was "sweet."
Courteney Cox, Aniston's Friends co-star, "liked" several social media posts about Brad and Jen's reunion. Fan pandemonium reached a fever pitch after the SAGs, with several people think Aniston and Pitt's similar hairstyles were a sign they were getting back together.
After the SAGs, reports came out alleging Pitt had "apologized" to Aniston for "many things" in their relationship.
February 9, 2020: We learn from Page Six that Pitt and Aniston reportedly had a run-in at talent manager Guy Oseary’s famous Oscars after-party. (Pitt hilariously wore a name tag to the Oscars days prior.) “We’re told there was no sizzle this time around,” the paper wrote. “Spies say that, while Aniston congratulated Pitt on his win, they didn’t hang out long.”
