Celebrity relationships and friendships are a rare breed. These famous faces have their lives played out in front of the masses, whether it’s the good, the bad, or the straight-up shady. In Elite Daily’s new series, It’s Complicated, we’re highlighting the biggest celebrity “feuds” that took over Hollywood and dominated our Sunday brunches for weeks on end. We’ll take a deep dive into the lives and social media feeds of our favorite stars and dissect what happened in front of the camera, what went down behind the scenes, and everything you might have missed in between.
It's been nearly 15 years since Jennifer Aniston and Brad Pitt divorced. Despite the cheating rumors that plagued their marriage and the fact both Aniston and Pitt moved on with other people after their divorce, there are still shippers out there who believe the former flames are destined to reunite. It's understandable to some degree. Even after all of the drama, Aniston and Pitt somehow managed to maintain a friendship and are in a good place in 2020 – which is great for them, considering the number of friends and acquaintances they have who run in the same circles. Hollywood is really small, so the A-List people Jennifer Aniston and Brad Pitt have in common always face the prospect of running into each other. Thankfully, when they inevitably do, they seem to be able to do so in peace.
1. Angelina Jolie
Before Aniston and Pitt announced their split in January 2005, rumors Pitt cheated on Aniston with his Mr. & Mrs. Smith co-star Angelina Jolie were all over the tabloids.
In a joint statement announcing their divorce, Aniston and Pitt denied the rumors of infidelity. But a month later, before their divorce was even finalized, Pitt was photographed with Jolie and her son Maddox on a beach in Kenya, reviving the cheating rumors.
In September 2005, Aniston revealed the one time she spoke with Jolie in an interview with Vanity Fair. "It was on the lot of Friends — I pulled over and introduced myself. I said, ‘Brad is so excited about working with you. I hope you guys have a really good time,'" she said, before revealing that after Pitt met Jolie, "He was gone."
Jolie later admitted she fell for Pitt while filming Mr. & Mrs. Smith.
"Because of the film we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened," she told Vogue in January 2007. "Whether it was shooting a scene or arguing about a scene or gun practice or dance class or doing stunts — anything we had to do with each other, we just found a lot of joy in it together ... And it took until, really, the end of the shoot for us, I think, to realize that it might mean something more than we’d earlier allowed ourselves to believe."
As she told Vogue in December 2008, Aniston found Jolie's remarks about falling for her then-husband inappropriate.
“There was stuff printed there that was definitely from a time when I was unaware that it was happening. 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."
Apart from their one meeting on the lot of Friends, Aniston and Jolie understandably don't have many public run-ins with one another. Pitt and Jolie, however, will always be connected for the sake of their six children. As Jolie told Good Morning America in 2017, they "will always be a family."
2. Justin Theroux
After her divorce from Pitt, Aniston also moved on with someone new, wedding actor Justin Therox in August 2015.
Many rumors involving Aniston's past relationship with Pitt plagued her and Theroux's relationship, and they were dragged into stories surrounding Pitt and Jolie purely by association. After Pitt and Jolie announced their separation, Theroux told Business Insider in September 2016 it was “nonsense” his then-wife’s name was being thrown into the mix.
"There are bigger things to b*tch about," Theroux said. "It's shocking how much bandwidth things can take up when there are far more important things going on in the world."
He did empathize with Pitt and Jolie's kids, saying, "As a child of divorce, all I can say is that's terrible news for those children, and that's all you can really say. It's boring to sort of comment on anything else. People are having a bad time — that's horrible."
In February 2018, Aniston and Theroux called it quits — though, it was an amicable divorce. In September 2018, Theroux told the New York Times he and Aniston were still friends and the decision to divorce was "mutual and lovingly made."
3. George Clooney
George Clooney is one of Pitt's closest friends. The two worked together on 2001's Ocean's Eleven and have been tight ever since, going on to star in four more movies together: Confessions Of A Dangerous Mind, Ocean's Twelve, Ocean's Thirteen, Burn After Reading.
Considering Pitt was married to Aniston while his friendship with Clooney blossomed, it makes sense Clooney also has a relationship with her, too. Together, the trio attended various Hollywood events, and even vacationed together in Italy in the summer of 2004.
Thankfully, it looks like Brennifer both got to keep Clooney after the divorce. In February 2019, Clooney and his wife Amal attended Aniston's 50th birthday party at West Hollywood's Sunset Tower, and Pitt was also in attendance. So, while the trio may not be vacationing together anymore, Clooney, Aniston, and Pitt can still hang out together in group settings.
4. Courteney Cox
Friends may have ended in May 2004, but Aniston and her co-star Courtney Cox are still as tight IRL as their characters were on the show.
The besties are constantly hanging out with each other at events. for example, Cox was also in attendance at Aniston's 50th birthday soirée and Aniston showed up at Cox's 55th birthday party in June 2019.
Cox and Pitt are certainly acquaintances as well. Besides being married to her BFF at one point, she worked with him when he guest-starred on Friends in 2001 as Monica's old high school friend.
There was never any reported beef between Aniston's ex-husband and Cox after Brennifer's divorce, but she did come to Aniston's defense when asked about Aniston's involvement in Pitt and Jolie's split in September 2016 and kept things 100% diplomatic.
“I feel like we’re exacerbating it by even talking about it. It’s not about her,” Cox told Entertainment Tonight in September 2016.
5. Reese Witherspoon
Aniston currently stars on Apple TV+'s The Morning Show alongside Reese Witherspoon, but the two go way back. Witherspoon guest-starred on Friends twice in 2000 as Aniston's character's little sister, Jill.
It seems like things are pretty cool between Aniston, Witherspoon, and Pitt these days. When actor Mindy Kaling posted a dashing throwback photo of Pitt on Instagram on Sept. 25, 2019, Witherspoon couldn't help but gush in the comments section, writing "Oh dear" along with a heart-eyes emoji (CommentsByCelebs caught all the action).
Aniston didn't seem to be bothered by the harmless comment. She and Witherspoon even shared a quick laugh at the 2020 Golden Globes on Jan. 5 when Pitt made a joke about not taking his mom as his date to the show because everyone would think they were dating. Check it out at the 2:12 mark below.
Brennifer may no longer be an item, but they've moved past their complicated history to form a pretty awesome friendship. In the end, whether the people they have in common were Pitt or Aniston's friend first, everyone is able to keep it cordial when they cross paths.