It has been 18 years since Brad Pitt and Jennifer Aniston‘s shocking split and his affair with Angelina Jolie that shook Hollywood but it’s hard not to look back at the iconic couple and reminisce about what could have been — though we obviously think Aniston deserves better!
The Friends star and Fight Club actor were once the Hollywood “It Couple” before Pitt, now 59, moved on with Jolie, with whom he now shares six children. And, after their lavish 2000 wedding, Pitt gave a rather… unique review of marriage one month in. While pushing through a mob of fans at a London event, Pitt was asked what he loved about being married to Aniston. “It’s fantastic. I love it. Being married means I can fart and eat ice cream in bed. Jen is brilliant. I’m really missing her,” he said, as reported by Us Weekly at the time.
After beginning their romantic relationship in 1998, Aniston and Pitt tied the knot in a stunning beach ceremony that featured 50,000 flowers, four bands and a fireworks display. However, the marriage was not built to last as Pitt and Aniston announced their separation in January 2005. This was amid speculation that Pitt had an affair with Angelina Jolie while filming Mr. & Mrs. Smith, though Aniston and Pitt did attempt to shut those rumors down in their announcement: “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.”
A month after Aniston officially filed for divorce, Jolie and Pitt were photographed on an intimate — and infamous — getaway in Kenya. “I can’t say it was one of the highlights of my year,” Aniston said in a candid Vanity Fair interview after the photos were published. “Who would deal with that and say, ‘Isn’t that sweet! That looks like fun!’? But s— happens. You joke and say, ‘What doesn’t kill you makes you stronger.'” She continued, “I would much rather everyone move on. I am not defined by this relationship. I am not defined by the part [the media is] making me play in the triangle. It’s maddening to me.”
In more recent years, however, Pitt and Aniston have seemed cordial after his divorce from Jolie. The former couple reunited in 2020 for a virtual table read reenacting Fast Times at Ridgemont High to raise money for Sean Penn’s nonprofit CORE (Community Organized Relief Effort.) In an interview with Howard Stern the following year, Aniston said the performance was “fun” and confirmed she’s on good terms with her ex. “Brad and I are buddies, we’re friends,” Aniston said. “And we speak and there’s no oddness at all, except for everyone that probably watched it and was wanting there to be, or assumed there to be,” she continued. “We had fun, and it was for a great cause.”
Before you go, click here to see celebrities who share a famous ex.
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