When Jennifer Aniston and Brad Pitt Flaunted Her Engagement Ring at a Sting Concert Back in 1999

A 1999 Sting concert became famous not for the obviously stellar performance by Sting but for a dazzling couple that took the stage that night: Jennifer Aniston and Brad Pitt. While there is no definitive date for Pitt's proposal to Aniston, the couple did hit the stage at a Sting concert on November 29, 1999, to show off the bride-to-be's new engagement ring. Pitt even sang, “We’re going to Vegas, we’re gonna get wed / So fill her up, son, don’t be staring / Yeah, that’s a real diamond she be wearing.” 

It's worth noting that the ring, which included a number of round-cut diamonds, was said to cost $500,000. The actor from The Big Short apparently collaborated with designer Silvia Damiani to create Jen's engagement ring. The central diamond is surrounded by smaller diamonds that spiral around it as a symbol of eternity. 

The Murder Mystery actress met Brad in 1998 and married him in 2000. Fans were startled when the couple, who were the most famous couple in Hollywood at the time, divorced in 2005. Their split came amid allegations that the Fight Club actor cheated on Aniston with Angelina Jolie, his Mr. & Mrs. Smith co-star, whom he began dating shortly after, per Life&Style Magazine.

Although Jen's marriages did not work out, she said in an interview that she did not consider them failures. “My marriages, they’ve been very successful, in my personal opinion,” Aniston once told Elle magazine. “And when they came to an end, it was a choice that was made because we chose to be happy. And sometimes happiness didn’t exist within that arrangement anymore.”

Jennifer stated in the interview that she would never stay in a relationship simply to escape being single. “This is our one life, and I would not stay in a situation out of fear,” she explained. “Fear of being alone. Fear of not being able to survive. To stay in a marriage based on fear feels like you’re doing your one life a disservice. When the work has been put in and it doesn’t seem that there’s an option of it working, that’s OK. That’s not a failure.”

“It’s a glass-half-full kind of thing. Always being open. Allowing myself to feel what I feel,” the Dumplin' actress said of her life. “What brings me happiness? I have a great job. I have a great family. I have great friends. I have no reason to feel otherwise.”

Brad Pitt has also repeatedly praised his ex-wife, who he still considers to be a very close friend. “Jen is an incredibly giving, loving and hilarious woman who remains my friend. It is an important relationship I value greatly,” Brad said during an interview in 2011. “The point I was trying to make is not that Jen was dull, but that I was becoming dull to myself — and that, I am responsible for,” he explained.