Brad Pitt and Angelina Jolie were one of Hollywood's most iconic "it" couples. The former pair first met in 2003 while portraying the role of husband and wife in the film Mr. & Mrs. Smith. Jolie was enjoying being a single mother, and Pitt was still married to Jennifer Aniston (the two later split in 2005). Looking back, Jolie recalled to Vogue that it wasn't really love at first sight; she and Pitt just made a good team.

Even now that they are separated, Pitt and Jolie still bring their kids to the same destinations.

All relationships have their ups and downs, especially in Hollywood, but Brad Pitt and Angelina Jolie's relationship timeline is especially fascinating. It was a scandal when the couple got together, but they seemed like a solid unit for over a decade…at least on the outside. So, when the couple filed for divorce. As a result, Brad Pitt has admitted to feeling depressed and alone since his divorce from Angelina.

So, was the divorce really the right choice for the pair? Did Jolie feel happy about winning Pitt over from Aniston?

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Angelina Jolie And Jennifer Aniston Had A Similar Dating History

Angelina Jolie and Jennifer Aniston are undoubtedly two of Hollywood's biggest actresses. While the duo may have a common link when it comes to being married to Brad Pitt, the two ladies have many other interesting facts to their name than being attached to the Hollywood actor.

While Aniston shot to fame with her stint on the famed sitcom Friends which aired between 1994 and 2004, Jolie has been an acclaimed actress ever since her performance in Academy Award-winning film Girl Interrupted.

The two actresses have often been compared by fans due to their Pitt connection. Jennifer and Brad were married for almost five years after tying the knot in Malibu in 2000. As for Jolie, the actress married Brad in 2014 and eventually, the couple was declared divorced legally in 2019.

Over the years, both Jennifer and Angelina have been pitted against each other as the famous exes of Pitt.

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Angelina Jolie And Jennifer Aniston Have Both Expressed Views About Each Other

While speaking to Vogue in 2007, Jolie spoke about the start of her and Brad's relationship when she mentioned his marriage to Aniston saying, "I didn’t know much about exactly where Brad was in his personal life. But it was clear he was with his best friend, someone he loves and respects. And so we were both living, I suppose, very full lives."

Aniston had recalled her first meet with Jolie in interaction with Vanity Fair where she mentioned, she spoke to Angelina ahead of her film with Pitt and said, "Brad is so excited about working with you. I hope you guys have a really good time."

The actress also revealed that during the filming of the movie, she would look forward to heading to the sets and working with Brad.

"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. I think a few months in I realized, God, I can’t wait to get to work. 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 a lot of real teamwork. We just became kind of a pair," Angelina explained.

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Brad Pitt And Jennifer Aniston's Divorce Is Still In The Headlines

It has been over 15 years since we last saw Jennifer Aniston and Brad Pitt as a couple, however their romance is definitely one for the history books. Although the couple was only together for seven years (and married for five!), their A-list relationship did not end with their divorce in 2005.

Between their one million dollar wedding, his guest appearance on Friends and their iconic reunion in 2020, there are a few things to know about Brad Pitt and Jennifer Aniston's relationship. Brad Pitt and Jennifer Aniston first met in 1994, but they didn't begin dating until 1998. He later proposed to Jennifer in 1999, and they had their wedding the following year. After five years of marriage, the couple announced their split in early 2005. Brad went on to date and wed actress Angelina Jolie while Jennifer wed Justin Theroux.

They both went on to divorce their spouses and have since remained close friends.