JENNIFER ANISTON & BRAD PITT – 5 YEARS

Jennifer Aniston and Brad Pitt were a big thing back in the 90s, long before there was Brangelina. The Friends alum and The Curious Case of Benjamin Button star shared seven wonderful years from 1998 to 2005 as a couple. Brad met Jen through their respective talent managers. After their first date turned out to be successful, the two hit it off quickly. The couple debuted their relationship to the public in a classic Hollywood style. In November of 1999, they crashed the stage during a Sting concert to announce to the world their engagement. It did not take long for the couple to pour out investments into the wedding of their dreams. Brad and Jen exchanged their vows at a grand Malibu wedding in July 2000. It seemed like everything was going on perfectly for the celebrity couple.

However, in January of 2005, the two decided to separate. Though it’s good to know that they have remained good friends after all these years.