2000: Brad Pitt and Jennifer Aniston

Brad Pitt and Jennifer Aniston became the hottest item in 2000 when their agents set the two up on a date. They did keep things low-key as much as they could, but it was tough since Brad was one of the biggest names in Hollywood while Jennifer was considered America’s sweetheart. It was in 1999 that they made their relationship public, which made their fans delirious with joy. We have to say that they really looked great together.

The two put some serious investments into their wedding, which was quite lavish, especially since it was held in Malibu. There was a media circus back then, which was not surprising given that this was the wedding of the year! Though the couple broke up, they remain friends until today. There were many who wanted them to get back together, sure, but so far neither one is making a move at all.