Jennifer Aniston & Brad Pitt

Jennifer Aniston and Brad Pitt at a Sting concert may be the most “1990s” thing ever, as they were two of the biggest stars of the 90s.  In 1999, they were in New York City celebrating their engagement when they attended the concert.

They dated for around one year prior to getting engaged, although they initially tried to keep the relationship a secret. Despite their efforts, Aniston and Pitt were caught together at the Tibetan Freedom Concert. There have been plenty of rumors of the two reuniting after Pitt’s divorce from Angelina Jolie. While it would make a lot of fans happy, it has yet to happen.