Pitt and Aniston met in 1998 after being set up on a blind date by their agents. The two tied the knot by 2000 before splitting five years later.

Back in the late ‘90s, Gwyneth Paltrow and Brad Pitt were engaged.

Brad Pitt and Jennifer Aniston were such an iconic couple that people continue to ponder the reason for their 2005 divorce even decades later. The consensus is that the "F1" star cheated on his first wife with his second,