8. Jennifer Aniston & Brad Pitt
Jennifer and Brad were America’s sweetheart couple in the early 2000s. Their picture-perfect marriage ended in 2005, amid rumors of Brad’s growing closeness to Angelina Jolie. The split sparked endless headlines, magazine covers, and a cultural obsession with Jennifer’s heartbreak.
Despite it all, Jen handled the breakup with grace and resilience. It remains one of the most iconic and heartbreaking celebrity love stories ever.