#35: Sandra Bullock and Jesse James

Duration of Relationship: 6 years (2004–2010)

The 2010 breakup between Sandra Bullock and Jesse James shocked the world, coming on the heels of her Oscar win for The Blind Side. Just days after her triumph, revelations of James’ infidelity surfaced, with multiple women claiming to have had affairs with him.

Bullock, blindsided by the scandal, swiftly filed for divorce, ending their five-year marriage. The couple had been adopting a child together, which Bullock chose to continue as a single parent. The betrayal devastated Bullock personally and left a lasting impact on her public image.