Best Friend Breakups

Gwyneth Paltrow and Winona Ryder

When Paltrow and Ryder dated Ben Affleck and Matt Damon respectively, the actresses were inseparable in the '90s -- until Paltrow reportedly stumbled upon the script for Shakespeare in Love at Ryder's home. Adding salt to the wound, Paltrow won an Oscar for the role she allegedly stole from her BFF.

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