16 Unfortunate Celebrity Friend Breakups
frenemies winona gwyneth jpg
2 of 16
Back in the late ‘90s, Gwynnie and Winona Ryder were besties and dating fellow besties, Ben Affleck and Matt Damon. The foursome was inseparable. Rumor has it, Winona had the script to “Shakespeare In Love,” Gwyneth saw it at her house and snatched it up, eventually stealing the part from underneath her nose. She went on to win the Oscar. Winona and Gwyneth haven’t been friends since.