Gwyneth Paltrow and Winona Ryder
Gwyneth Paltrow and Winona Ryder were nearly inseparable in the '90s — they were dating BFFs Ben Affleck and Matt Damon, respectively — but cut ties in 1998 when Gwyneth reportedly stumbled upon the script for Shakespeare in Love lying around Winona's home. Gwyneth is said to have asked to audition for the role, and as we all know, she landed it, and went on to win an Oscar.
Things came to a head again in 2009 after Gwyneth launched her now-famous website, Goop. In an early article, she addresses a former friend that many speculate to be Winona, saying, "Back in the day, I had a 'frenemy' who, as it turned out, was pretty hellbent on taking me down." She went on to write: "I restrained myself from fighting back. I tried to take the high road. But one day I heard that something unfortunate and humiliating had happened to this person. And my reaction was deep relief and happiness."