The episode, titled "The One with the Rumor," originally aired on November 22, 2001. Pitt played Will Colbert, a former overweight high school class of Monica, Ross, and Rachel. Will has harbored a decades-long grudge against Rachel (Aniston, Pitt’s then-real-life wife) because she cruelly mocked him at a prom after-party. His revenge? Co-founding the "I Hate Rachel Green Club" with Ross—and starting a vicious rumor that Rachel was a hermaphrodite.
Fun fact: Pitt won an Emmy for Outstanding Guest Actor in a Comedy Series for this role—his only Primetime Emmy to date. friends episode with brad pitt
Beyond the laughs, "The One with the Rumor" works because it fits seamlessly into Friends lore. It expands Ross and Monica’s high school history, gives Rachel a rare moment of being the accidental villain, and introduces a character so delightfully absurd that you almost root for his grudge. The episode, titled "The One with the Rumor,"