Brad Pitt’s guest appearance as Will Colbert — a former high school class of Monica, Ross, and Rachel — is comedy gold. Pitt plays a bitter guy who co-founded the “I Hate Rachel Green” club with Ross back in the day. The episode brilliantly builds to the hilarious reveal that Will’s hatred for Rachel stems from her supposedly spreading a rumor that he was “gossipy” (which he takes as a devastating insult to his masculinity).

In this episode, Brad Pitt plays a charming and handsome coffee shop owner who opens a new cafe across the street from Central Perk. The gang is immediately drawn to the shop's trendy vibe and becomes regulars. However, things get complicated when Joey starts to develop a crush on Brad, much to the amusement of the rest of the group. Meanwhile, Monica tries to impress Brad with her culinary skills, and Chandler attempts to flirt with him (with disastrous results).

Here’s a good review of The One with the Rumor (Season 8, Episode 9), the Friends episode featuring Brad Pitt.

This iconic Thanksgiving episode centers on the arrival of Will Colbert (Brad Pitt), an old high school classmate of Monica, Ross, and Rachel. While Monica is thrilled to see him, the reunion turns awkward when it is revealed that Will absolutely loathes Rachel Green. Meanwhile, Joey attempts to eat an entire turkey to prove a point, and Phoebe encourages a hesitant Chandler to spend time alone with Monica to practice being a husband.

This is widely considered one of the best Thanksgiving episodes in the show’s history. Unlike some celebrity guest spots from the early 2000s that feel awkward in hindsight, Pitt’s appearance remains funny because it leans entirely into the joke. The episode understands that the joke isn't just "Brad Pitt is here"—the joke is "Rachel’s real-life husband is pretending to be her high school nemesis."

The plot centers on a Thanksgiving dinner hosted by Monica Geller. Monica invites an old high school friend, Will Colbert, played by Pitt. Will was formerly overweight in high school and has since undergone a significant physical transformation. However, it is quickly revealed that Will harbors a deep, burning hatred for Rachel Green because she was mean to him during their school years.