2. Brad Pitt
Will Colbert – “The One With the Rumor” – S8E9
At the time, it was pretty obvious how movie star Brad Pitt ended up doing a guest spot on Friends. After all, he was married to Jennifer Aniston, one of the show’s big stars. Playing off of this obvious act of nepotism, Pitt played a character named Will Colbert, a friend of Ross and Monica’s from high school who despised prom queen Rachel Green.
Like Monica, Will was overweight as a teen; like Ross, he was a geek in high school. Although Monica and Ross have fond memories of their friendships with Will Colbert, Rachel doesn’t even remember him. She certainly doesn’t remember picking on him and making his high school years miserable. If she had, she probably would not have attempted to flirt with him when he shows up at Monica’s for Thanksgiving dinner. (She wasn’t alone; Phoebe developed quite the crush during Will’s brief visit to New York.)
Not only is Rachel unaware that Will was the target of her “mean girl” behavior, she’s also unaware that Ross was once a co-founder of the I Hate Rachel Green Club until Will rats him out. He also tells on Ross for being behind the rumor that Rachel had both male and female genitalia, a rumor that even made it as far as Chandler’s high school in another town. Will is shocked to discover that Ross dated Rachel and having a child with her. He is, however, proud to see that his friend isn’t marrying Rachel, despite of the fact that she’s having his child.
Looking back, it was fun to see Pitt and Aniston, partners in real life, playing enemies on the show. Pitt rarely appeared in television roles once he became famous for his work in movies like Fight Club and Se7en. In fact, he’s only appeared in two television series since then. He provided the voice of Patch Boomhauer in an episode of King of the Hill and in a documentary mini-series titled Freedom: A History of Us in 2003.