16 of the Most Iconic Celebrity Couple Moments in Pop Culture History

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Brad Pitt's guest appearance on Friends


Before there was Brangelina, there was Brad and Jen. In the late nineties and early aughts, Brad Pitt and Jennifer Aniston were Hollywood's golden couple. The two biggest stars at the time got together to define what #CelebrityCoupleGoals really meant. So it was a BIG DEAL when Brad made a guest-star appearance on Jen's show, Friends. But he wasn't playing her love interest. In fact, his character was friends with Ross and Monica years ago, who, like Monica, lost a lot of weight as an adult. Brad and Jen's characters clash because of the way she treated him in high school, and he was the co-founder of the “I Hate Rachel Green” club — with Ross! Seeing the two snipe at each other when you know they were in love IRL is classic.