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1. Jenifer Aniston and Brad Pitt
One of the most famous Hollywood couples unsurprisingly had one of the most infamous divorces. Jennifer Aniston and Brad Pitt met in 1994 because their managers were friends. However, the two didn’t go on their first date until 1998. The Hollywood heartthrobs made their official debut at the Emmy Awards a year later. Fast forward to 2000 and the two married during a lavish ceremony in Malibu. All seemed well until Brad Pitt met Angelina Jolie on the set of 2004’s “Mr. and Mrs. Smith”. Pitt and Aniston’s divorce was finalized a year later, due to rumors of Pitt’s infidelity with Jolie.