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2000: Brad Pitt And Jennifer Aniston
From the moment Brad Pitt and Jennifer Aniston first started dating in 1998, the world took notice. At the time, Aniston was right in the middle of her career on Friends, and Pitt was already well established as a film actor (as well as being a heartthrob). They married in 2000, and shocked the world when they announced their separation in 2005, especially with rumors that Pitt had an affair with his next wife, Angelina Jolie.