The most tragic Hollywood break up was, undoubtedly, Jennifer Aniston and Brad Pitt's divorce. Fans thought that nothing could tear them apart. But, then along came Angelina Jolie, who fell in love with Pitt while they were on set filming "Mr. & Mrs. Smith". In the meantime, Angelina and Brad have also filed for divorce. Jennifer Aniston went on to marry Justin Theroux in 2015, but seperated from him in early 2018.