When: 2004
It's difficult to say whether or not these two hooked up. They definitely worked together in 2004 on Alexander. In addition to rumors here and there in the media, a book called Brad Pitt And Angelina Jolie: The True Story, written by US biographer Jenny Paul, who listed Jolie's close friend Texas Terri as a source, alleged that the two dated for four months, but eventually broke up because of Farrell's heavy drinking. Now that he's sober at least he can take solace in knowing that his addiction saved him from having to raise six kids.
Smash Probability:

Also Watch