Pitt met Angelina Jolie in 2004 on the set of their spy film Mr and Mrs Smith.
It didn't take long for speculation on the nature of their relationship to kick off; while they denied anything was happening at the time, the stars later admitted they "fell in love" during filming.
In July 2005, Pitt and Jolie made it official in the most Hollywood way possible: with a magazine spread titled 'Domestic Bliss'.
This sparked enormous controversy, and a very 2005 media narrative of 'Team Jen vs Team Ange' was born. (Conveniently, Pitt's role in the saga was largely ignored!)
Even Aniston weighed in, saying a "sensitivity chip" had been missing in regards to the publication of the magazine spread, which featured photos of Pitt and Jolie as a happy couple.
"I can't say it was one of the highlights of my year," the Friends star admitted in an interview later that year.
"Who would deal with that and say, 'Isn't that sweet! That looks like fun!'? But ... you joke and say, 'What doesn't kill you makes you stronger.'
"I would much rather everyone move on. I am not defined by this relationship."
Just six months later, in January 2006 – a year after Pitt's split from Aniston was confirmed – the couple announced they were expecting their first child together.
This year, two decades on, the couple has finalised their acrimonious divorce after eight years.
English (US) ·