A Complete Timeline of Brad Pitt and Angelina Jolie's Relationship and Divorce

By Stuart Wolf - Jul 9, 2025

This article appeared in oklaugh.com and has been published here with permission.

Hunky Hollywood heartthrob Brad Pitt had it all. He was the most famous film star on the planet and married to beloved actress Jennifer Aniston. Then, he fell in love with Angelina Jolie. They had six children and married at their French château. But then, their lives changed forever when Angelina divorced Brad. So, strap yourselves in for a complete timeline of Brad Pitt and Angelina Jolie's relationship and divorce...

Brad's Origin Story

William Bradley Pitt was born in Shawnee, Oklahoma, on December 18th, 1963, to trucker William Alvin Pitt and school counselor Jane Etta Pitt. After attending Kickapoo High School and the University of Missouri, Brad moved to Los Angeles, took acting lessons, and worked odd jobs.

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After bit parts in films, cop shows, and sitcoms, Brad landed the role of cowboy hitchhiker J.D. in Ridley Scott's Thelma and Louise. After showing off his abs and those love scenes with Geena Davis, hunky Brad Pitt was a star.

Angelina's Backstory

12 years later, on June 4th, 1975, actors Jon Voight and Marcheline Bertrand had a daughter named Angelina Jolie Voight. Jon and Marcheline separated, and Angelina grew up to become a "punk kid with tattoos" who studied acting. One of her first film roles was in 1995's Hackers, and she married her English co-star Jonny Lee Miller the following year.

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However, the marriage didn't last as 24-year-old wild child Angelina met 44-year-old Billy Bob Thornton on the set of 1999's Pushing Tin. They married after dating for two months.

Brad Dates Half of Hollywood

Meanwhile, Brad Pitt rose to global stardom in hits like Legends of the Fall, Interview With a Vampire, and Seven. And he dated most of his co-stars — from Christina Applegate and Juliette Lewis to Geena Davis, Julia Ormond, Thandie Newton, and Gwyneth Paltrow.

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Perhaps most famously, Brad and his Seven co-star Gwyneth dated between 1994 and 1997. They even got engaged after Brad popped the question on a balcony in a little Argentinian town. However, Gwyneth called off the engagement as she feared she was too young.

Jennifer Aniston

After dating Claire Forlani while making Meet Joe Black and a brief fling with Demi Moore in 1998, Brad's agent set him up on a blind date. The blind date was with another of his manager's clients, Jennifer Aniston, aka Rachel Green from Friends. The two gorgeous actors fell in love and courted for two years.

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They tied the knot on July 29th, 2000, in a lavish Malibu wedding with 200 guests and 50,000 flowers. Brad and Jen were Hollywood's hottest couple… until Angelina came along!