Brad Pitt and Angelina Jolie’s ex’s: Where are they now?

Some of Brad and Angelina’s most famous ex’s help us understand what happens when you split with a Jolie-Pitt.

While tabloids like to pigeonhole the former Mrs Pitt as the poster girl for sad and lonely headlines, seven years since her divorce Jennifer Aniston seems to be kicking goals both professionally and personally. On the film front, by 2010 Aniston’s movies had grossed more than $1 billion worldwide at the box office and she is currently engaged to actor Justin Theroux.

Before Jennifer Aniston Brad had a high profile engagement to Gwyneth Paltrow whom he dated from 1994 to 1997, but the Shakespeare in Love star claims she broke his heart when she ended their engagement. In 2003 Gwyneth, 41, went on to marry British rocker Chris Martin and the couple had two children, Apple, 9, and Moses, 8, before they announced they were ‘consciously uncoupling’ earlier this year. Gwyneth is now reportedly dating Glee co-creator Brad Falchuk.

Angelina’s first hubby was British actor Johnny Lee Miller whom she also met on the set of their 1995 movie Hackers. In an interview with Buzzfeed in 2013 Jolie candidly revealed the little known film reminded her of “Well, oddly, love”. “That’s where I met Jonny,” Jolie said of Miller, “who is still a great friend.” The mother of six added, “I think of him when I think of that. Although, I’m sure the movie looks so ancient now, but we had a lot of fun making that.” Miller currently stars as Sherlock Holmes on hit TV series Elementary and has been married to actress Michele Hicks since 2008. The couple have one son, Buster Timothy Miller.

Angelina Jolie’s bisexuality has never been a secret. The Oscar-winner dated Japanese- American born model Jenny Lynn Shimizu whom she met on the set of their film Foxfire. The relationship was not a fleeting romance for Jolie who told Girlfriends magazine in 1997 “I would probably have married Jenny Shimizu if I hadn’t married my husband. I fell in love with her the first second I saw her.” The 47-year-old model is currently engaged to brand consultant Michelle Harper (pictured) and in June the pair featured together in a bridal shoot for Vogue.

Nowadays it’s pretty hard to imagine that Angelina Jolie, the humanitarian and Earth mother, was once the wild child wife of Billy Bob Thornton. But take a trip down memory lane to the early noughties and you might recall Angie and Billy Bob sporting vials of each others’ blood around their necks as a symbol of commitment or giving red carpet interviews about sexual relations in limos on the way to events. While their union didn’t last – the couple split in 2003 – they have reportedly remained friendly and Angelina has even penned the foreword for her ex-husband’s memoir, The Billy Bob Tapes: A Cave Full of Ghosts. Since his divorce from Angelina Billy Bob has been in a decade long relationship with make-up artist Connie Angland and seems to think that the secret to his decade long romance is not making it official.

After meeting on the set of the TV movie Too Young to Die in 1989 Brad Pitt began dating 16-year-old Juliette Lewis. Of the relationship Brad told People “We were trying to be Sid and Nancy or something,” after the pair moved in together. After starring together as a pair of crooked serial killers in 1993’s Kalifornia the pair split. While Lewis, 41, still is a well sought after actress she tells Page Six her personal life isn’t soaked in celebrity sparkle. “I’m 41. Live in LA. No husband, no kids. Care for my ailing parents. Simple life. Junk food. I’m a naturalist. I love dogs. Chihuahua terrier Teddy, my constant companion, is 8, and I take him everywhere — on tour, on location.”