HE'S been the world's most eligible bachelor on and off for decades, amid failed romances, engagements and marriages to some of Hollywood's most stunning stars.
And now Brad Pitt is once again on the market, after reportedly splitting from his German model girlfriend Nicole Poturalski, 27.
The 56-year-old actor was first rumoured to be dating the swimsuit model – who is reportedly in an open marriage – in August, after they were seen boarding a private jet together.
However, less than two months later, an insider has claimed to ET that the pair have called it quits – and their relationship was "never a big deal".
It follows a string of failed romances for Brad, who has been engaged to two actresses, married to two more, and enjoyed some surprising flings since beginning his Hollywood career.
Now, after admitting his personal life has been a "disaster" on an episode of WTF with Marc Maron podcast earlier this year, we look at how he has become the world's most eligible bachelor once again…
Asked agent to arrange date with Sinitta
After she split up with Simon Cowell in the 80s, Sinitta began dating Brad Pitt – and they went on to enjoy a two-year relationship.
According to the X Factor regular, 52, Brad got his agent to call hers after spotting her on TV – and it went from there, with the pair even attending the 1988 Smash Hits Poll Winners Party together.
Sinitta happily opened up about the fling when she appeared on I'm A Celebrity, telling her campmates about his "hot" physique.
"He was beautiful with the most amazing body," she said. "I saw him for two years. He was fun, he was young and very sweet.
"Some ardent fan gave me a slap when I came out of a supermarket over that relationship!
"It was before he made Thelma And Louise but even I saw that movie and thought: 'Oh my God, what have I done?'"
'Caught in bed' with Mike Tyson's ex wife
After his romance with Sinitta broke down, Brad went on to enjoy a fling with Mike Tyson's ex wife Robin Givens, 55, shortly after their break-up.
And the boxer has sensationally claimed he found out all about how intimate they'd got in the worst possible way.
Tyson, 54, alleged he walked in on the pair in bed together, and described in detail how a panicked Brad begged him not to hit him.
He claimed in his 2013 memoir, Undisputed Truth, that Brad said: "Dude, don't strike me," when he saw him.
He also told a US radio show: “I was mad as hell. You should have saw his face when he saw me.”
However, Robin has since disputed her ex's claims and said on Watch What Happens Live with Andy Cohen that he only saw them in a car together.
She added: "I thought he said he caught us in bed. I didn’t read the book, but I was told he said he caught us in bed, which never happened. Never, ever."
Ditched by Christina Applegate at VMAs
Early in 1989, Brad enjoyed a brief fling with Christina Applegate, with the pair even attending the MTV VMAs together – albeit, briefly.
Christina, 48, who famously played Brad's ex wife Jennifer Aniston's sister on Friends, revealed she ended it when she left the date to meet another man, during a chat on Watch What Happens Live.
When host Andy Cohen asked: "You ditched him for another guy. The question is, who was the guy you ditched Brad Pitt for?"
The actress replied: "I have to say it? I don't have to do nothing!" However, she went on to confirm the other man wasn't an actor.
Engagement to Jill Schoelen
Brad began dating The Stepfather star Jill Schoelen, 57, after meeting on the set of the horror movie Cutting Class – before they enjoyed a three-month engagement in the late 80s.
However, he has claimed she eventually broke it off when he visited her in Budapest, Hungary, while she was filming The Phantom of the Opera.
He told The Sun of the break-up: "She called me up in Los Angeles and was crying on the phone.
“She was lonely and there was a huge drama. At this point I had $800 (£613) to my name and I spent $600 (£460) of it getting a ticket from Los Angeles to Hungary to see her.
"I got there, went straight to the set where she was filming and that night we went out to dinner.
“She told me that she had fallen in love with the director of the film. I was so shocked I said, 'I'm outta here'."
'Wonderful' relationship with Juliette Lewis
Brad enjoyed a longer relationship with actress Juliette Lewis from 1989 to 1993, when he was 27 and she was a teenager, after growing close while filming their movie Too Young to Die.
The pair also went on to appear in 1994 film Kalifornia by each other's side.
They spent a few years together before eventually splitting in 1993.
Juliette, 47, has since opened up about the relationship to the Mail on Sunday, saying: "It amazes me that people are still fascinated that we went out for four years.
"I was a teenager at the time. It's a lifetime away. I was in my high-school years and it was a wonderful, loving relationship with a fun, smart guy. Then it was over and he went on to become incredibly famous."
Engagement No.2 to Gwyneth Paltrow
His engagement to Jill didn't last long at all, and sadly Brad didn't have much more luck with his second – to actress Gwyneth Paltrow.
The pair grew close while filming thriller Se7en in 1994, and appeared head over heels – as Gwyneth gushed at the time: "I am properly in love for the first time in my life… and I do not care if my former boyfriends read this."
They got engaged in 1996, but it appeared to be the kiss of death for their relationship, as it all fell apart the following year.
Gwyneth, 48, has since revealed she got cold feet in an interview on The Howard Stern Show, saying: "I think I was a kid and I wasn't ready. He was too good for me."
She also admitted she was heartbroken after their split and told Vanity Fair: "It really changed my life. When we split up, something changed permanently in me. My heart sort of broke that day, and it will never be the same."
Marriage to Jennifer Aniston
One of Brad's most high profile relationships began around a year later, when he started dating Friends star Jennifer Aniston, after meeting on a blind date set up by their agents.
They made their red carpet debut as a couple at the Emmy Awards in 1999, before confirming they were engaged later that year – by jumping on stage at a Sting concert to show off Jen's ring.
The pair married in a private wedding ceremony in Malibu in 2000, and they seemed to go from strength to strength from there – with Brad even making a guest appearance on Friends as Rachel's former enemy.
In an interview with W magazine in 2003, Jen, 51, said of her husband: "He’s certainly a big love in my life… And I know that we have something special, especially in all this chaos.
"In this nutty, brilliant, wonderful, hard business that we have, it’s nice to have somebody who’s anchored and knows you, really knows all of you."
However, much to the shock of their fans around the world, the pair split in 2005 amid claims Brad had grown close to Angelina Jolie while filming their hit Mr and Mrs Smith.
Brad always denied he cheated with Angelina.
Marriage No.2 to Angelina Jolie
Following a string of affair rumours, Brad and Angelina's romance was eventually confirmed in April 2005 when they were spotted on holiday in Kenya with her adopted son Maddox – three months after he and Jen announced their divorce.
The photos left Jen heartbroken and she told Vanity Fair afterwards: "The world was shocked, and I was shocked."
The pair continued their jet-setting lifestyle from there, and, asked later why Mr and Mrs Smith had become his favourite film, Brad told Rolling Stone: “Because I fell in love.”
The pair kept their relationship fairly private for the first year, but finally acknowledged it in 2006 when Angelina, 45, revealed she was pregnant.
Brad applied formally to adopt Angelina’s kids Maddox and Zahara, before she gave birth to their first biological child, Shiloh, in Namibia in May 2006.
The couple adopted another child, Pax, from a Vietnamese orphanage in 2007, before welcoming twins Knox Leon and Vivienne Marcheline the following year.
They married in 2014 at their Chateau Miraval in France, with all six of their kids very involved in the ceremony. Later that year, they revisited the start of their relationship by working on another film together, By The Sea.
However, it all came to a sudden end in 2016 when Angelina filed for divorce, citing "irreconcilable differences" and requesting primary custody of their kids. The pair are still in a custody battle now.
The two have been co-parenting their children "amicably" thanks to "family therapy", however, and a source told People: "They definitely needed help figuring out all the child-custody issues and how Brad could be a dad again.
"Since the kids are older now, they are no longer dealing with separation issues from Angie."
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