She once claimed to have slept with only four men - three of whom were her husbands.

But Angelina Jolie has experienced a more bizarre sexual history than anything Hollywood could dream up.

The 41-year-old shocked the world on Tuesday when she filed for divorce from her husband of two years Brad Pitt, citing 'irreconcilable differences'.

Racy past: Angelina Jolie had a romance with Jenny Shimizu and the pair starred together in 1996's Foxfire. 'I probably would have married Jenny if I hadn't married my husband,' Jolie revealed in an interview years later. 'I fell in love with her the first second I saw her'

But it was only the latest chapter in a very colourful tome, which appears to have started as far back as preschool.

'I was a member of a group called the Kissy Girls. I was very sexual in kindergarten,' she told OK! Magazine in 2007.

'I created a game where I would kiss the boys and give them cooties. Then we would make out and we would take our clothes off. I got in a lot of trouble!'

The end: Angelina Jolie's shock split from Brad Pitt on Tuesday was just the latest chapter in a very colourful love life story

Jolie lost her virginity at 14 — with her mother's blessing.

'When I was 14, I was either going to be reckless on the streets with my boyfriend or he was going to be with me in my bedroom with my mom in the next room because I was going to have a boyfriend, ' she revealed to Cosmopolitan in 2003.

Things then took a darker turn for the teen, who had a history of self harm and an adolescent fascination with knives.

Number one: She met first husband-to-be Jonny Lee Miller on the set of 1995's Hackers

'I had started having sex with my boyfriend and the sex and the emotions didn't feel enough. I was no longer a little girl,' she told OK.

'In a moment of wanting to feel closer to my boyfriend I grabbed a knife and cut him. He cut me back.

'We had an exchange of something and we were covered in blood, my heart was racing. Then whenever I felt trapped, I'd cut myself. I have a lot of scars. It was an age when I felt adventurous and after a few beers things happened.'

Switching sides: She split from the Brit when the film wrapped, which led her to her first same-sex relationship with model-actress Jenny Shimizu (bottom right), whom she met on the set of 1996's Foxfire

The by age 20, the actress had done 'just about every drug possible', including cocaine, ecstasy, LSD and 'my favourite, heroin'.

She credited her first husband Jonny Lee Miller with steering her away from her 'dark days'.

The two met and began dating on the set of their 1995 film Hackers; she later claimed this was her first sexual relationship since her first boyfriend.

Back on: It was while filming Foxfire Jolie reconnected with Miller, eventually marrying in March 1996

He would also be the first of many of her co-stars with who she would have both rumoured and real-life relationships.

She split from the Brit when the film wrapped, which led her to her first same-sex relationship with model-actress Jenny Shimizu, whom she met on the set of 1996's Foxfire.

'I probably would have married Jenny Shimizu if I hadn't married my husband,' Jolie revealed in an interview years later. 'I fell in love with her the first second I saw her.'

It was while filming Foxfire Jolie reconnected with Miller, eventually marrying in March 1996.

Gross: She caused a stir when she was pictured kissing her brother Haven full on the lips backstage at the 2000 Golden Globes, doing the same three months later on the Academy Awards red carpet

She attended her wedding in black rubber pants and a white T-shirt, upon which she had written the groom's name in her blood.

However Shimizu later claimed that she and Jolie continued to hook up for years afterward.

'Angelina and I had a really wonderful relationship that lasted many years,' she said. 'I was dating her while she was seeing other people - she was that type of person; wonderful and open.'

Jolie filed for divorce from Miller in February 1999.

Close family: After picking up her first Oscar - Best Supporting Actress for Girl, Interrupted - she opened her acceptance speech by telling the crowd 'I'm so in love with my brother right now'

The following year she caused a stir when she was pictured kissing her brother Haven full on the lips backstage at the 2000 Golden Globes, doing the same three months later on the Academy Awards red carpet.

After picking up her first Oscar - Best Supporting Actress for Girl, Interrupted - she opened her acceptance speech by telling the crowd 'I'm so in love with my brother right now'.

That month she began dating Billy Bob Thornton, and two months later they married in Las Vegas.

The pair had met the previous year on their film Pushing Tin, in which she plays his young wife who cheats on him with rival John Cusack.

Number two: That month she began dating Billy Bob Thornton, and two months later they married in Las Vegas

Angelina and Billy Bob reportedly did not pursue a relationship during filming, as he was engaged to actress Laura Dern at the time, while she was rumoured to be dating yet another co-star: Timothy Hutton, with whom she appeared in 1997's Playing God.

Jolie and Thornton - who is 20 years her senior - frequently made headlines with their frequent and outlandish declarations of love, including her massive 'Billy Bob' tattoo on her shoulder.

The couple also famously wore vials of each other's blood around their necks.

In 2002 they announced they were adopting a child from Cambodia, but split suddenly three months later.

Love is: Jolie and Thornton - who is 20 years her senior - frequently made headlines with their frequent and outlandish declarations of love, famously wearing vials of each other's blood around their necks

On set again: The pair had met the previous year on their film Pushing Tin, in which she plays his young wife who cheats on him with rival John Cusack

'It took me by surprise, too, because overnight, we totally changed,' she said at the time. 'I think one day we had just nothing in common.'

She also said in the same interview that she wouldn't 'even consider a relationship for another seven, eight years' - but that did not prove to be the case.

In 2005 she was accused of being the reason behind Brad Pitt's split from wife Jennifer Aniston, when the two reportedly hooked up while filming Mr And Mrs Smith.

Jolie denied it at the time, but did admit she 'fell in love' with him while filming.

Taken: Angelina and Billy Bob reportedly did not pursue a relationship during filming, as he was engaged to actress Laura Dern at the time

And another! Meanwhile she was rumoured to be dating yet another co-star: Timothy Hutton, with whom she appeared in 1997's Playing God

'To be intimate with a married man, when my own father cheated on my mother, is not something I could forgive,' she said in an interview with Today that year.

'I could not look at myself in the morning if I did that. I wouldn't be attracted to a man who would cheat on his wife.'

However their relationship status was confirmed in 2006 when she announced she was pregnant with his child.

After seven years and six children together they announced their engagement in April 2012, and married on August 23, 2014.

Drama: In 2005 she was accused of being the reason behind Brad Pitt's split from wife Jennifer Aniston

Despite rumours she had linked up with other co-stars throughout the years - including both Colin Farrell and Jared Leto during the filming of Alexander - Jolie has claimed she only slept with four men in her life; three of whom she married.

However, she appeared to contradict this in a New York Post interview in 2004, in which she confessed having numerous 'friends with benefits'.

'I went for about two years with absolutely no man around me and then decided to get closer to men who were already very close friends of mine,' she said at the time. 'It's kind of an adult way of having adult relationships.

Pattern: The two reportedly hooked up while filming Mr And Mrs Smith

'As crazy as that sounds, meeting a man in a hotel room for a few hours and then going back and putting my son to bed and not seeing that man again for a few months is about what I can handle now.'

'I can feel like a woman and get close to a man, but it's not a relationship that interferes with my family,' she added.

'I've never had a one night stand in my life - these are people that I know very well.'