The bizarre history of Angelina Jolie’s love life

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’.

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!’

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 roo m 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.

‘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.

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.

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.

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.

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.