From Billy Bob Thornton to Brad Pitt: A look back at Angelina Jolie's dating history

Angelina Jolie has become almost as famous for her love life as she has for her work as an actress, producer and director.

Eight years after she separated from husband Brad Pitt following allegations of domestic abuse sparked by a dramatic plane ride with their six children, the two are still at war.

But before meeting Pitt on the set of their 2005 film Mr & Mrs Smith, Jolie, now 49, had a colourful dating life, starting with her first love at 14.

Let's take a look back at Angelina Jolie's relationships, including her three marriages and divorces.

READ MORE: Cameron Diaz's star-studded dating history

First love

Jolie first became interested in acting as a child and studied at the Lee Strasberg Theatre Institute while attending Beverly Hills High school.

After being bullied, she changed schools, and began dressing in all black, which coincided with a dark period in her life.

It is around this time Jolie met her first love. She told US Cosmopolitan she was allowed to live with her unnamed then-boyfriend when she was just 14.

"My mother is so caring and nurturing, and the choices she made for me were not irresponsible," she explained.

"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 mum in the next room because I was going to have a boyfriend.

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"She made the choice, and because of it, I continued to go to school every morning and explored my first relationship in a safe way. So in some strange way, she really did the right thing. It kept me out of trouble."

Jolie further elaborated on the relationship during a 2011 interview with The Sun.

"We lived like a married couple for two years. By the time I was 16, I wanted my freedom and wanted to focus on work," she reportedly said.

After the relationship ended, Jolie decided to concentrate on becoming an actress.

Jenny Shimizu

After getting her start in music videos and a few films, Jolie was cast in the film Foxfire as Legs, a mysterious teenage drifter who forms a bond with four local high school students.

One of the other students was played by Jenny Shimizu.

During a 1997 interview with Girlfriends magazine, Jolie said she fell in love with Shimizu instantly.

"I fell in love with her the first second I saw her," she said.

"Actually, I saw when she was being cast in Foxfire, and I thought she had just read for my part. I thought I was going to lose the job. I said to myself, 'Oh, my God, that's Legs'.

"She's great. We had a lot of fun. I probably would have married Jenny Shimizu if I hadn't married my husband."

Jonny Lee Miller

The 'husband' she was referring to was British actor Jonny Lee Miller, of Trainspotting fame, whom she started dating before Shimizu. They met when she was cast in her first major film, Hackers.

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She told Girlfriends in 1997, "We met during Hackers, and then we didn't talk to each other for a long time.

"When I was doing Foxfire we started talking, and months later we got married."

The couple married in 1996, when Jolie was just 20 and Miller was 22.

The bride reportedly wore black rubber pants and a white shirt with the groom's name written in blood on the back. She told The New York Times she used a surgical needle to draw her own blood.

Jolie told Girlfriends she and Miller got matching tattoos during their time together.

"When I got my first tattoo, I got 'death', and Jonny got 'courage'. While he was doing Trainspotting, I was in Scotland and wanted to get another one, but I didn't know what to get, so I just got 'courage'." I thought, 'Oh I'll just match his.'"

During the 1997 Girlfriends interview, Jolie was asked to comment on Miller's resemblance to someone who would figure in her future.

"Your husband has been described as Britain's Brad Pitt. Is that a fair assessment?" the interviewer asked, eliciting laughter from Jolie.

"Really? I don't know Brad Pitt, but that's certainly not how I treat him," she replied.

They split up after 18 months of marriage, with Jolie later admitting she would disappear for days at the end of their relationship.

Billy Bob Thornton

Jolie met Billy Bob Thornton on the set of the 1999 film Pushing Tin, in which they played husband and wife.

Both were in other relationships, with Thornton reportedly engaged to actress Laura Dern.

They married in Las Vegas in May 2000, after two months of dating. Jolie was 24 when she married Thornton, who is 20 years her senior.

Jolie and Thornton were known for public displays of affection, and wearing vials of each other's blood around their necks, which Thornton confirmed in a 2014 interview with The Hollywood Reporter.

"[The] vial of blood is very simple. You know those lockets you buy that are clear and you put a picture of your granny in and wear it around your neck? She bought two of those," he said.

"We were apart a lot [for filming]. She thought it would be interesting and romantic if we took a little razorblade and sliced our fingers, smeared a little blood on these lockets and you wear it around your neck just like you wear your son or daughter's baby hair in one."

By 2002, Jolie was one of Hollywood's highest earning actresses.

In March that year, the couple announced they were adopting a child from Cambodia. Three months later, the marriage was over and Jolie subsequently took over the adoption of Maddox alone.

During a 2012 interview with Nightline, Thornton took the blame for the marriage ending.

"We had a great marriage and I chickened out because I didn't feel good enough. That's all that happened. It was no big deal, we never hated each other."

At the time of her August 2003 Cosmopolitan interview, when asked if she would ever marry again, Jolie replied, "I highly doubt it."

Brad Pitt

In 2003, Jolie was cast in the film Mr & Mrs Smith after Nicole Kidman dropped out. Her co-star was Brad Pitt, who was then married to Hollywood golden girl Jennifer Aniston.

Filming began in January 2004, and rumours soon circulated about the chemistry between the co-stars, who played husband-and-wife assassins out to kill each other.

The shoot was interrupted so the pair could film other projects before resuming in August 2004.

By March 2005, Aniston had filed for divorce and the following month, Pitt and Jolie reportedly vacationed together with Maddox.

Jolie denied anything physical happened before Pitt and Aniston separated but admitted they "fell in love" on set.

She told The New York Times in 2008, "Not a lot of people get to see a movie where their parents fell in love."

In a 2006 interview with Vogue, Jolie said she realised she had feelings for Pitt early in the project.

"I think a few months in I realised, 'God, I can't wait to get to work.' We just found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair."

By the end of the shoot, she said they realised "it might mean something more than we'd earlier allowed ourselves to believe."

After he and Aniston split, things moved quickly. By January 2006, Pitt had legally adopted Jolie's children Zahara and Maddox.

Jolie and Pitt's first child together, Shiloh, was born in May 2006.

The next year, Jolie travelled to Vietnam to adopt Pax, whom Pitt also later legally adopted.

By February 2008, Jolie was pregnant again. Twins Vivienne and Knox arrived in July that year.

The couple got engaged in 2012 and wed in August 2014 in a chapel at their French home. Jolie wore a wedding dress and veil that featured drawings by their children.

They spent their honeymoon filming By the Sea, but less than a year after its premiere, Jolie filed for divorce in September 2016 following a dramatic private plane ride home from Europe.

It later emerged an argument broke out on board resulting in Pitt being investigated for child abuse.

In her divorce petition, Jolie asked for full physical custody of their six children, sparking one of the most drawn out divorce and custody battles in Hollywood history, which still drags on today.

In the years that followed, the couple's older children have turned 18, meaning they are no longer subject to custody orders.

They have made their feelings about Pitt known in other ways.

Pax, then 16, took to social media on Father's Day 2020, blasting the actor.

"You have no consideration or empathy toward your four youngest children who tremble in fear when in your presence. You have made the lives of those closest to me a constant hell," he wrote.

"So, Happy Father's Day, you f---ing awful human being."

Shiloh, who just turned 18, announced her intention to drop "Pitt" from her name in a Los Angeles newspaper in July 2024.

Meanwhile, Zahara, now 19, introduced herself as Zahara Marley Jolie during a 2023 college induction ceremony, while Vivienne, now 15, was listed as Vivienne Jolie on a theatre playbill this year.

In a 2023 interview with Vogue, Jolie said she and their six children "had a lot of healing to do" in the years following the split.

"We had a lot of healing to do. We're still finding our footing," she said.

"I feel a bit down these days. I don't feel like I've been myself for a decade, in a way, which I don't want to get into."