Angelina Jolie and Brad Pitt - popularly known as Brangelina - shocked the world on Tuesday (Sept 20) with news of their split, when Jolie's lawyer said she had filed for divorce, and cited their separation date as Sept 15.

During the 10 years they spent together, they had six children - three biological and three adopted.

Here's the timeline of how each child came into their lives, starting first with the oldest, Maddox.

1. Maddox Chivan Jolie-Pitt, 15

The first and oldest child of Brangelina, Maddox was adopted in 2002 from Cambodia, when he was less than a year old.

He is calm around the paparazzi like his parents are.

Jolie has touted him as being interested in pursuing a film-making career.

Maddox took on the role of a production assistant in the 2015 movie By The Sea, a film written by Jolie and co-produced by Pitt and Jolie herself.

Though his role is still undefined, he will be taking part in Jolie's project with Netflix this year, an adaptation of First They Killed my Father: A Daughter of Cambodia Remembers.

2. Zahara Marley Jolie-Pitt, 11

Out of all the six children, Zahara had it the toughest before Jolie and Pitt adopted her while she was suffering from malnutrition and other ailments.

She is known for her brooding stare when photographed by the paparazzi.

Her biological mother revealed that Zahara had been conceived during rape, and that she had been unable to raise her, so she was glad that Zahara was fortunate enough to be adopted by Jolie.

3. Shiloh Nouvel Jolie-Pitt, 10

The first biological child of Jolie and Pitt, Shiloh is described by her mother as a tomboy who is "hysterically funny" and "one of the goofiest, most playful people you'll ever meet".

Shiloh has reportedly asked to to be identified as male, and as Jolie stated in a 2010 Vanity Fair interview, Shiloh told her that she "wants to be a boy".

Shiloh has been inspired by her mother's humanitarian work, and accompanied her to visit Syrian refugees in Turkey in 2015.

4. Pax Thien Jolie-Pitt, 13

An orphan from Vietnam, Pax Thien was born in 2003 and adopted in 2007 by Jolie.

The only child of Brangelina that was not with them from birth, Thien used to fret when the paparazzi were around. Now, he has become less shy and is not so afraid of them.

5. Knox Leon Jolie-Pitt, 8

Born with his twin sister in France, Knox is known as a mama's boy who stays close to Jolie when they are out together.

He was named after Pitt's maternal grandfather, Hal Knox Hillhouse.

Knox's baby pictures, as well as those of his sister, were released to the press in 2008 for US$14 million (S$19 million), the most costly baby pictures at the time.

6. Vivienne Marcheline Jolie-Pitt, 8

Some may recognise her as the young Aurora in Jolie's 2014 movie Maleficent.

It was most apt that her debut movie role was one of a princess, as Vivienne has a love for princesses and the colour pink.

Her parents said she was natural on screen, and this may mark the start of a successful acting career for Vivienne.

Sources: Vanity Fair, Heavy.com, Life and Style Mag, Morning Ledger