Along with Maddox, 19, whom Jolie adopted on her own in 2002, and Zahara, 16, whom she adopted in 2005, the two adopted Pax, 17, together, and then had biological daughter Shiloh, 15 and twins Vivienne and Knox, 12, becoming the most notorious family in Hollywood.
Here is a look back at the famous family's growth and memorable moments throughout the years.
Where It All Began
Back in 2005, the same year that the mother of six started dating the Ocean's Thirteen star and future father of her children, Jolie was spotted taking her first two babies, Maddox and Zahara, to visit the local toy store in Malibu.
The Fun Mom
That same year, the film siren took her little son Maddox to a L.A. Toys R Us store where she bought an electric motorcycle and games for daughter Zahara.
Ready To Shop Til They Drop
In 2006, the fun loving mom is seen leaving NANITO, a children's clothing store in Berlin's Prenzlauer Berg, with her son Maddox and her daughter Zahara. At the time, the star was pregnant with her and Pitt's first child together Shiloh, whom they welcome later that year.
Central Park Strolls
Little Zahara was seen out with her mom, both rocking matching white tops, in New York City's Central Park in August of 2007.
Adding To Their Family
In 2007, the gorgeous family was seen leaving their hotel and boarding a boat in the scenic city of Venice, Italy. That same year they welcomed Pax into the family after adopting him from Vietnam.
Day Out With Dad
The hunky actor had his hands full back in 2007 as he left the playground in New York City with Pax and Zahara on each arm and Maddox trailing behind him.
Days Off With The Whole Family
In 2007, on her days off from shooting the 2008 drama The Wanted, the couple brought the family out for a day of fun at a museum in Chicago.
Completing Their Brood
In 2008, the Hollywood power couple completed their family when the actress gave birth to twins Knox Leon and Vivienne Marcheline. Here, the family is pictured in 2010 taking a stroll in Venice, Italy.
A Very Famous Playdate
In 2011, while in London, Zahara, Knox, Vivienne and Shiloh were seen leaving a playdate with another pair of famous kids, Gwen Stefani's sons Kingston and Zuma. Later in 2012, it was revealed that Pitt and Jolie were engaged.
A Family On The Move
Looking extremely elegant in a white button up coat, Jolie landed hand-in-hand at LAX with adorable twins Vivienne and Knox. In 2014, the parents of six married at Chateau Miraval in France. All of the children are involved in the ceremony.
In 2015, Zahara was pictured landing at LAX with her fedora-clad father leading the way. Later in 2016, Pitt and Jolie announced their separation after two years of marriage.
Snowy Fun In Colorado
Despite the looming divorce, in 2017, the Maleficent actress was seen having a fun filled afternoon with her kids, Shiloh and Knox, getting toys and ice cream in Crested Butte, Colo..
Celebrating Knox and Vivienne's Birthdays At Disneyland
The family headed to Disneyland to celebrate twins Knox and Vivienne's birthdays in 2017. Jolie was seen having the best time with Shiloh on one of the rides, despite the custody battle ranging on with her ex-husband.
Working On Films Together And Showing Support
In September 2017, the activist and her kids attended the premiere of First They Killed My Father, a film in which her son Maddox worked on.
Family Movie Day
In 2018, the star and Shiloh, Knox, Vivienne and Zahara had a family day out at the movies in Westwood, Calif..
Shiloh, Vivienne and Knox joined their mom for some holiday shopping at The Grove in LA in 2018. All four seemed to have a fabulous time with shopping bags in hand and smiles plastered on their faces.
A Night Out At The Dumbo Premiere
In March of 2019, all grown up duo Vivienne and Zahara attended the premiere of Disney's Dumbo in Los Angeles with their glamorous mom.
Growing Into Teenagers
An elegant looking Jolie was seen grabbing a bite to eat with her now teenaged kids Pax, Zahara and Shiloh at Fig and Olive in Los Angeles in 2019.
A Family Affair
Five of the 46 year old's six children were on hand to celebrate the release of Maleficent: Mistress Of Evil in 2019. Jolie revealed that she asked all six of her children if they wanted a part in the film, but none of them wanted to partake.
The Gang Is All Together
In August of 2020, amid a crazy year of the COVID-19 pandemic, the whole crew got together for dinner at Nobu.
Girls Day Out
In 2021, Jolie took Zahara and Shiloh out for a girls shopping day in Los Angeles, where the visited a small boutique and stopped for lunch.