Angelina Jolie Details "Very Dark" Period Away From Hollywood

Having fallen in love with the country of Cambodia while filming 2001's Tomb Raider, Angelina Jolie paid a visit to an orphanage in the provincial town of Battambang in the hopes of finding her first child.

Walking through, "I didn’t feel a connection with any of them," she later told Vanity Fair, until she saw Maddox—born Aug. 5, 2001—lying in a box suspended from the ceiling. Feeling that bond in an instant, she said, "I cried and cried." 

Though the then-26-year-old adopted her eldest son as a single mother, after she began dating future husband Brad Pitt, he started the process to adopt him as well. 

Thanks to an interest in his mom's work, when Angelina directed 2017's First They Killed My Father, the film adaptation of her friend Loung Ung's book about the Cambodian genocide by the Khmer Rouge regime, Maddox signed on as executive producer. “I was trying to help wherever I could,”" he told People of the role. As for his boss, aka mom, she's "fun, funny, and easy to work with,” he said. "She’s a wonder."

After studying biochemistry at South Korea's Yonsei University (a choice his mom said she "could not be happier about"), Maddox attended a state dinner at the White House in April 2023 when President Joe Biden and First Lady Dr. Jill Biden hosted South Korean President Yoon Suk Yeol and First Lady Kim Keon Hee.

Born on Nov. 29, 2003, "He spent three-and-a-half years of his life in one place, in one room, in this one little iron bed with 20 other kids, and having no choice for himself to do things, having no freedom," Angelina told MSN in 2007 of Pax's early years in an orphange outside Ho Chi Minh City, Vietnam.

Living with Maddox and sisters Zahara and Shiloh, "suddenly, here he is in a very free situation with new brothers and sisters and a mom and dad," Angelina continued. "He’s learning English and he’s so loving and he’s wild and free 'cause he suddenly has freedom so he’s a little wild and crazy. But what a tough, remarkable little person."

With an interest in the family business, Pax voiced the character Yoo in Angelina's animated 2016 film Kung Fu Panda 3 and served as set photographer on First They Killed My Father before attending the 2018 Golden Globes with his mom. 

He also helped decorate Atelier Jolie, a creative fashion collective and alteration company Angelina opened in NYC, and worked in the assistant director department on the Italian set of her upcoming film Without Blood.

As Angelina told People of working with both Pax and Maddox, "When a film crew is at its best, it feels like a big family, so it felt natural."

Then-3-year-old Maddox accompanied Angelina to the Hawassa, Ethiopia orphanage where she met eldest daughter Zahara, born Jan. 8, 2005. "Mad loves her," the actress later told Anderson Cooper. "When Z came home she was older, she was seven months old, so for Mad it’s like having this tiny pet he can just hold and look at."

Like her siblings, Zahara has expressed interest in all facets of her mother's work, attending red carpets, launching her charitable Zahara Collection jewelry line in collaboration with jeweler Robert Procop in 2019 and making trips to Syrian refugee camps as part of her mom's efforts with the UNHCR.  

In August 2022, Angelina grew emotional while dropping Zahara off at Atlanta's Spelman College ("I haven't started crying yet so…hopefully I can hold it together," she shared in an Instagram video), later returning for the HBCU's homecoming festivities. 

Zahara—who joined the school's Alpha Kappa Alpha sorority in 2023—has also accompanied the actress on several trips to Washington, D.C. She was by Angelina's side when she gave a tearful speech promoting the renewal of the Violence Against Women Act in February 2022 and a year later when they met with lawmakers to advocate for the passage of the Justice for All Reauthorization Act of 2022.

Months after announcing her pregnancy, Angelina and Brad welcomed Shiloh at Cottage Hospital in Swakopmund, Namibia on May 27, 2006. "Shi’s so full of light and love, she’s just a little honey, and very, very funny," Angelina said in her MSN interview. "I think I’m recognizing some of myself in that one—she’s going to be a little bit of trouble!"

Making her red carpet debut at the Unbroken premiere in 2014, Shiloh went on to appear at events for Maleficent: Mistress of Evil, The Breadwinner and Dumbo, the 2018 National Board of Review Awards Gala and the 2021 Eternals red carpet, where she wore Mom's Dior gown.

"I'm like, 'Oh my god, wear it and wear it better than me!" Angelina told E!'s Daily Pop of encouraging her kids to raid her closet. "And take it, and it's your turn, anything.' I'm that mom."

In addition to showing interest in Angelina's humanitarian efforts, Shiloh seems to have taken a few steps into the entertainment industry, spending time at L.A.'s Millennium Dance Complex. 

On her 18th birthday in 2024, the teen submitted a petition at a Los Angeles Court to remove the hyphenated "Pitt" part of her surname to be known as Shiloh Nouvel Jolie. A source close to the matter told E! News Shiloh had hired her own lawyer and paid for it on her own. 

Debuting her baby bump at the 2008 Independent Spirit Awards, Angelina later gave birth to Knox and then his twin sister Vivienne in Nice, France, on July 12, 2008. Settling in at their Château Miraval, “It is chaos, but we are managing it and having a wonderful time,” Angelina told People soon after, adding that Shiloh and Zahara liked to choose the twins' clothes "and help change and hold them."

Named for Brad's grandfather, Hal Knox Hillhouse, Angelina noted that “Knox is a lot like Brad, emotionally and physically." And, indeed, the pair did bear a striking resemblance while attending the 2015 British motorcycle Grand Prix.

Like older siblings Pax, Zahara and Shiloh, Knox took on a small role in 2016's Kung Fu Panda 3, voicing the part of Ku Ku. "They were kind of shy," Jolie told ET. "They don't really want to be actors, but I didn't want them to miss the opportunity. They came in, and they had a lot of fun with it."

Knox's younger-by-a-minute fraternal twin "reminds me of my mother in that she isn't focused on being the center of attention but in being a support to other creatives," Angelina told E! News in a statement, referring to her late mom Marcheline Bertrand. "She's very thoughtful and serious about theatre and working hard to best understand how to contribute."

Though she nailed her role as the younger version of Elle Fanning's Aurora in 2014's Maleficent ("I was actually shocked that she was doing so well she went back and hit her mark! It's frightening," Angelina said at the time), the high schooler has since gravitated toward behind-the-scenes roles. 

Angelina said that Vivienne was the one to encourage her to help bring an adaptation of Francis Ford Coppola’s 1983 film The Outsiders to Broadway, so the teen ended up serving as a volunteer assistant to her producer mom on the Tony winner. 

“She’ll correct me," Angelina told People of Vivienne, who's credited in the playbill as Vivienne Jolie. "She'll say, 'Didn't you read the memo? We have to do this, we have to go through this,' ” Jolie said. “She’s been a really tough assistant. She takes it very, very seriously.”